Dear Mr Knightley,
About a month ago I began stage-managing for a play (basically I’m the person that keeps everyone in line and makes sure there’s a show to put on after rehearsals are over), and I quickly became attracted to one of the actors. He’s funny, kind, thoughtful, and extremely talented. At first I didn’t think I had a chance (aside from being generally out of my league, he’s also about five years older than me), but we’ve become more and more familiar with each other. He’ll tease me, and joke with me, and recently he’s sought me out to tell me a story just because he thought it’d make me laugh (and it did).
I’ve never really been serious about anyone, but I know I’d be kicking myself forever if I didn’t at least try to…make something of this. Anyway, there’s only a week left of the play, and then I’m not sure if I’ll see him again. I wouldn’t exactly call us friends, so how should I go about…becoming a part of his life, I guess? I don’t want to just ask him out and have that be the end of it. I want to get to know him. Can you help me?
It can often be difficult to try and navigate the frightening world of relationships. Especially when they begin to bud in a “professional” type setting. You are absolutely right in wanting to take things slow and establish some credibility first.
You might wish to try and ask him to coffee. This does not have to necessarily be a date. It’s simply coffee. During the conversation, try to find out as much about him and his interests as you can. Identify areas of common interest, and ask how he goes about pursuing them. Eventually the subject of events, or meetings or gatherings or conventions will come up. This is your golden opportunity to spend more time with him. To slowly and carefully integrate yourself into his life.
This will also give you a chance to get to know him better. Which means you’ll be able to really tell if you want to be more than friends.
Best of Luck,