A successful guy’s online-dating guide, Part II

by GK on March 25, 2012 · 11 comments

As promised, here’s Part II of Gal’s online-dating primer. Part I is here.

Third, Who Are You?

For a guy, the Internet is no different from a club. It will still be up to you to make the first move and you will still need to impress your target.  With online dating you have three tools: the picture, the message and the profile.

  • Picture: Looks matter, even online.  This is the first thing a girl will look at when she gets your message, so get a picture that makes you look good.  Do NOT post idiotic pictures of you looking like a douchebag. Do not post pictures of your genitals (yes, some guys do this).  Do post pictures of yourself doing something interesting.  OKCupid did an amazing study of online dating pictures which you should really read: http://blog.okcupid.com/index.php/the-4-big-myths-of-profile-pictures/.  My most popular pic was of me running through the snow with my dog.  Second popular was hiking. Neither showed my six-pack abs.

    online dating profile

    Tell her about the real "Hunger Games."

  • Message: Authenticity counts.  After checking out your picture, the girl will check out the message you sent her. Remember, these girls are getting dozens and sometimes hundreds of messages a day, so you need to stand out. Don’t just send a picture that says “hello” or a “wink.” Spend some time and show her you actually read her profile and didn’t just check out her cleavage. Pick out something from her profile that you have in common and comment on it.  Compliment her smile in that picture of her with her puppy and take the time to say something about yourself in this message that isn’t in your profile.  When I sent out messages, I would always be upfront and tell the recipient why I sent her a message. For example: “I noticed that you loved ‘Firefly,’ that’s my favorite show! I’m still waiting for the second season…” or “Love your smile in that pic of you hiking. Is that Yosemite?”  And yes, always ask questions. You want to give them a reason to respond back and not just forget about your message.
  • Profile: If your pic and message are good, she’ll now be checking out your profile. Again, be honest and have a sense of humor. Don’t go for cheesy stuff like “love to travel and enjoy long walks on the beach.” Girls can spot bullshit like that a mile away. Tell them what you’re really like, be funny, say something unique and don’t be afraid to share something a bit embarrassing (On my profile, I stated that I had a horrible taste in movies and mentioned that I just saw “Mega Shark vs. Giant Octopus.” You’d be amazed how well that works).

Fourth, Take It Slow but Go For The Close

Don’t rush things. Exchange a few e-mails first before taking it offline but do move it offline sooner rather than later. If you’ve been writing e-mails back and forth for the last four weeks, you’re building this up to be something more than it is and you’re going to be disappointed. My usual rule is three messages. If she’s not meeting me after the third message, I’m polite but I move on.

A few tips

  • On your second exchange of messages, ask if you can send a message to her personal e-mail instead of her dating site inbox.  If she’s not willing to do that, she’ll never actually go out with you.
  • If she responds and tells you to check out her hot pictures on her personal site, don’t do it.  To quote Admiral Ackbar, IT’S A TRAP!!!  (I’m assuming most people aren’t this dumb but it still needs to be said).
  • Don’t suggest something high pressure. A fancy dinner on the first date is bad. Suggest something public and low pressure like coffee. I met my wife for our first date at the farmer’s market, by the way.

Finally, Set Your Expectations Correctly

You’re a guy on a website full of guys trying to land a date. The average response rate I got was around 20% and that’s considered really good. It’s just like a bar where sometimes you’ll strike out and sometimes you’ll hit a home run. Just enjoy yourself and the experience.


1 GK March 25, 2012 at 11:54 pm

Thanks again, Gal. One funny thing I learned last year: Although you are better off tailoring the initial e-mail to the woman’s profile, you can get away with a more generic message if your pics and profile are solid.

My friend showed me a ridiculously brief, canned e-mail he was using with girls on OK Cupid, and he was setting up lots of dates with it. I tried it on Match, and although my response rate was worse, to my surprise it wasn’t by much. Saved me a lot of time, too.

However, I would suspect that on a more relationship-oriented site like eHarmony, this might not work so well.

2 Boss March 26, 2012 at 8:01 am

Excellent post! It’s amazing how we have almost the same pointers on this type of thing. A few things I’d like to add:

1. I usually request a girl facebook me after a message or two. This does a few things besides just move you to a better messaging medium: A) They can see that I’m a real person, I have friends, people are writing on my wall about the stuff I’m doing, etc etc. With the 22-27 crowd, seeing your FB profile is much more real than your OKC profile. B) You can now see her pics. With about 50% of the girls, I realized the few pics they posted were very flattering of them (I ditched the date)… and on one, the exact opposite (way, way hotter!!!).

