The Do’s and Don’ts of Online Dating

In the car I just can’t wait,
to pick you up on our very first date
Is it cool if I hold your hand?
Is it wrong if I think it’s lame to dance?
Do you like my stupid hair?
Would you guess that I didn’t know what to wear?
I’m too scared of what you think
You make me nervous so I really can’t eat

– “First Date”, by Blink 182

So you’ve picked the online dating site or sites that you would like to join, you’ve created what you think is a fabulous profile, you’re getting “winks”, “nudges”, communication requests or emails from potential matches; you might have even shared a phone call with one or two of them, and you’re starting to think that maybe someone long-term could possibly be just around the corner. Maybe you are right, but then…maybe you shouldn’t be too hasty about pinning your hopes on the first potential who crafts a good email or talks a good game.

This portion of my online dating series is about setting expectations somewhere in the realistic realm and avoiding some of the pitfalls that can be encountered during the early days of online dating. All of this is, of course, assuming that you are serious about meeting someone “serious”, and assuming that you don’t luck into Prince (or Princess) Charming immediately. 😉

I was given quite a bit of advice from Wayne when I started this Online Dating Site experiment, and I also received some good tips from eHarmony and tech guru Jon Westfall; I’ll pepper those nuggets throughout this writeup, and let you know about all the different ways that I either did or didn’t follow their wisdom.

Here are a few common overall rules for successful online dating. These rules aren’t absolute, people who break them can find success. Following the rules generally helps to stack the odds in your favor.

The whole purpose of online dating is to evaluate someone for a potential relationship (usually long term). This is done via meeting face to face. Until you meet someone you have no idea whether you’d be compatible for a long term relationship. Extended email, instant messenger and phone relationships – without meeting in person – don’t fall under the typical definition of online dating. A good rule of thumb is 3 to 6 email exchanges followed by one or two phone conversations – then meet face to face.

That’s right – you must get yourself out from behind the keyboard and in front of the person you are considering dating. And the sooner the better. – Wayne

It’s interesting to note that I was in absolutely no hurry to follow Wayne’s rules about spending time with anyone when I started this experiment, and make no mistake about it – it was just an experiment. I was gung-ho about email exchange, maybe even participating in a phone call or two, but I wanted to keep the actual meeting somewhere in the far-off and murky future. That’s probably because, if the truth be told, I wasn’t really interested in dating anyone just yet. There; I said it.

But it would seem that things never work out the way you plan, and it would also seem that when you aren’t really looking for something, you are more likely than ever to find it.

But I digress…

As I may have mentioned (or at least alluded) in my first installment, the sites I joined were eHarmony and Yahoo Personals.

Meeting face to face is nerve wracking. People come up with all sorts of inane excuses to put it off. If your online date suddenly disappears just prior to meeting – don’t take it personally. This is common with online dating. If you do online dating long enough you’ll encounter plenty of folks who just disappear and stop writing back to you during an online process that you felt was progressing well. Get used to picking yourself up and moving along to the next prospective date.

Avoid prolonged communications before you’ve met. This serves to drive up your expectations of the other person to a level that usually can’t be met.

Well at least I didn’t fall into a prolonged communication scenario with there’s one thing Wayne can’t chastise me for; but believe me – he would have other opportunities. 😉

Too much early communication is the #1 mistake new online daters make. There’s nothing worse than emailing and calling someone for three months (or longer) – and then meeting in person and finding out that their pictures were totally unrealistic, old or misleading. Often the chemistry you feel online will not translate to an in person meeting. Realize that this HAPPENS TO EVERYONE. Do not take failure personally in online dating.

My rule of thumb is never to continue contact with someone who does not supply a photo. You should be able to ask them once for the photo and it should be supplied without further prompting. Don’t get suckered into extended contact without seeing a photo. The most common excuse people give is that their camera is broken. Disposable digital cameras are sold at CVS for under $20. There’s no excuse for anyone sophisticated enough to post an online photo not to have a picture. Period. Disobey this rule at your own peril. It’s perfectly acceptable (in my opinion) to ask for a photo and discontinue all further communication if one isn’t readily supplied. – Wayne

Maybe I am just wired differently than most, or maybe it’s because I wasn’t too seriously looking, but as long as a guy included at least one photo where he was looking right at the camera, had a winning smile, and his profile seemed halfway interesting, I wasn’t turned off. But mindful of Wayne’s advice, and not wanting to waste a lot of time with photo-less “matches”, I made it an early rule to delete any potentials who didn’t supply at least one photo in their profile.

I never read a profile that was so good that I was even remotely tempted to ask for a photo when there wasn’t one, but I read plenty of profiles that were meh and would have been deleted without the accompanying photo of their smiling owner.

