Is This Invitation Creepy? or Just Awkward?

Dear Papa Bear,

I had something happen to me tonight that requires a little mulling over. Last year I got involved in a community theater production and I met this guy about halfway through the rehearsals. The night I met him it was bad weather and he was nice enough to give me a ride home and we ended up exchanging numbers. Now I merely consider this guy to be an acquaintance, I only saw him sporadically before the opening night performance, and I know very little about him other than he works as a music teacher. 

So the production ends at the beginning of May, and oh, about eight months go by and then tonight, the guy in question texts me and asks me if I want to go night sledding with him. I was a little confused at first before I remembered who it was. Well, naturally I was hesitant and I mentioned having to work at the time he wants to meet, but he still insists on meeting up for night sledding. Furthermore, it’s in an area that I don’t know very well. I feel like he’s pushing me to meet up when I hardly even know him. Papa Bear, any advice you have on how to deal with this will be greatly appreciated!

Sincerely,

A Confused Coon

* * *

Hi, Coon,

As Obiwan Kenobi might have said, “Trust your instincts.” That invitation is not at all normal, and you easily sensed that. All kinds of red flags went up, so I think you will agree with me when I say that you should not take him up on this idea of sledding in some area that is unfamiliar to you.

This doesn’t mean that he is necessarily some kind of creepy stalker. It could be that he is simply a socially awkward person who doesn’t know how to set up a first date. Perhaps it took him months to work up the courage to ask you out and he suggested the sledding because it is something he is familiar with.

Either way, your best bet is to politely decline this particular idea, but, if you have any interest in this guy at all—as friends or otherwise—make a counterproposal. Invite him to come along as your guest to a party or other meeting with a group of friends of your own, or perhaps you share some theater friends and you can all do something together.

If he declines your counterproposal, it could be that the initial feeling of suspicion is correct and you should just avoid him. If he accepts, go with it and see where it takes you.

Hope that helps!

Papabear