Dating, Internet Style

Online dating. Those 2 words can provoke intense reactions from the women in my life! Everything from fear (the ones who’ve never tried meeting random strangers online) to disgust (the ones who’ve been there, done that, and given up) to embarrassment (the ones who met their mate there) can be expected. I sympathize.

Two things happened recently to make me revisit my own gone but not forgotten days of scrolling for dudes on the interweb: a couple of my friends have asked for my guidance as they dive in and give it a try, and I attended the wedding of a friend who met her terrific husband online.

Adrian Tomine Illustrates Online Dating for The New Yorker

Adrian Tomine Illustrates Online Dating for The New Yorker

Full disclosure: I did not meet my beau on an internet dating site. But I did go on about a zillion dates, more or less, with people I met online. And a handful of those guys were actually pretty awesome (the rest were mostly boring and I left after the requisite 1.25 hours). The one thing that was consistent was that I usually got fairly decent responses to my profile and only seldom received the annoying “msg me u r hot” type messages.

So I’m going to give you the same advice I gave my friends because I know how hard it is to stare at the empty web form and try to come up with something. But first-

Why should you, or anyone, try internet dating?

Pros: Unless you belong to some closely knit group where there are many eligible people who share your values, like a cult, a political organization, or a sports team, it’s difficult to meet hot singles to go on dates with. This is especially true after your mid-30s because any party you attend is guaranteed to be packed full of COUPLES. Trust me, I know what it’s like to chat up the hot Spaniard only to be introduced to his wife. There may be one divorced guy at the party with lots of emotional baggage… if you’re lucky.

This is what makes online dating awesome — If you live in a largish city, there are tons of people you might like that you never ever see. Online dating magically uncovers those hotties that walk their dog in different parks than you do. And, if you’re in a small place, then you get to broaden your horizons from the comfort of your own living room. I’ve always said that it doesn’t hurt to keep all your options for meeting folks open by maintaining an active profile.

Cons: Remember how I said that I didn’t meet my current [and hopefully forever] love on the web? Yeah, the top place to meet your future mate is at work (or school, if you’re younger). This is the kind of statistic that made me groan as a single librarian given that the overwhelming majority of my colleagues are female. Even so, I met my guy in the vicinity of my job where he also worked. I just had a feeling about him even though he was completely unlike any of my friends or previous dates.

And that’s the problem with the online; it’s just a list of attributes. This isn’t like picking out a new laptop, it’s about LOVE. There’s a certain intangible quality to compatibility, whether we like it or not. But, because it’s difficult to quantify things like “openness” or “warmth”, we try to weed out the incompatibles based on their habits or education level. In High Fidelity, the main character says that it’s not what you are like, but what you like that matters. The truth is, what you like might be an indication of what you are like in some cases (another friend connected with her man online based on a shared appreciation for a specific author), but not always. And in my case, not at all. So buyer beware, you might as well just go for the ones whose photos you like; it’s not a science, it’s animal instinct.

John Cusack as Rob in High Fidelity (2000). Read the Nick Hornby book, it's much better

“Book, records, films — These things matter. Call me shallow. It’s the fucking truth.”
John Cusack as Rob in High Fidelity (2000). Read the Nick Hornby book, it’s much better

That said, here’s how one should go about being a skilled online dater

1) Chill, enjoy the experience: This goes for all dating, in fact. I’ve sometimes felt I was being interviewed for a job while on dates. Hey yo, the odds are you’re not meant to be together forever. But it’s still fun to meet new people. Try not to be goal-oriented, just aim for interesting conversation and a nice time. Where you see yourself in 5 years need not be discussed on a first date.

2) Pictures: You should post at least 2 photos — one of your face, and one full body shot that reflect how you actually look now. Yes, it should be the cutest version of you, but not the version that existed 10 years and 30 lbs ago. Here’s my thinking, you want people to like you for you so, if you’re a bald man don’t be wearing hats in all your photos, and if you’re obese then you want to meet people who find you attractive AS YOU ARE NOW.

