Dear Jewish Fairy Godmother:

I’ve been single for about three years. Some dating but no one special.

Recently I met a friend for lunch; she’d bumped into a client while

waiting for me. We all stood around chatting for a bit before he peeled

off. I didn’t pay too much attention to him, other than getting his vitals

(professional, once divorced, one grown child). I didn’t think too much

about it until I got a call from him last night to ask me out. That part’s

fine, as I might in fact want to date him. But it was clear in the

conversation that my friend had told him far more about me (I’m

talking vivid details, not broad strokes) than I would ever have

disclosed on a first date conversation, all without even telling me that

he’d asked for my number. I feel a little vulnerable with him and

definitely angry with her, who said she “just wanted to surprise me.”

Do I proceed or back away?

More than Surprised

 

Dear More than Surprised:

Blame her more than him. For her I recommend a mix of education

and appreciation, plus a tablespoon of guilt. Appreciation because she

really did you a favor by helping you meet someone eligible and

potentially interesting. Unfortunately her enthusiasm went way

overboard, in a troublesome and invasive way. Clearly she has

boundary issues. Make it very clear to her, for now and the future,

what’s okay to say and what’s off limits. Okay might include a little

more than name, rank, and serial number (or in this case, job,

divorces, and children). But part of the fun of dating is learning

someone’s stories from them, especially because their personal history

is theirs to share. And in her urge to sell you, she robbed you of both

privacy and fun.

 

That said, think of it as research instead of prying. Don’t hold it

against him. Instead, try to be playful when you do connect. Say

though your friend has given him many headlines, you’re not sure she

or he got it right since you weren’t part of the convo. Ask him to

match you story for story, in part to level the playing field, and in part

to correct any misinformation. Act like the proud and confident person

you appear to be. The good news is that if she’s blabbed any deep,

dark secrets and he’s still interested, you may be onto a good new

prospect.