I never initiated contact with anyone, and I advanced to “open communication” via the eHarmony guided communication process with a total of three people. Yahoo was a little bit different: I had joined and created my profile – basically plagiarized from the one I had created for eHarmony, but I had set my profile so that no one could see it unless I initiated contact with them first; I did this with one person.

Perhaps part of the reason I could afford to be so picky was that I was getting a solid 10 – 15 potential matches each night from eHarmony, with four or five communication requests daily, so I never felt the need to look for any more willing participants.

Did I mention that checking your matches and communicating with them is a major time-suck? Well, it is. 😛

Always look for a recent photo – including a full length body shot. Photos that obscure portions of the person behind an object usually indicate that you’re going to be surprised when you meet. I’ve seen photos of people hidden behind trees, cars, sofas, stone walls, signs, other people, etc. The clearer and more recent the photos look – -the better the odds of a successful first meeting. – Wayne

I did encounter one potential who gave me all sorts of excuses about sending a current full-length photo, but he was also the same guy who offered to drive a couple of hours out of his way to come and meet me for lunch a couple of weeks after we had started talking. He even joked that if I didn’t like what I saw, I could sneak right back out of the restaurant; I don’t think I would ever be that cruel, though. So granted, I was disobeying Wayne by not demanding a full-length photo, but I didn’t feel in this case that I was really setting myself up for a major disappointment.

Be very careful when online. You should never reveal too much personal information (address, cell phone number) until you’ve known someone for a period of time and met them in person. – Wayne

I couldn’t help but nearly blow this one with anyone I got to the “open communication” stage with (meaning we could send emails or call if we wanted to); thankfully there were only three on eHarmony and one on Yahoo that this happened with before I quit.

General overall ratios:

Using Match I found it would take perhaps 10 email conversations to result in 4 phone conversations leading to 3 in person meetings of which 1 – 2 in person meetings would result in a date. These results are just my experience and based on comparisons in other online forums they seem fairly typical. Note that of 10 initial conversations only 4 make it to the phone stage (typically the last step before moving to an in person meeting). This is because a high number of people disappear during the email stage for whatever reason. – Wayne

I didn’t use Match, so I can’t comment, but I did find the process to move along fairly quickly through eHarmony. I think it generally took about three days to hit open communication with the three guys I actually made it with.

Since I was trying to be as honest as possible, I immediately told every guy that I communicated with that even though I was writing an article about the experience (and yes, I mentioned this site), I was genuinely looking for a potential match as well – even if I wasn’t very hopeful.

We strongly encourage you to be cautious when sharing personal information that could reveal your identity. Our Open Communication system will let you communicate while remaining safely anonymous. Don’t give out your name, e-mail or phone number until you feel you have truly gotten to know someone. Once you’ve given out personal information, you cannot take it back! We encourage you to use our anonymous communication system until you are ready for the next step: Talking by phone.

Speaking by phone to the other person is also a critical requirement in getting to know each other better. Before you share phone numbers make sure you have discussed the need to respect each other’s privacy, and if either of you decide to end communication in the future, you will not use the phone number as a means to pursue an unwanted relationship. Most people prefer the man to offer his phone number to the woman and that she initiate any future phone calls, but you decide. Keep the first call to a short duration of 15 minutes or less. – eHarmony

One of the three eHarmony guys, I’ll call him P., asked for a bunch more pictures the minute we hit open communication, and then he started asking highly personal questions, which totally turned me off; I mean, it’s not like you can’t find pictures of me all over the web as it is – even candids with no makeup and bedhead if you look hard enough – and jeez dude, slow down a minute, okay? It’s not a “getting to know you” race. It wasn’t any surprise to me that this was the one guy who seemed to have a problem with me writing about the dating experience, and I closed that relationship quickly.

Avoid profiles or individuals that place a high premium on physical attributes or photos. While it is certainly alright to have certain physical criteria you find attractive and favorable in a mate, it would be unwise to completely rule a person in or out based on their looks. Be especially concerned with individuals that focus solely on looks and have very little substance in their profiles when it comes to what they like or dislike, how they feel about certain topics, or what they’re looking for in a mate. Lastly, sexual innuendo or outright sexual verbiage (e.g. “I can ___ your ____ like no one else you’ve ever met!”) should be an immediate sign of immaturity. – Jon

Interestingly enough, I received a communication from eHarmony about him two days ago, saying that they had deleted his account. I wasn’t exactly surprised. 😛

eHarmony relies on the complete honesty of our users to create our compatibility profiles. Our system works hard to screen-out applicants who are not truthful. However, it is ultimately your responsibility to decide if someone is being truthful and honest. Don’t ignore your instincts and please don’t depend totally on eHarmony for evaluating a person you’ve been matched with. As with people you may meet under any circumstances, your judgment and instincts are necessary to protect yourself from deceitful individuals.

