I always get sweaty and anxious (SO different from my normal resting state) when I'm writing a plans-making e-mail and have to propose when to meet up with someone in relation to a hard stop (e.g. a drinks date she has at 9pm, a reading we're both attending at 7:30pm).
In my experience, you usually end up sending one of three kinds of e-mails. Let's say, for example's sake here, that you're meeting up with your friend who has to be at the Big Apple Circus at 8pm (what better place to LIVE IT UP than the examples in one's blog posts, right?!):
1) Proposing a somewhat late meet-up time at the risk of seeming like you're trying to limit the amount of time you'll be spending one-on-one. "Why don't we just meet at 7 by your thing and find somewhere to grab food?"
2) Overdoing it in the other direction (you'd be up for spending weeks and weeks together if you could!) — "Maybe 6?? Is that too early?! :P" — knowing full well your friend will suggest pushing it back ("Could we actually do 6:30? I'm going to be, like, coming from uptown.")
3) Being comically indecisive in an attempt to completely force the decision on the other person. "Anything works for me! 6? 6:30? 7? Hahah! The possibilities! I can't believe you're going to the CIRCUS!"
No option leaves you feeling particularly great. You either worry you've offended the person (a fear that increases with each passing minute you don't get a response) (#1), lament that you'll now have to cut your early evening "mess around on the internet on the couch" time by an hour (#2), or sigh that you've simply delayed any decision and that there will now be at least seven more e-mails back-and-forth (#3).