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"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.
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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.