Here are some signs to consider: Watch out for someone who asks for money, uses vulgar language, asks inappropriate questions, or suggests sexual fantasies. Be careful of those who want to speed up the pace, tell you how to run your life, tell stories with inconsistencies, give vague answers to specific questions, urge you to compromise your principles, blame others for their troubles or are always speaking romantically. These are just a few of the signs you may want to think twice about before continuing. – eHarmony

I didn’t reach open communication with the guy who wrote the following missive, you’ll notice that it is tightly written with hardly any spaces; that’s because he fit it into one of the responses of the five intro questions I sent during guided communication. On the off-chance that any of it is true, I have removed any names or geographic locations. But tell me if this missive wouldn’t freak you out if you got it…

Hello Judie, I must tell you some things about me.My late wife had brain cancer.She passed away last month.We found out in December that she was sick.The company that I work for gave me off seven weeks with pay to be with her.I spent the last four weeks on a cot next to her Hospice bed.We talked about a lot of things during those four weeks.We have a ten year old daughter.She has Aspergers.we decided for her well being that she live with her brother in [redacted].For a more stable way of life than I could have offered.I work in the oilfield here.I am on call 24 hours a day and I work 12 days on and 3 days off.Sometimes I’m gone for 2 to 3 days.It would have been very hard on [my daughter].[Redacted], my late wife and I even talked about what I was going to do after she was gone.The two things she made me promise was when I was ready that I would not be alone.That I was to find somebody to be with.She made me promise that when I was ready that I would join Eharmony to find somebody.I know in my heart that I am ready to move forward.I will always love [redacted].I am not looking to replace her.I am looking to find my best friend and companion.I hope we can talk more.If not Jodie I will understand…[redacted]

Ummm…yeah. Thank you for raising more than a few red flags and very nearly creeping me out, dude. 😛

Use good judgment when evaluating profiles, and listen to your gut if something seems wrong. Ever get the creeps when reading something? Perhaps it’s a scary novel, or your roommate’s grocery shopping list, or even an online dating profile. Listen to your gut if you feel something is wrong. If you feel that perhaps he is too inviting when he mentions you can stay the weekend at his secluded cabin, or that she is a bit dodgy when you ask about previous relationships. More often than not your gut can be picking up on many subtle and important aspects of a person. – Jon

I eventually reached the phone call stage with one eHarmony guy – I’ll call him M., and when we spoke for the first time we wound up talking for almost five hours. Somewhere in the middle of that marathon conversation I realized that we were never going to work out, but I still got a kick out of talking to him because we basically hashed out every flaw we thought we had, we discussed almost every failed relationship we had each had – as well as our opinions on why, and we worked out what we were really looking for in a potential mate and how hard we thought it was going to be to ever find that person. So in other words, we both essentially got five hours of therapy for free with a sympathetic stranger, and it was all very nice and non-threatening. At the end of the conversation, I honestly didn’t expect to ever hear from M. again; I mean, hadn’t we just broken every rule by vomiting too much information all over each other?

A few days later he called and said he wanted to come see me. Ack!

Almost as if in answer to a dare, I said “Fine”.

He was the guy I would wind up not meeting because I had started dating someone else; this was probably a good thing for both our sakes.

Someone online should never ask you for money. A common online scam is for someone to appear “just perfect” in a profile and subsequent email conversation – and then suddenly have to “go overseas on business”. Some daters have reported unexpectedly being asked to wire money to their online friend under the guise that the person is “stuck” overseas and for some reason does not have access to money. If this happens to you report the person immediately to the online dating site and discontinue all communication (most dating sites will let you block people from communicating with you). – Wayne

Wayne sent me this advice fairly early on, and certainly after I knew that Sarah and I would be going to Paris at the end of June. I almost felt shady when I mentioned it on the phone to M.; but then I got over it. 😉

One thing I did discover on eHarmony was that I wasn’t the only one who might not be ready (or willing) to enter a dating relationship just yet. In case you haven’t noticed, serious relationships aren’t easy; they take cultivating, time, perseverance, and can basically be a lot of work – even if the payoff is huge in the end (ie. – a happy match). The thought of starting over again can be daunting, even if the anticipated result is extremely desirable; you have to be ready to expend the effort and give the process a fair chance. As unsure as I was about whether or not I was ready to try for a new relationship, I met someone who was even more unsure. With that in mind, I’ll tell you about my last eHarmony potential, S.

Always be respectful and treat your matches as you would want them to treat you. Not every match is going to be right for you. eHarmony is about bringing two compatible people together who have a solid foundation from which a long-term relationship would have a high probability of success. You still need to carefully consider whether this particular person is one with whom you would like to further a relationship. If you feel the need to end communication, then be honest, direct and polite. The sooner you address this determination, the better for both of you. – eHarmony

S. was recently divorced and had two young children who lived out-of-state with their mother; it was evident very early on that S. missed them terribly (which was actually a very desirable trait in my eyes). What was also evident was that he just wasn’t ready to step past emails or text messages; when given my number S. would not, or more likely could not call me. He was otherwise charming, funny, and certainly a big enough geek that I was impressed; he just found an excuse not to call more than once, and I could feel his reluctance. I felt like I had a pretty good grasp on what was happening, so I put it out there that I would be just fine if we were just friends, a proposition he happily accepted. Since then we have texted a few times, I have emailed him installments as they have been published, and he has sent me screen shots of my eHarmony profile for posterity as they were not available for me to view. I would like to think that S. and I will be friends, as you can never have too many, and he is definitely the type of guy I enjoy knowing.

