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When Should You Have Sex when Online Dating? The Rules Have Changed

Updated on July 13, 2011

When Should You Sleep With Him? How Online Dating Changed The Rules

A reader of my online advice column Dear Annabelle recently asked me when should you have sex with a guy you met through online dating. Normally when someone asks me how long to wait before having sex, I say 3 dates is a perfectly respectable time. Sex early in a relationship is good because it creates a connection in the beginning that you can build your relationship upon. However, this only applies to the "old-fashioned" way of meeting a guy and online dating is a completely different ballgame. So the question becomes...


How Long Should You Wait to Have Sex with a Guy You Meet Online?

You're going to Meet 3 different types of men online dating.

The Guy who thinks there is something better on the horizon.

The Guy who is there for lust instead of love and

The Guy looking for Love.

Your job is to figure out which one you're going out with and decide when to have sex with them. I'm going to address all three types.


1. The Guy Who Thinks There Is Something Better On The Horizon:

In my article 15 Things a Man Must Do When Online Dating, I caution men against believing there is something better looming on the horizon. Online Dating creates the attitude that there will be a better match waiting for you on the computer when you get home from your date. When you meet organically, you aren't distracted by thousands of other girls waiting at home for you. Online dating makes #1 too picky and unrealistic.

In #1's mind, there are a million girls online waiting for him. He becomes overly critical and instead of accepting (and even coming to love) what he perceives as a flaw, he say eff it and moves on to the next girl because she might be perfect.

When Should You Have Sex With Guy #1?

Realistically Guy #1 has boyfriend potential. He's there for the right reasons but distracted by too many woman and his inflated ego. That being said, I'd wait until you have the monogamy talk. If the two of you are boyfriend / girlfriend, there won't be any "perfect girls" waiting for him online because you'll both be shutting down your profiles for one another.


2. The Guy Who is Online Dating for Sex:

As much as we want to deny it, these guy exist. For whatever reason, they don’t want to settle down and they don’t want to put in the time to find someone to casually have sex with. Online dating has given these pigs millions of girls desperate to find love. We’re easy prey to them and we don’t stand a chance. Or do we? The good thing about these dogs is that they are wolves in sheep’s clothing that are really easy to spot.

When Should You Sleep With Guy #2?

Unless you’re on for sex – Never. So how do you spot the wolf? There’s a few ways. If you suspect it, just ask him. If he’s a wolf, you’ll surprise the hell out him and make him squirm.

Another way is that they aren’t going to put in much time. They’ll probably skip over the email wooing process and ask you out within 2 to 3 emails. Another sign is they will probably ask you out for drinks instead of dinner and undoubtably try to get you into bed on date one.

So how can you be sure if you’re dating a Wolf? Easy. Don’t sleep with him. If this guy is in it for sex, he’s going to lose interest fast. Remember he has a million other desperate girls to pick from who will sleep with him by the second date. #2 won’t stick around long enough for you to sleep with him, unless you make the mistake of doing it before he gets bored.


3. The Guy Who Is Looking For Love:

This is the guy you want to meet while online dating and I’ve been to enough Weddings to know they do exist. He’s there for the right reasons and if the two of you have a real connection, the rules of dating go back to the way they were before the advent of online dating.

When Should You Have Sex With Guy #3:

This is the trickiest one of all because when you meet this guy it’s going to feel like you met the “old-fashioned” way and sparks of romance will fly. You’re probably more likely to sleep with #3 faster than any of the others because you’re going to feel that powerful connection.


The reason why I tell you to wait is because Guy #3 and Guy #1 look exactly alike. You’ll never know if you’re dating Guy Looking for Love or Guy Who Thinks There’s Something Better On The Horizon. Neither guy is going to show you their cards and the only way you’re going to end up with a boyfriend is by becoming monogamous and signing off of

So Wait. Don’t sleep with #3 until he says commitment. It might seem like a hard thing to do but if he truly is The One, it won’t make a bit of difference.

Comments appreciated

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      anonymous 6 years ago

      Nice explanation about on different characteristics of a guy who is in an online dating site. I am thinking, where am I belong? Commonly, I had respect towards women, if I am going to ask a date on her it is just a date nothing more except if she wants to make it into another stage. ^^