Dear Dating Mom: Is the 3rd Date Long Enough to Wait?

single woman after one night standDear Dating Mom:

I’m divorced and I recently met a guy I really want to sleep with. But I also want him to stick around for a while. I've heard that the third date is when it’s okay to sleep with a guy for the first time, is that true?


Three IS a Charm, Right?

Dear Three IS a Charm:

True, false, maybe, who cares?!

I have no idea how old you are but if you’re anything like me, every adjective used to describe you ends in a “y”. Saggy, wrinkly, horny, and over forty.


Now, although the first three are enough to make you want to hang yourself, the last one ain’t so bad because with age comes the ability to decide whom you want to sleep with and when and not have to worry that somebody is standing outside on your lawn with an abacus adding up how many partners you’ve had.

And that ain’t even the best part. In case you forgot, 10th grade has come and gone and it’s not like the next day, while on your morning walk ... of shame ... you find yourself running into the head cheerleader. And then having to endure an entire day, or days, of the female part of the student body talking about what a slut you are while the male portion tries to figure out why the hell it wasn’t one of them.

Speaking of the “walk of shame,” I stand corrected. The shame part would come in because other people notice you. Doing it when you’re in your 40s? Sadly, you could be walking back to your car at 7:30 in the morning, decked out in a cocktail dress and heels, screaming at the top of your lungs, “Hell yeah, I just got laid and I’m not even sure he’ll remember my name!” and frankly, no one would even care. Some might even be jealous. More specifically, those of us who are spending that time of our morning loading our kids into the car for the ride to school while decked out in the chocolate stained sweatpants we wore to the previous night's candy festival. (That would be the festival that was held inside our pantries where it just so happens we were the only ones in attendance.)  

That being said, how long you wait to sleep with a guy is no guarantee that he will stick around. I once waited several weeks before I slept with this one guy. You know how long we ended up dating? Several weeks and one day. Never mind that I medaled in the ball massage department, twice. He could’ve cared less. Then again, I know many a happily wedded woman who slept with her husband on their first date and then fully believed she would never hear from him. However, again, in my case, all the worrying was absolutely justified but, who knows, maybe you’ll have the same luck as they did. 

At the end of the day, however, you need to do what feels right for you. Unless you're a psychic, you can't predict what he will or won't do. The only thing you have control over is where he takes you to dinner ... maybe.

Are you a single mom with a question about dating/sex/love? Or do you just want to try to trip Jessica up? Leave her a question in comments or you can write to her directly at


Image via Anton G/Flickr

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