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Would you go on this date?

Asked by sliceswiththings (11723points) June 26th, 2011

Darling Jellies, I prefer to be the one giving the dating advice, but this one is really stumping me. It’s also super long, sorry!

The guy is a regular at the café I waitress at. He comes in every morning for coffee and we chat. The boss said that he had asked about/expressed interest in me.

I ran into him last night and we talked a bunch. He straight out said/asked, “The new Woody Allen movie is in town. Want to go see it sometime?” I said yes, because I do really want to see it! Perhaps he’s just looking for a friend, but it sounded like a date to me.

Here’s the thing: I am terrible at dating (by traditional standards). I usually promote a very romantic beginning, go out with the guy for a couple months, don’t feel strongly about it, then move on but usually cause some kind of drama. This guy is different from the others because he is gasp 15 years older than me. I feel like he must be more serious about relationships than I am at my young age.

But here’s the thing: I’m pretty sure I don’t want to be in a relationship with him while I’m here (just for the summer). I could either:
A. Go on the date, go on more dates, date him anyway;
B. Go on the date, try to bang him a couple times (what I’m really after), find a way to worm myself out of a more serious situation and hide in the basement whenever he comes for coffee;
C. Not go on the date (but I already said I would sometime, so that would be obvious if I didn’t).

He’s super super nice, and is a well liked member of my community. I would hate to start something with him, back out, then have it be awkward all summer when he comes for coffee.

What would you do in this situation? Has anyone been in a similar situation? Thanks!

P.S. He brought me strawberries from his own garden this morning :)

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