Hypothetically Bold To Ask

, , , | Romantic | June 7, 2017

(I’m invited to a get-together with coworkers. It’s the beginning of summer and a perfect evening, so the small group of us sit outside talking for a couple hours with a few drinks. Everyone there works together except for the wife and a friend of the host, who I have never met before. I’m the last to leave and as my coworker gets up to leave before me, the host follows, and I’m left alone with the friend outside. We start talking, just about what we do, where we’re from, etc., when he springs this one me. For context, I’m female.)

Friend: “So, I have a kind of strange question for you.”

Me: “Okay.”

Friend: “Would you prefer it if, when a guy wanted to ask you out, he was more bold or more subtle about it?”

Me: *smiling awkwardly* “Uh…”

Friend: “So, like, do you prefer it when a guy says something like ’Would you maybe want to go get a drink or hang out sometime?’ or something like ‘I’d like to take you out tonight?’ Which one would you be more likely to respond positively to? Which one would you rather hear?”

Me: *internally panicking, thinking this guy I met about two hours prior and is a friend of my coworker is trying to ask me out right now* “Uh, well, I guess I think it would depend on the guy, how well I knew him, and the situation overall. Yeah, it would depend.”

Friend: “Okay, yeah. There’s this girl back home who I’ve been wanting to ask out for a while, but I don’t know how to do it.”

(I breathed a sigh of relief and went on to give him some advice on his situation. Pro-tip A: Don’t ask strangers for dating advice, because Pro-tip B: They’re going to think you’re asking them out, out of the blue, and get freaked out.)

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