Never under any circumstances invite someone to your house or get into their car until you have known them for at least several dates. Nobody should ever pick you up at your house (or drop you off) until you’ve been out with them for several dates. – Wayne

If I had met M. for lunch in San Angelo, I fully intended to follow this advice. However, I did completely disregard that advice with someone I “met” through Yahoo.

You may encounter people outside of your geographic area. You should seriously consider whether you want to enter into a long distance dating arrangement. Until you’ve exhausted the pool of local daters, I’d advise you against long distance. You may also encounter people who claim to be traveling into your area on business – or will soon be moving to your state. I’ve always found it best to advise them to contact you when they’re permanently living in the area (the paranoid side of me says that these people are often already in a relationship and looking to setup some action outside their home town). Use extreme caution with people outside your geographic area. – Wayne

I realized fairly early on that all of the guys I was communicating with on eHarmony lived in the same Texas town, about three hours from mine. I rationalized that this was a good thing because it wasn’t too far to drive if we really liked each other, but it was far enough away that if we didn’t I would likely never have to see them again. In fact, I closed a couple of potential San Angelo matches because I thought I didn’t want to date anyone in my town.

Before you begin online dating, be sure you are ready for rejection. To get good at online dating you must accept that you’re going to be rejected quite a bit. You must build up a “thick skin” regarding rejection – and not take it personally. Every single person doing online dating gets rejected. It’s a normal part of the online process.

Recognize that a fairly regular portion of people you contact online may suddenly stop writing to you in the midst of what you felt was a pretty good email exchange. This is normal. It means they’ve changed their mind. Resist the urge to send a scathing email telling them how rude their actions are. Just move along to the next person. – Wayne

I confess, I closed on quite a few guys after guided communication started simply because I decided they were too short (I am 5″10″; call me shallow, but I don’t want to date a guy who is substantially shorter than me), had bad teeth (personal pet peeve, sorry), or who wrote cheesy replies. I’ll happily apologize right now for not wasting their time.

It is important to note that eHarmony does not perform background checks on its members. It is also important to note that our optional identity verification service, which is powered by our partner RelyID, is not a background check. We rely on the honesty of our members when filling out our eHarmony Relationship Questionnaire to supply us with their date of birth, marital status, city and state of residence, occupation, educational background and a myriad of additional items. Regardless of the connection you feel with any of your matches, we encourage you to do your own research before meeting in person. This can be anything from typing your match’s name into a search engine, contacting your state or local municipalities to obtain public information, or using a paid service to obtain a full background report. Above all else, use common sense. Pay attention to the details someone shares and if you find anything that doesn’t seem to add up, follow your intuition and close the communication. – eHarmony

Ooh, background checks! This brings me to a funny anecdote: When M. and I were in the email stages of open communication before I gave him my number, I ran him through With just his name and a general knowledge of his age, I was able to verify his birth date, his home address, that he held a professional license and was in good standing with the State of Texas, that he had never been divorced, was not still married, and had in fact never been married, and did not own property in the State of Texas. I also learned that he had a son listed as living with him who was old enough to drive, there were no females listed as living at his address (a pretty good sign that he was not living with someone); I also learned that he did not have a criminal history and was not a known sex offender. Using other easily available internet sources, M. was able to learn my home address, the fact that my mother is a registered Republican and donates to the party. I think we were both suitably impressed when we revealed our web-savvy to each other. 😉

And then there was Kevin, the guy I am now dating. As I mentioned earlier, I joined Yahoo Personals so that I could read the ads without getting a reminder to create a profile every time I clicked on someone. I also ran a search to see how many people it would match me with within a 250 mile radius. While it returned 129 matches of men who were looking for someone like me, it returned only one match who met my rather stringent list. He happened to live about 40 miles away, and I was already socially and professionally acquainted with him. Talk about a small world…

Birds of a feather can help build a relationship, but opposites won’t necessarily kill one! In the early stages of a relationship, having similar hobbies or interests, political views or intellectual pursuits, favorite sports or favorite actors will certainly provide something to facilitate bonding. However you couldn’t completely rule someone out based on one item, as that one item may very well prove to be trivial in the long run. Everything matches but you’re voting for McCain and she’s dancing like an Obama girl in her youtube videos – don’t let one thing sink the ship. That being said, very personal or deeply religious views may be the exception to the rule. – Jon

So here’s what happened. I did the search, saw Kevin’s name, went “Oh, I know that guy!“, and before I even read his profile I had shot him a Yahoo Personals communication saying “It’s pretty freaky to see someone I know on here; do you have any tips for the newbie?”

