Dear Sasha, I have been seeing this guy for about a month now. He’s a really nice guy, sweet-as-the-apple-pie-with -a-homemade-crust-he-baked-me, kind of nice guy. I just really am not feeling a great connection and think we would probably be better off as friends. So I was going to tell him as much, but me and my friends were throwing this Halloween party that him and his housemates were all planning on attending and I figured it would just be less awkward for everyone if I waited until after to end things (we're both grad students in the same program so we have a stupid number of mutual friends). This party got a little rowdy to say the least and we ended up boning, but I also had a really good time dancing and hanging out with him, so I decided to keep seeing him. Well last night he had me over for dinner, he made this incredible lasagna with pear turnovers for dessert (!!), but I just wasn't feeling anything. I know I probably should have just gone home but he had been so sweet...anyways we had (sober) sex for the first time and it wasn't great…both times he didn't really last for more than two minutes. My problem now is that I know I need to end things but I don't know how. I don't want him to think that the 2 minute thing is the reason, because it really isn't. I want to be friends with him, because he is such a great guy, or at least be able to be around him without it being super awkward because we have so many mutual friends.  Sincerely, Feels Like An Asshole

If you feel like an asshole now, trust me when I tell you that you’ll be one gaping giant asshole if you keep stringing this guy on.  Obviously buddy has some real feelings for you and you’re not doing him or you any favors by eating his food and having unsatisfactory sex.    

I know it’s not fun to tell someone you don’t like them in ‘that way’, but if the spark isn’t there, it just isn’t.  I know you know this, but what I want to get across to you is that I don’t think you should talk yourself into feeling guilty over this.   

So what to do…

I’m all up for honesty, you know that, but when it comes to breaking it off with someone you actually like, I don’t think you need to get super real and list off every reason why you’re not interested (i.e.,  don’t bring up the fact he’s a one pump chump).  Just tell him that you’ve totally enjoyed the time that you’ve spent together, and you think he’s awesome, but being friends is the better way to go.  That’s all that needs to be said.  

After that, it’s up to him if he wants to be friends with you or not. That’s just the chance you took when you jumped in the sack with him.  But the longer you wait and drag it on, the less favorable the outcome for you.  So get on it.  

(Lainey: this photo applies…again.)