It’s cool when a friend wants to hook you up — for one thing, you can be pretty sure the guy’s not a loser. But, there’s a higher awkwardness potential if it doesn’t work out, so ask your matchmaking pal these questions first (consider this your bad-date insurance).
“Why do you think we’d be a good match?”
Many people assume that since they get along with both of you, you’ll be into each other, too — not always true. This question forces her to articulate your commonalities. Watch out if your friend seems hard-pressed to answer.
“What’s his recent dating history like?”
If he just got out of a long-term thing or hasn’t had a girlfriend in several years, that might mean he’s not looking for anything serious at the moment. That’s fine if you want a casual relationship, too. But, you should know what you’re getting into up front.
“How would you describe me to someone?”
Your friend’s response reveals the type she thinks you’d go for. For instance, she replies that you’re sweet and quiet… but in fact, you like a guy who’s edgy. The one she’d pick for you might be way too understated (read: boring). It also clues you in to what she’s told your prospective date about you.