Be Honest in your profile! So maybe we’re not all 6’ 3’’ former NFL players with a passion for the arts and an advanced degree in microbiology from Oxford. And just because it’s the internet doesn’t make it alright to pretend to be one! Not to mention that it is now easier than EVER to find out if someone is lying. Quick searches of public databases will reveal a person’s true age, and their facebook or myspace probably has a link to one or two close friends who have posted actual photos of the person somewhere. Lying in a profile can not only bomb the chance you had with someone, it also sets up an implicit understanding within yourself to be distrustful of other people’s profiles. And if you think everyone else is lying (er, I mean “Self-enhancing”), then how can you ever find someone truly compatible? – Jon

Then I went back and read his profile and immediately wished I hadn’t been so flippant. I read his profile once, twice, three times…okay, I admit that it was more like ten times, and really wished I could yank that email back from cyberspace and word it a little bit more carefully.

I needn’t have worried.

Kevin wrote me back and suggested dinner at one of the few nicer restaurants in San Angelo; I almost fell over. Do you know how rare it is to get asked to dinner anymore? It’s always, “would you like to go for coffee?”, which to me implies that the guy either isn’t confident enough in his own social skills to make small talk through an hour of lunch, or he is so unsure of my social skills that he thinks I couldn’t. Either way, I think it is slightly insulting, and I always turn down “coffee” offers; but that’s just me.

Dinner, on the other hand, implies a slightly higher level of interest: it means that the guy thinks you have enough in common that you could comfortably get through what might turn into a two-hour meal, depending upon the restaurant chosen. I was intrigued, even if I was probably over-thinking everything (as I am known to do). 😉

Where do you go on a first meet?

Notice I used the word “meet” — because that’s all it is. The first get together is an opportunity for you both to get to know each other. It’s not a date and you should always arrange for it to be in a public place. The best spots for these are coffee shops because you can meet for 15 minutes and be on your way. Avoid the temptation to meet for dinner. If the initial meeting doesn’t go well – you’ll be stuck for an entire dinner making small talk. Even though brief coffee dates seem boring and cliche – there is one reason that people use them — they work.

For someone who hasn’t online dated before – you may wonder what the protocol is at the end of the meeting. Do people kiss, shake hands, bow? I’ve never ended a first meet by trying to kiss someone and have only sporadically heard of it happening to others (usually with negative results). Typically the first meet ends with a handshake. If it went well, guys will very often set up the next date opportunity during this time. – Wayne

I wrote Kevin back and mentioned that I was driving to Fredericksburg the next day to take photographs; I asked if he would like to meet me there. Realizing that this required a certain time and gas commitment for him (F’burg is three hours from me, and only slightly less from him), I almost immediately yanked the offer back, saying I didn’t expect him to drive two hours just to have lunch with me.

He wrote back and said that Fredericksburg sounded like fun, and he would like to go with me.

I almost freaked out. I mean, sure – this was a guy that I had gone to school with (6 months in the 7th grade before he moved out of state), and we knew each other socially and professionally, heck we had even met each other’s ex-spouses, but were we ready for a two-hour drive each way as well as a day spent together? When he called me later that afternoon, I asked if he would mind driving to San Angelo to see me before the next day, and he readily agreed. He came to my house, we spent a few hours talking and getting to know each other, and then he left. We were on for the next day, and I had broken another of everyone’s rules.

Definitely plan a first meeting in a public place, but don’t necessarily bring along the friends! The advice we give our teenagers still applies to adults, even into the golden years. First of all, no normal person will balk at the suggestion you meet for the first time in public (ever hear “Then she asked if we could have dinner?!?! I just figured we’d meet in my car and drive to my place!” from someone you’d want to date?). Second, public places give many opportunities to get to know the person in ways you probably wouldn’t be able to do alone. Is She drooling over you yet also flirting with the cute waiter? Is he throwing every compliment in the book your way yet treating the hostess like garbage? These are clues that will no doubt help you understand more than any internet profile or chat ever can. And as far as friends go – save them for later – they’ll be intimidating on the first date. – Jon

An hour or so later, I sent Kevin a text message asking if he had made it home safely. He replied that he had.

