What is a good way to let a guy down lightly if you’re not interested in him? A couple months ago, I went on a couple dates with one of my former co-workers. We had a great time together, but there just wasn’t any chemistry between us. Or at least, I didn’t feel anything other than general plutonic enjoyment. A mutual friend ran into him at a Christmas party last weekend and he told her how much fun he had with me on our dates and that he should give me a call again sometime – which he did. He asked me to go out to dinner and drinks with him, but I’m not sure how to gracefully go about telling him that I’m not interested in anything romantic with him. Any suggestions?

Ahh… the Christmas party inquiries. What is it about holiday parties that makes people remember past crushes? Maybe it’s the booze. Maybe it’s the fact that it’s f-ing cold outside (at least it’s f-ing cold here in Chicago). I personally think that it’s a mixture of those two things as well as the whole holiday blues. Single people get lonely around the holidays – we have to deal with family members who always ask us when we’re getting married, why we aren’t having children, and stupid comments about how we’re not getting any younger. A Christmas party induced hook-up is a good way to warm up the soul before getting shot down by frigid family members. Letting a guy down lightly around the holidays is a very delicate situation.

And if there’s an adjective that I like to use to describe myself, it’s delicate. I also like to use the word “dainty” to describe myself. But seriously, it’s very difficult to get the “Hey, I want to be friends and I absolutely do not want to date you” message across.

A couple weeks ago, I went to a holiday charity event at the Second City. I always end up running into people that I know at these events – I guess that’s what happens when you are friends with improvisers. I ended up running into a very good acquaintance of mine. This is a guy who I met at one of the first parties I ever went to after moving to Chicago. A good guy. I like him a lot and I always have a great time talking with him when we run into each other at improv/comedy related events. When friends like this hit on me, I’m usually 100% oblivious. This friend asked me for my number and said that we should go out for drinks sometime. I said that I’d love to get drinks and we exchanged numbers. The next day, I started getting nervous that this guy thought more of the situation than I did.

In these situations, it’s always best to be honest with the guy. I sent my friend an e-mail with my schedule for the next couple weeks and then straight-up asked if he had any romantic intentions for the evening. I then explained that though I think he’s a totally cool guy, I’m just plain not interested in anything romantic between the two of us. Being the clever and funny guy that he is, he explained that he is interested in romance, but that he was okay with me just wanting to be friends.

So, here is my advice to you. When the guy calls again to finalize plans, just ask him straight out if he considers the two of you going out a “date” or if it’s just going out for drinks. Then tell him that you really don’t want it to be a date. He’ll probably make some sort of conceited dude comment about how you’ll change your mind. Instead of dinner and drinks, maybe just suggest getting a drink or two later in the evening. If he wants to see you, he’ll be fine with going out for drinks, but you’ll need to be strong because he’ll probably still try to get you to go home with him. Maybe go to a bar where you’ll know some of the clientele or at least the bartenders. That way you’ll have a good time having drinks with this guy… and you’ll have backup incase he forgets that the two of you aren’t on a “date.”

Also – don’t shave. Just to be safe.

… and to all a good night,

Miss Single USA