Drunken Hook-Up Does Not Relationship Make

For about 5 months now I've been flirting on and off with a friend. We have had long "deep" conversations and we really seem to enjoy each others company. But nothing ever really happened.

He likes you, but doesn´t LIKE like you.

One time a couple of months ago we were enjoying an evening together and had some wine. Apparently, some of our other friends thought we needed to stop for the night as we were getting a little too close and took us home.

WTF?

If you´re both adult and single, you need to ditch these overpatronizing "friends". A drunken hook-up might not be the cleverest thing to do, but that should be up to you to decide.

We talked on the phone that night though for a couple of hours, had a good conversation and I confessed that I was attracted to him.

If you were after a relationship, skipping the "confessions" and inviting him to a proper date would have been a better idea.

After that night things continued as they were before, he didn't act on the information at all, other than some more flirting.

Weeks went on like this then the big night happened. Once again we were enjoying some wine, but this time we ended up alone somehow. Without normal inhibitions in place, we started fooling around and ended up sleeping together.

You woudn´t believe how common this situation is:

* Girl is hot about boy and is hoping for something serious.
* Boy is hot about the girl but doesn´t want a relationship.
* Things heat up and girl confesses to boy that she´s hot about him.
* Boy doesn´t respond with "Oh, me too, lets date and see what happens", but continues pu$$y-teasing.
* Girl goes along with it, even though she has no idea what´s going on, because she´s doesn´t want to scare him off.
* Boy thinks "Hmmm, she doesn´t seem averse to some no-strings nooky either."
* They end-up hooking up for one drunken night, which may or may not result to a friends with benefits situation.

I don't remember everything that happened that night and either does he.

Do you guys drink this much often?

We've talked about it a couple of times, but never actually discussed the specifics of the night. I really want to know what he thinks about it, but I'm so hesitant to ask. I mean if he wanted it to happen again wouldn't he bring it up? Or is he too concerned about how uneasy I may feel about it?

You´re getting it all wrong. According to him, there is nothing to talk about. He didn´t want a relationship before, and still doesn´t want a relationship now. But I´m sure, if you told him "Hey, want to come over for a movie?" he would. Just skip the booze this time.

To make matters even more complicated, he is quite a bit older than me (25, 45)

Ugh. No, not again!

so I don't know if that plays into it at all.

Yes, it does. But not the way you think.