A Better Fate Than Wisdom

You're not an unintelligent person.  You have a wide range of sex-positive vocabulary and tolerance.  You understand that relationships are built on more than sex:  communication, respect, trust, intimacy.  However, there are certain things that still have you turning to Google like a 12 year old.

Last night, talking with a guy online and he talks about one of his favourite ideas about date night, and, as I'm thinking it sounds like one of the sweetest things I've ever heard, he quickly explains that it's just when he's feeling low-key, not, like, going all out.

"That's a lot fancier than my experience."
"What's your experience?"

I cannot bring myself to say, "When you're allowed to eat inside the fast food place rather than having to go through the drive through and eat in the parking lot," so I say, "For his birthday we went to a chain steakhouse.  My birthday always fell during a show, so we never did anything."  And he takes a very long time to type, "That guy sucked."

I know.

"No fun dinners?  No going anyplace fancy?  What would you do if you could?"

In this moment, I realise I need a girl.  Luckily, a friend is still awake, "Hey, what are dates?"
"You like theatre.  Theatre is a date."
"No, theatre is work."
"A date is a thing you like to do and would like to do with other people."
"Ah.  Got it.  Thank you!"

I explain that adventures and conversation are pretty much good enough for me.  "Oh, flirty-type dates.  Cool."  While the conversation moves on, I'm still left wondering what the heck he means.

This morning, I ask for clarification from another friend, what the heck is flirting.  He does eventually answer in a way that makes sense, which I appreciate.  On the way there, I'm left with another comparison I don't understand, "the difference between kissing and making out."

Which, after he disappears, has me on Google all afternoon trying to figure out exactly what this means.  Eventually, I ask my brother, "Teenagers in the car right before the alien/monster/ghost/murderer gets them, what's the word for that?"
"Umm.  It's usually just the scene before the title card, I don't know.  I can look it up."
"No, not the trope, the thing the teenagers are in the middle of."
"Making out?"
"Got it.  Thank you."

That's something I've done maybe twice.  Over a decade ago.  All things at any point after had to lead to his orgasm.  He always said no to anything else.  No means no, right?  No means you shouldn't question it, if it's OK with you, just do it.  Besides, if you say no because you'd rather do something else, and maybe do that later, the whole process will just stop.  Who knows when your next opportunity is going to come along?  So, OK, take what you can when you can.  What does normal even look like?  Why did I let this be OK?

Or, more to the point, why do I still have so much of my self-worth tied up in this?  And why does the only way to change this involve being braver than I feel?