My advice to women is that if you had a good time on the initial meeting — you send ONE short thank you email indicating that you are open to another date. Then the ball is squarely in the guy’s lap and the woman does not communicate again until the guy asks her on a date. (Note: This is one area that the sexes seem to disagree  – with many women feeling the ball is squarely in the guys court and there is no need for a thank you after the initial meeting. I found that with online dating since all initial contact is via online – that both parties should feel comfortable using online contact to indicate whether they want to go out again). – Wayne

The next day, I picked Kevin up and we had an enjoyable ride to F’burg. We spent the day there, I took pictures, we ate together, hit some of the little shops, and then I drove him home. When we got there, he offered to cook me dinner; this was without him having read my eHarmony profile about how I like a guy who can cook, mind you. All in all, we had what had to be just about the best first date ever; I’d like to think so, anyway.


Kev’s and my first date in F’berg. June 8, 2008

The next day, Kevin sent me a massive bouquet of roses; he also removed his profile from all of the online dating sites … not that I don’t still tease him about them. 😉

I should back up for just a moment here: Kevin was also on eHarmony, and the only reason we think we weren’t matched by them is because we had both marked ourselves as unwilling to relocate, even though he actually lives in one of the only places I would ever consider relocating to (he lives in the county which holds my family’s ranch). Small world, indeed.

According to eHarmony:

Meeting in person is a very exciting time. Most of all you just want to have fun and explore the level of chemistry that you share with your date, but don’t let high hopes cloud your ability to exercise reasonable caution.


-Choose the time and place of your date wisely. Meet in a public place at a decent hour during which lots of people will be around. Lunch dates work especially well.
-Limit alcohol consumption or abstain entirely until you know the person better.
-Use your own transportation, even when meeting someone who lives a great distance away from you. It’s never a good idea to get into someone’s personal vehicle on a first date. Wherever possible, drive yourself, or take a taxi.
-Tell at least one friend or family member about your plans, and arrange to “check-in” with them after each of the first few dates. -Carry a fully charged cell phone with easily accessible emergency numbers.


-Leave beverages or personal belongings, such as purses, wallets, jackets with pockets, that may contains items that could reveal personal information about you, such as a driver’s license, credit cards, ATM receipts, etc.
-Do not meet at your house or place of work, or give that information out until you have had a good opportunity to know the other person better.
-Go home with someone, even if it feels like everything’s going great. You have not spent enough time with them enough to assess whether your safety is at risk.

Yep; I broke many of the rules…

While online communication can accelerate one’s sense of comfort and intimacy, we can’t stress enough how important it is for you to take your time getting to know your match. We encourage you to use eHarmony’s anonymous Open Communication system as long as necessary to find out as much about your match as is reasonably possible.

Even though eHarmony’s matching process creates extremely compatible matches, compatibility alone does not eliminate the need for real-life experience. It is vital to date and get to know each other in a deep, revealing and meaningful way by sharing a broad base of experiences together. The more experiences you share, the better your chances of avoiding hidden and sometimes unpleasant surprises. So allow time for a variety of experiences together, particularly the simple everyday routine. In cases of long-distance relationships, if possible, you should consider living in the same area for a significant time before committing to a more serious relationship. Move slowly, learn about and pay attention to the reality of your new relationship, as well as your relationship goals. – eHarmony

This is a really good point that I have been meaning to talk about. Reading someone’s online profile, assuming that they have filled it out truthfully and completely, really can give you an artificial sense of knowing someone. Much of the information given is stuff that it can take weeks, sometimes months to observe and learn about someone, yet you go into the relationship already knowing it. It’s like knowing someone’s bottom line in a way, but having no idea why they are that way, or how they got there, so you are learning about them in a way that seems a little bit backward and unnatural from the typical non-online dating relationship. I’m not going to say whether I think it’s better or worse, it’s just different.

Note For Guys Doing Online Dating: I developed a rule of thumb that I would always end the first actual DATE with a kiss. If she wasn’t interested — you could tell right away. Better to know up front then to be strung along for another several (expensive) dates. This portion of the date is difficult for most people to fake unless they feel some attraction. If there was a better way to gauge someone’s interest, I never found it.

Once you’ve met – the hard part begins. Determining whether both people want to go on a date.

As a guy I’d never follow-up with a request for a date unless the person i’d met sent a thank you or responded with enthusiasm to my thank you email  for the initial meeting. I’m sure that I guessed wrong more than a few times. My experience is that if people want to go out again – they aren’t shy about letting you know. And the opposite seems true – if they don’t want to go out again – they’ll be very quiet and not follow-up with you after that first meeting. – Wayne

Reading “the rules” now and imagining following them in Kevin’s and my situation just seems so stilted and unnatural, but I am sure if I hadn’t already been so well acquainted with him before, I would have been much less likely to be so trusting. Obviously, you must listen to your gut every step of the way, and do your best not to step outside of your comfort zone or do anything stupid.

Here are some others’ experiences about what did or didn’t work…

I remember  one of the things that caught my attention about June was her answers to the q&a part of the process, she actually answered my questions with full thoughts and opinions. It left the impression she wanted to try and find what she was looking for. Once we started talking on the phone and I knew I was really interested as was she, I knew the next step was meeting face to face and us spending time together to see if it was what I thought it was. The kicker was she lived in Northeast Canada and I lived in Southwest Texas. – Steven, 32 [eHarmony]

Okay, so here is someone else saying that your responses matter. You should reply in a complete and coherent manner if you want to impress someone who is halfway literate.

