Not that long ago I offered what advice I could about how to ask out your crush object.
The next worrisome “first move” is probably gonna be the first kiss.
I can tell you that the first kiss is easiest after it’s reasonably clear that you both fancy each other. You can’t know for sure, you can only get a general sense.
I can tell you that timing is important – a first kiss is a good punctuation mark. At the end of a date, at a transition point in the date, even a the start.
I can tell you that asking first is a good idea, because it gives the person an opportunity to decline gently and doesn’t build unnecessary “you kissed me when I wasn’t into it” weirdness. For example, if you’re walking down the sidewalk, don’t STOP and FACE the person and create a moment where if they say no you have to turn away and start walking again. Just, as you’re walking, gently mention that you think kissing might be a good idea and you were interested to hear their thoughts on the subject.
(Is this cowardly? Well yes, in a way. But it spares not just you but the other person the awkwardness of a failed kiss attempt. It’s generous and considerate of you, as well as being craven.)
However, I want to acknowledge that being besotted can interfere dangerously with your ability to think rationally about timing and asking.
Like, when I’m into someone, my brain just can’t put it together. Reason flies out the door and I’m left in the turbulent, noisy waters between urgent hopes and crushing doubts. My own internal experience takes up so much of my consciousness that I can’t gauge whether or not the other person is feeling anything similar. I assume they’re not, because history has taught me that that is the statistically more probable outcome, but, you know, they agreed to go out with me, so… I just don’t know and I’m nervous about it and all the “Emily you suck!!!” voices in my head get loud and it’s just awful.
So I sympathize.
That said, I’ve had one notably successful application of the rules:
I was in lying on the couch and he was sitting on an adjacent chair and we were watching TV. I muted it after the show (pretty sure we were watching “South Park”) and said what I had carefully planned earlier in the afternoon. Something like:
“So I’ve kind of felt like there’s been some should-we-kiss kind of tension between us for a little while, in addition to the very fun friendship we have, and I was just wondering whether or not you were noticing the same thing or if that was just me or….”
Being a very nice boy, he responded by leaning over and kissing me. Which was nice.
What was particularly effective about this strategy is that if he had not been feeling the same, the way I presented it offered him a gentle way out – we could preserve our friendship and I could let the kissing thing go.
(Depending, of course, on my ability to cut off my burgeoning attachment, which is something I’m pretty good at but which is really very difficult for some folks.)
So: have some sense that the person “likes you likes you,” wait until a transition moment during the date, and ask first, leaving a comfortable way for the other person to say no.
I’m afraid I’ll need a whole additional post on what to do with the bruised and tattered remains of your heart, in case they do say no.