2. Really let the online dating thing work for you on the first date. Without exception, I was always able to build fantastic rapport with the girls in the first 20 minutes over awkward/terrible previous dates. Makes a very easy opening into talking about each other personally and move into GK’s Big Four.

Have fun folks :)

3 Boss March 26, 2012 at 8:10 am

Guess I’ll add another item specific to the 22-27ish crowd. Although online dating isn’t taboo anymore, the girls I’ve met have always stated that they have turned to it because they were unhappy with the guys they were meeting. That’s fine if you consider what role they’re trying to fill with finding a guy (you).

GK wrote an excellent article on women and age. Do read if you haven’t…


I agree with what he wrote although I’ve met a few girls who have had their shit together at age 24-25. 23 and under is sketchy: If she’s really that hot and social but she’s looking for a guy online, she’s probably got issues. Sorry. All I’m saying is that if you’re looking for a relationship and not just to be somebody’s hookup, stick to the 24 (preferably 25) and up.

4 SW March 26, 2012 at 8:12 am

Great observations, thanks Gal!

I’ve had similar experiences as Boss, and I’d like to offer the other obvious form of communication after the three exchanged messages (yes I like to have a few messages first too, just to get comfortable with the girl and allow her to feel comfortable with me too), and that’s the cell phone number.

Might seem a little bold, but this day and age in the 20somethings crowd a text message goes a long way. It allows you to communicate in a more convenient manner since most people always have their phone with them. I like to do this personally, and I’ve found that once I offer my number in the second or third online message, the girl will 9 times out of ten give me hers in the next message, with a followup like “looking forward to talking to you.”

Again, great tips all around, thanks all

5 Gal @ Diamonds or Dogs March 26, 2012 at 9:31 am

Yep, as in life so goes the internet. You don’t need to be perfect and if you have a good profile and a good pic, you may not need a great message. It’s all an issue of how much time you’re willing to spend. Your friend could have probably gotten an even better response rate with a less generic message but that takes a lot of time. So if he’s doing well, why mess with that?

Facebook is tricky. Some people don’t like letting you into their private life so quickly. I think it took my wife 6 months to friend me :)

And in regards to your comments about age, I’d say that’s true online and off. Under 25, most people aren’t really serious about relationships, and that applies to both men and women.

I actually found texting to be the best next step to messaging through the dating site. It’s more personal than email but not too personal. You can flirt a bit too, while setting up your date .

6 GK March 26, 2012 at 7:06 pm

Thanks for the comments, guys!

Boss, your Facebook strategy is an interesting one. I usually avoid friending girls I’m dating so I don’t have to deal with UN-friending them later. But I can see how it’s effective with younger girls. Have you managed to avoid much awkwardness with it?

7 Julie March 26, 2012 at 7:40 pm

Re: Texting: As a woman who’s dated online and since married from that pool (the guy above :), I’d say keep the pre-first date texting focused on setting up a date. Since flirting is so easy over text, a lot of my pre-first date texting seemed to set up a false sense of intimacy that didn’t fit with the slightly awkward first date; I in turn, correctly or not, put those guys in the “lack of in person chemistry” bucket. I have many friends who’ve texted with guys for weeks and never progressed to the actual date. Good Luck!

8 SW April 2, 2012 at 3:26 pm

Absolutely agree with Julie in regards to having too-intimate texting pre-first date, and how it can set up for failure to cause you to put them (or them put you) in the “lack of in person chemistry.” I’ve actually just had this happen, so I too learn from my own mistakes. Texting in general is a great tool to use though for getting each other to not be so on guard with someone they just met; it can allow you to be more personal… when done correctly :)

9 Boss April 5, 2012 at 7:54 am


I’m not scared of de/unfriending. When you cut things off you cut things off, a click of a button doesn’t make that any more or less awkward. However, as I stated above, you have a lot to gain from adding the girl on FB. When there’s 500+ photos of you vs 4, it reinforces the fact that you do, in fact, look the way you claim in your OKC (or whatever site) pics, and and you really are who you claim you are. In turn, you can see if the same thing is true for the girl you’re about to go on a date with.

The only downside is that if you’re dating multiple girls you could start to see numerous posts from girls appearing on your wall which are flirty and could cause some clash. Solution? Yep, I got you covered:

FB Privacy settings are a funny thing. If you take a moment to adjust them, you can set it up so that only you can post on your wall, or that posts from other people can be only seen by you, etc etc. It’s not that hard to keep things on the DL!

PS I didn’t defriend you, I just took a hiatus from fb 😉

10 GK April 5, 2012 at 5:14 pm

Thanks for the explanation, Boss! I just might try your idea. And I’m glad to know I’m still in your good graces. :)

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