Which two comic strip characters should hook up on Sunday (setting aside, if necessary, their current marital status, their sexual orientation, or even their species), and what would they do on their date?
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Comics I Don't Understand 
Charlie Brown and the Little Red-Haired Girl. They should talk and share a milkshake. And Lucy should hold a football for Charlie Brown, but before he can try to kick it, LRG should sneak up behind Lucy and smack her in the back of the head.
Beetle Bailey’s occasionally boffing Miss Buxley, so I got nothin’ that can top that.
Dagwood & Blondie & Herb & Tootsie, the musical.
Hagar the Horrible and Mary Worth. They should take a moonlight cruise in the Bahamas.
I was going to say Hagar and Blondie. “One of these things is not like the other” dept.
Dinny (Alley Oop’s dinosaur) and Gronk from B.C.
Cassandra Cat from SLYLOCK FOX and Garfield — let’s see if Garfield can find something in life even more interesting than lasagna.
I might suggest Daisy from BLONDIE and Poncho from POOCH CAFE, but as I recall Poncho has been neutered. Still, they could go out for a platonic coffee date at the Cafe.
BTW, for those of you who don’t pay attention to who wrote which posts: this one was from Bill.
I know this is not quite what is asked for, but some strips are dealing in-world with the question of what their characters will do for Valentine’s Day. On The Meaning of Lila, she is working thru the possibilities: third wheel with a work friend, platonic drinking with gay male friend, alone, spending time with sick orphaned child she will eventually adopt …
Dinny (Alley Oop’s dinosaur) and Gronk from B.C.
I’d say Dinny and the other Gronk.
Bobo’s Hagar and Mary Worth nearly made me choke on my lunch. Perfect! The trouble is that Hagar would go home at the end of the evening, and Worth would continue giving him relationship advice for three weeks before she even noticed he was gone.
Jughaid and Samanthy in Barney Google and Snuffy Smith. We need more hillbillies.
Krazy and Ignatz of course. Offisa Pup should take Mrs. Qwakk-Wakk out to dinner for Valentine’s Day so they’re both out of the way. Then Ignatz can throw as many bricks as he wants.
Monty with almost any lady from 9 Chickweed Lane. I have an inexplicable appreciation of plots that match comic losers with sex symbols.
A number of intriguing suggestions! M.A. I agree that 9CL is overheated 🙂
In my first pairing, I forgot to specify the Valentine’s Day date for the couple:
Dinny (Alley Oop’s dinosaur) and Gronk from B.C.
I like to think they’d just go for a walk, viewing the romantic night sky, watching for killer asteroids. . . .
In the 1950s MAD Magazine served up a “Comic Opera”, populated by strip characters singing song parodies. The main plot had Dick Tracy’s girlfriend, a very grown-up Orphan Annie, kidnapped by lecherous Rex Morgan.
In the 70s MAD had a back-cover gag of Blondie & Dagwood, Popeye & Olive, and Li’l Abner & Daisy Mae arriving at a suburban house for a party. In the last panel they came out of the house, shuffled into Abner & Olive, Popeye & Blondie, and Dagwood & Daisy Mae, with the men folk holding up keys.
Much later, when Dick Tracy and Tess Trueheart went through a much-publicized separation in the strip, MAD portrayed Tracy back on the dating scene. He ends up connecting with Blondie, who’s fed up with Dagwood just eating and napping.
Before MAD, there were crossovers in unauthorized eight-page comics … (sounds of a scuffle and a door slamming)
Mel Lazarus’ Momma and Crankshaft. They deserve each other. What would they do? Complain about their kids and their diseases, most likely.