Dating discussions in contemporary romances can be summed up in one sentence:
"Dating stinks!"
The best of the contemporary romances will deliver a kind of comedy of errors surrounding the topic: better to laugh than to hide under one's bed.
Here are M/M examples:
Little Library by Kim Fielding: the date at the restaurant is a maelstrom of classic mishaps, from the trope of spilled water (hey, it even happens to Randy in Home Improvement!) to too loud confessions to interrupting family members.
Good line: "Simon stared at the menu with a degree of concentration usually reserved for students taking final exams..."
"The Date" by May Archer: the date is confused by mistaken identity--consequently, an argument ensues even before the date begins.
"How to Howl at the Moon" by Eli Easton: there's an actual first date but in many ways, the first date takes place when Lance shows up at Timothy's place in dog-form for surveillance. Since Timothy proceeds to treat Lance like the cutest dog ever--and Lance is a rather starchy person who does not see himself in that way--Lance's long-suffering reaction is very funny and, yes, very cute. And dovetails quite neatly with what we all assume: My pet understands--and tolerates--me more than anyone human.
Great line: "He makes you dance."
Many stories by Jackie North have a rather sweet, lightly humorous first date. There's also, "The Christmas Eve Craigslist Killer" by Jill Wexler, which is, in many ways, one long date, filled with clever dialog. I review it more here.
There is a line between humiliation and hilarity. In Twelfth Night, Malvolio's attempts to flirt with Olivia are pure humiliation. Although he (mostly) deserves it, it is still somewhat discomforting.
What makes the other above examples funny but not discomforting is that the characters use the mishaps and misunderstandings and rapid-fire dialog to learn more about each other. They problem-solve intelligently.