Be prepared to “meet” people on IRC who live far away, as in our case – it was 10,000 kms (which is some 6,200 miles. – Wolfgang, 51 [IRC]

If one of you possesses a willingness to relocate, it can definitely help your chances to find a good match and broaden your dating pool.

I found that women with an attractive picture get tons of responses, most of which are from completely unsuitable men. I felt rude not responding but found it too emotionally draining to try to be kind to all of them after a while. My impression is that there are a LOT more men than women on these sites. – Jennifer, 44 [Yahoo,, eHarmony]

I totally agree with Jennifer on this one; there is too much work involved in being kind to everyone who reaches out when you just aren’t feeling it. You have to remember that this is the one time when it is okay to be selfish and close communication. Unless you are only communicating with people in your town, and your town is really small, then the chances are very good that you will never see this person in real life. Close it down; move on.

Okay, so I’ve shared Wayne and Jon’s rules, and you have read eHarmony’s suggestions; now it is time for me to give you some of my Do’s and Don’ts; feel free to take each with a grain of salt, your mileage may vary, and all the other usual disclaimers.

1. Listen to your gut: If something seems wrong, it probably is. If someone rubs you the wrong way or does things that make you uncomfortable, then you should follow your inner voice and ditch them. Fast.
2. Be open to the experience: Be willing to step outside your comfort zone a little bit for someone who intrigues you, but not in a way that compromises your own personal values.
3. Be picky! Create a list of must-haves and deal-breakers, and don’t compromise on them. This is the one time in your life that you have the opportunity to pick or reject a suitor based on what you want. You are worth it, and yes – you deserve it.
4. Be honest: If you don’t want kids, say so; hate pets, say so; have a strong religious preference, say so. Whatever you do, don’t embellish and don’t sugar coat your past or current anything. If you scare off a potential match because of your honesty (assuming he or she is looking for the truth), then it is better to find out in the earliest days … then you can move on.
5. Be Patient: A good match can happen quickly, or it can take months – sometimes even years.

1. Settle: If someone consistently does things that upset you, raises your personal red flags, or makes you uncomfortable in any way, then move on. It is better to be lonely by yourself than to be lonely with someone who is unsuitable for you.
2. Feel guilty if you are talking to more than one person at a time in the early days; this was hard for me, but I got over it.
3. Be afraid to take chances: if you don’t try, then you won’t ever know if there is someone out there that might be your someone special.
4. Be afraid to say what you want: There is someone out there who is compatible with you, online dating may be a possible way to find them.
5. Let online dating consume you: It can take a lot of time to manage online connections, you should still make time for possible real life ones. Get out there, do things that interest you, and don’t stop looking until you have found what you are looking for.

Perhaps my most important suggestion is that no one should ever do this on their own. You should always have a friend (or even better – a group of friends) that you can bounce your profile off of, who will listen when you talk about potential matches, critique your photographs, and who you will trust when they offer helpful comments or criticism. Throughout this whole process, I have relied upon Wayne, Clinton, and Dan for their friendship, advice, and constructive criticism. My hope is that anyone else who even considers online dating will have at least one friend who will be there for them as these guys were for me.

Next time we’ll cover the experience from others’ perspectives…

Next in this series: Online Dating: The Experience

Previously in this series: Online Dating: Choosing a Site and Online Dating: Writing Your Profile

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About the Author

Judie Lipsett Stanford
Judie is the co-owner and Editor-in-Chief of Gear Diary, which she founded in September 2006. She started in 1999 writing software reviews at the now-defunct; from mid-2000 through 2006, she wrote hardware reviews for and co-edited at The Gadgeteer. A recipient of the Sigma Kappa Colby Award for Technology, Judie is best known for her device-agnostic approach, deep-dive reviews, and enjoyment of exploring the latest tech, gadgets, and gear.

12 Comments on "The Do’s and Don’ts of Online Dating"

  1. Judie – I may have glanced over this but how many people did you meet face to face during this online dating experience?

    You have a lot of “well I ignored the conventional online dating wisdom and it didn’t affect my search” yet I’m not sure how well ignoring conventional wisdom would have worked if you’d met 5 – 10 or 20 people (not uncommon at all for online) – especially given that it seems like a 3 hour drive to get to a nearby city/suburb in your area is not uncommon.

    Believe me if you were to get into the active online dating mode where you have first meets with lots of people – I think you’d be much more into coffee meets than dinner out. There are a lot of problems with these lengthy dinner first meets – not the least of which they are both time consuming and expensive for a meeting which statistically usually doesn’t work out.

