It’s arguable one of the most exciting but also confusing parts of dating: that in-between time after you’ve met someone, and before you’ve actually gone on a date. The gray area.
You’re pretty sure they like you…but you’ve been wrong before. And even if they do like you, how do you parlay heavy flirting into an actual date?
At some point, someone has to ask the other person out. Traditionally, this is done by the guy. But asking someone out is really terrifying, so he’s probably only going to do it if he’s absolutely, positively, beyond a doubt sure that there’s a good chance you’ll say yes. Otherwise he may chicken out. This is why it’s essential that you make it pretty clear to the guy you’re flirting with that you’re receptive to the idea of his asking for your number or inviting you to hang out.
And even then he still might not be able to pull the trigger (or he might be completely clueless as to your interest in him.) In hat case, take matters into your own hands and ask him out yourself. You don’t have to do it immediately. But if after two weeks of flirt-texting you’re frustrated that it’s leading nowhere, take the bull by the horns and invite him to hang out with you.
There’s a sneaky way to ask a guy out by actually throwing the ball back in his court, and it’s this: Simply invite him to invite you to go out. Say: “Let me know if you want to grab a bit sometime.” That way, you’re suggesting the date, but he’s the one who will actually have to ask you out…by “letting you know” that, yes, he does want to grab a bit.
Another super-simply way to ask a guy out is to always keep an eye out for great date activities – even before you have the date. If here’s a concert or a play that you want to check out, buy two tickets. That way, if you happen to meet someone, you can just say, truthfully, “I have an extra ticket to ____ next week. Do you want to come?” And keeping on top of events and activities in your area is great conversation fodder that can easily be transitioned into an invitation. (“Are you doing anything for Halloween? I’ve been reading about these ghost tours in the East Village that seem insane…”)
Still unsure as to whether you should ask him out? This flowchart will help you decide. Click to enlarge.
Adapted from Modern Dating: A Field Guide
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