3) Don’t waste anybody’s time: This is related to no.2. For example, I don’t like scrawny guys. I’ve been on dates with the cool skinny dudes, but really I was just wasting everyone’s time because only physically strong men turn me on. You must decide what is fundamentally important to you (see 3 Things = Love). If you’re a hunter, you may fall in love with a vegetarian, but only if hunting is an occasional pastime rather than an integral part of your identity as a human on this planet. Know your deal-breakers.


You looked hotter online

4) Be specific: This is the MOST IMPORTANT piece of advice I have for anyone writing a dating profile. Let’s agree that you can’t explain who you really are in a short dating profile. First off, you don’t want strangers to know too much about you; there should be substance there, but it shouldn’t be longwinded. What you can do is give the people reading it something to grab on to! Sure, you like listening to music, going out, but also staying in, and you’re a hockey fan… Are we having fun yet?

Instead, try writing about the best live show you’ve ever attended. How about what you enjoy doing on a Sunday morning? What makes you special? I have a friend who is great at casting actors in the imaginary film version of the book she just read. That’s the kind of unique quirky (yet benign) thing I would suggest putting in a profile. You’re not bland and neither should your profile be.

4) Don’t be too sexy: You like sex, I like sex. And, if we’re being honest, if it wasn’t for sex none of us would be doing this. However, you can’t put your sexiness out there unless you’re just out for hookups. Why? Because, once men see sexy they have a hard time seeing anything else. Keep the suggestive comments and pictures to yourself for now. For instance, I excluded my profession from my profile because, otherwise, I just got a lot of “sexy librarian” comments. Yes, it really is that bad out there in cyberland! Save the sexy for real life.

5) Block creeps: A picture speaks a thousand slimy words. Any guy posing without a shirt on is looking mainly for sex; use that information as you see fit. And beware the sad loner with the webcam self-portrait taken in what looks to be a basement apartment, yikes. Most of all, anyone with a long list of what they don’t want must be blocked. Example: you cannot have any baggage, play games, or have children, and you cannot be too into yourself… yeah, anger issues.

This is what I'm talking about

This is what I’m talking about

6) Keep it real, keep it short: First, turn off that instant messaging feature immediately! Now, congratulations, you’ve decided to email someone. Hopefully they’ve followed rule no.4 and you’ll have something to run with. So write something true and simple, like “Hey, I enjoyed reading your profile. The part about how you can’t cook to save your life and once burned a pot trying to boil an egg made me smile. I was pretty clueless too until I spent a summer with my aunt in Austria and she taught me how to make cakes and sausages. I’d love to go back to Europe some time. Have you traveled much?”

Boom, that’s it. Keep it short, but include a question so they have something to respond to. You can make jokes but stay away from LOLs and too many smiley faces; you’re a grown-up, write like one.

7) Meet soon: The longer you communicate with someone, the more you get an idea in your head about who they are. And that idea is wrong! As soon as you establish that a potential date is engaging and not a serial killer, try and hint at meeting for coffee soon. Someone who doesn’t want to rendez-vous is hiding something. You’re there to meet people, not to find pen pals.

A note on safety: obviously meet somewhere public, early evening, and don’t give out your address or personal email. Also, don’t accept lifts. I think exchanging mobile numbers is ok, but only if you’re comfortable with it. 

8) Don’t take it personally: You thought he seemed great, but he never responded to your message. You had a fun email exchange, but she ignored your last one. You went on 2 dates and then total silence. Hey, it’s not you! Really. You never know what’s going on in someone’s life, but chances are it has nothing to do with you. Or… maybe it is you and they didn’t follow rule no.3. They communicated with you even though they hated your hair/face/body. Fine. Now it’s time for you to move on. As my good friend would say “Suivant! Next!”.

Have you tried dating sites? Is it a good idea — what advice would you like to add?


  1. Solid advice… And I am feeling hopeful that maybe I can also meet a real live human male despite working in female rich environment… And yes, online weirdos with the “hey ur hot” comments deserve a smack in the back of the head!!

  2. Never got to try it, so it is interesting to read about it! I did my dating the old fashioned way—met in the ONE class that we both took in University and then that was it! Of course, he is the only person I have ever really gone out with and now he is my husband, so it worked out 🙂

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