Anytime you proposition someone, whether it's a long shot or a "sure thing", disappointment is a possibility. You shouldn't stop propositioning people for fear of disappointment, but at the same time that possibility has to be in your mind, and you have to be prepared to manage it. If you can't, if you make it the other person's problem, then that's a consent issue.
You have to practice the polite, friendly, "ok, no worries!" and then peace out. In an ideal world, you're super philosophical about it, you don't even feel disappointed. But in the real world - it usually means hiding it.
After that you manage yourself: maybe this looks like texting a friend to hang out, maybe it looks like cueing up a show or videogame you're excited about, maybe listening to country music - the music of pain - maybe doing something creative, maybe taking yourself out to dinner. But it's so important to learn to like your own company for such times - you must never put your hope in someone to save you from time with yourself.
I have to admit, when I see or read about men not holding it together in the face of rejection, eg many accounts of male behaviour on fetlife, I get a bit smugly judgmental. A part of me is like, "bro: man up!" But it is a tough thing to learn, and I do think men don't get as much support around managing their feelings around that - I feel like women are at least offered more advice about that.
And on the flip side, I know unregulated men are often at least a whiny, passive aggressive pain in the ass when disappointed, and not infrequently scary. There's even a micro trend of "incel horror movies" about men trying to take away women's ability to reject them, eg Obsession or Companion.
Interestingly, the non monogamous, slutty, granular-consent world of kink offers the chance for many new types of disappointment. Maybe someone only wants to do one limited thing with you, when you would like to do more. Maybe someone is fucking half the people at an orgy, and you're not in that half. Maybe they wanted to have sex with you for a while, and now they only want to hang out as friends. Maybe they only want to play with you once in a while, when they're in a certain mood. You have to be so real with yourself, and the other person, of whether that works for you - or if you need to take a step back, and switch into getting-over-that-person mode. But ultimately it's a beautiful thing, that, even when one side is thirsting for more, these customized-consent hookups can bloom. It's so good when you can look into your heart and find true appreciation for your time together, whatever form it took.
Besides just managing your own emotions, which therapy and other kinds of self help can improve, I know two things that make this better.
The first is a feeling of abundance, that there are lots of possibilities around, multiple people in the getting-to-know-them pipeline. That means hustling: getting out there and meeting people, even when you don't feel like it. Sometimes that means finding the right community, even when it takes significant travel time. And then proactively seeing if there's more there with the people you meet.
On this point, something the often-toxic PUA world gets right is that fixating on one person, what they call "one-itis", like it has to happen with my cute coworker or neighbour or rope instructor, is a recipe for disaster: both for having flatlining love and sex life, and also for putting pressure on someone to not let you down. (I hate moves and TV shows that buy into this trope, like to me How I Met Your Mother is a horror movie) Leave that person alone and think about how to make abundant possibilities.
The second is, this just gets easier with time and experience. I've had a lot of sexual and romantic disappointments, some of them super embarrassing. And I survived.
But I've also had lots of things work out. I've had people I thought were way out of my league be into me, I've had things just happen out of the blue with no effort. I've thought that something was definitely not happening, only to discover that the person was just busy or distracted and pinged me back much later (and being super chill with the initial silence or "no" vastly increases the chances of that happening). And I've been the one to disappoint other people - and being on the other side of it has given me a lot of compassion for when people have to let me down.
I will say, if you're in some kind of woe is me spiral of, "it never works", I'm doomed to always be the one who's disappointed, there's bigger problems going on, and those are not the fault of any individual person rejecting you - it's a signal that it's time to work on yourself.
Don't let fear of disappointment stop you hitting on people, in fact if you're a conscientious, consent aware person you probably could be doing it more. As long as you're doing it in appropriate ways and times, it's all good practice in surfing that extremely human and unavoidable feeling - disappointment.
PS Sex blogger and podcaster Kate Sloan has a lovely piece about appreciating one-sided, aching crushes for their own sake, as fuel for self-improvement and creativity, well worth a read.