    Anyone who ventures into the online dating world should think about reading about the actual experiences of others before starting up their own adventure.

    A good resource is iVillage:

    Plenty of Fish is also free and has a very active message board – though I don’t think they’re as serious an online dating service (it’s free so you’ll probably find a lot of casual lookers there)

  2. Wayne, I totally agree that my experience wasn’t usual and if I had dated a lot of people I had met online I would have likely changed my tune. I didn’t have to, thankfully. 🙂

    And since I know that every experience is different, and mine is certainly not the norm, that’s why the next installment will mainly be a lot of gathered experiences from our readers. 😉

  3. spmwinkel | July 1, 2008 at 10:51 am |

    Just wanted to say how much I like this series of posts. It’s not gadget-related etc. but it’s still very interesting to read about this part of the internet. In the Netherlands there aren’t a lot of places that can’t be reached with 3 hours driving so taking that into account distance shouldn’t be a vert big problem, but I guess living in a small country means that we have some other demands (2 hours drive or something like that). Also, I think we’ve got less dating sites. But I’m totally not basing that on everything because I only chatted for a while on a free site that wasn’t focussed on dating, so that doesn’t count. (I did meet some ‘possible matches’ there but it never really got rolling)
    Anyway, a small country with less people means that there’s less market for many dating sites.

    But the tips given here are useful for everyone around the world, and the personal experiences added to that make it all a lot more lively, which makes it so much more interesting.

    So do Kevins blue eyes by the way, they’re so blue!

    P.S. Twitter is down again. I know it’s off-topic, I normally wouldn’t post it here, but hey – I can’t post it on Twitter so I have to go somewhere.

  4. Urgh…Twitter! I haven’t done have the updates I would like to because they are constantly down! 😛

  5. If anyone is reading this and doing online dating but not getting the results that they want — I would be happy to review your profile and give you feedback.

    I did the whole online thing about about a year – and learned a lot about what works for profiles.

    You can email me directly through the site.

    I just need your profile name and the site you’re on (eHarmony is not viewable so I can’t offer much advice there).

    I’d love to do it as an article but realize not everyone is into sharing — so this would all be one email analysis with suggestions.

    email – [email protected]

  6. Let me be one of the first to HIGHLY recommend Wayne’s profile critiquing services. :mrgreen:

  7. TrvlngDrew | July 1, 2008 at 10:03 pm |

    He he.. I have to agree with you Wayne.. Coffee stuff is very important as it can be 15 minutes or an hour.. And yes as you say, you have to meet EASILY 15 people to find someone you connect with. It is exhausting.. Not to mention all the emails and other to get to the 15!

    I’ll be sure to use Wayne as a sounding board, if I ever bother to venture back into the on-line dating world.. More inclined to give up these days 🙂

    As for the kiss, it is critical in Europe and Australia as it is a common greeting between women and men that have any sort of relationship including business.. Obviously there is a comfortability and aquaintance perspective but very uncommon not to do a cheek kiss.. If it is the first time then it signals the intent of the male’s relationship in that female’s life. Also very critical.. If the female doesn’t like it, its obvious and time to move on..

    Air kisses don’t happen.. Seemingly insulting..

    Was talking to the GF last night and she mentioned she knew someone that was on RSVP.COM.AU and had already been scammed by a Nigerian for $2k and still hadn’t figured it out.. Was still in contact!! 🙁

  8. Most of the meetings don’t go horribly. It’s just a matter of finding the people that you feel like you match with. I’ve been guilty of jumping right to dinner on the first meet and after a few of those I was left wondering why I was paying all the money and sitting through two hours of polite conversation when I could have accomplished the same objective (initial meeting) in 1/4 the time.

    The more you do the more you start to get the hang of how to manage these meets efficiently.

    It sounds rather cold but in the end online dating is a big numbers game imho.

  9. AndySocial | July 2, 2008 at 11:11 am |

    Congratulations, Judie. Now I can tell my fiancee I won’t be leaving her for the geek lady down the road. 🙂

    Kat & I also met online, via Match. She lived in Lubbock at the time, and after her driving down here for meetings for a few months, she moved down here. We broke most of the rules, too, I think. But, over a year now and still no problems at all – can’t beat that.

  10. What a wonderful read. I was looking forward to this and had told my wife about it so she could read it as well. We’re very happily married, but it is very interesting to see how much things have changed (yet not) in the past well over 20 years since I last had to ask someone on a date.

    It is interesting reading about evaluating by contrasting behavior towards you with behavior towards others, because that is something I teach my kids and do myself on a regular basis – you learn a lot by seeing how people behave towards those they don’t need to be nice to!

    Really great article – and I’m very happy you’ve had success. I’m a sucker for happy endings 🙂

  11. I have re-subscribed to Gear Diary’s RSS feed. I never got ANY of the posts in this series!

  12. Not acceptable! 😉

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