What’s the best way to deal with rejection if I ask a guy out?

I think I’ve finally worked up the nerve to make the first move on a guy because I’m tired of wondering where I stand. We talk a lot, he’s expressed very pointed interest in spending time with me, but the few times we’ve gotten together in person, he’s never even come close to making what I’d perceive as a move. Add this to him becoming hard to pin down when the time to get together approaches, despite earlier discussions initiated by him about specific plans including dates, times, and activities, and I go back and forth on whether he’s interested. I don’t want to speak for him, but I’m pretty confident in asserting that we’re both more socially awkward, or at least shy, than not. I’ve convinced myself that resolution is more important than pride which is pretty much unprecedented. However, I want a graceful exit strategy should he reject my overtures.

What’s the best way you know to play off rejection of a move to minimize awkwardness? I’m okay being friends with this guy if he’s not romantically interested in me. I like him and would be open to seeing where things could lead, but if that’s not what he’s looking for, I’m comfortable with that and won’t pine away. It’s the immediate situational awkwardness that I’m worried about. I know I can get over the rejection itself, but the remembered embarrassment is a different story. How do I play it off in the moment to limit the awkwardness as much as possible and make it clear that I’m largely cool with what just happened and would like to continue being friends? All I can come up with is a playful comment along the “it was worth a try” line and that seems weak.

I know a positive attitude going in would probably be a far better way to approach this, but if I don’t have some sort of contingency strategy ready, I know I’ll never follow through on making the move.

The best way to play off rejection is after being turned down, fling yourself off the nearest precipice, sustain a head injury, and get amnesia. It’s horrible. I asked a guy out one time because his sister had insisted that he thought I was the most amazing person to set foot on this earth, and one night he drove me home from a party and I was like, “Hey, we should go out some time,” and he was like, “That would be great but I just started seeing someone and I wouldn’t feel right about it,” and I immediately died from embarrassment and have lived the remainder of my life as a ghost. I want to crawl under the bed just thinking about it.

I know you didn’t ask me this, but I don’t think you should go out with this guy. You’ve been in a situation several times where he could have made a move and didn’t. Call me old-fashioned, but I think if he wanted to, he would have. But even more worrisome is this: he’s “hard to pin down” when you’ve already made a plan? That’s not socially awkward; that’s rude.

Maybe just be friends with him and he’ll put the moves on you one day. Otherwise, there’s no point in putting yourself out there for someone who can’t be relied upon to follow through when you make plans. People don’t behave better over time—they get worse. Imagine what he’ll be like once you start dating.

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