I've been going through the second DC Comics TOS series lately, and having gotten to the annual written by George Takei and Peter David, something struck me... apart from the brief glimpse in Star Trek Beyond, has Sulu ever had a romance that wasn't an absolute tragedy? I can think of at least four major relationships for Sulu in Trek lit, and they all ended in death or might as well have. The Captain's Daughter, "So Near the Touch" (the DC annual), Allegiance in Exile, and Year Five. There are probably other examples. Heck, it even happens in the New Voyages episode "World Enough and Time." Even though Kirk, Spock and McCoy all had serious relationships that ended tragically, the ratio wasn't nearly as high as Sulu's. Did poor Hikaru ever catch a break? Or is being a serious love interest for Sulu (not just merely flirting, like Uhura) a universal death sentence?
Wasn’t there some flirtation between Sulu and someone in The Weight of Worlds? It been a few years since I read that book, but I want to say that it at least did not end in tragedy, even if bound by canon to not have a happily ever after. Although I’m just amused enough to call this all evidence that Sulu really should stick to dating guys if his interest in women seems to be a(n almost literal) kiss of death... :P
The Sulu/Ayal romance wasn't so bad. A war did start between the I'Qosa and the Lo'Kari, but Ayal didn't die and he/she parted with Sulu on good terms.
When they left Ayal's planet, IIRC, they weren't even sure if Ayal was alive, or if anyone was going to survive.
Mandala Flynn may be an exception that also proves the rule! The Entropy Effect shows the start-ish of their relationship and, in one timeline, the end when she's brutally gunned down by Georges Mordreaux. But, in the "real" timeline, she lives and we never do learn how it ends.
The Wrath of Khan and Search for Spock novelizations implied that Sulu and Flynn were still in touch with each other and on good terms, at the very least.
Cannon is Sulu had a daughter. From what Scotty said is that Sulu made the time for a family. Maybe Sulu didnt accept a captaincy till Debora was in the academy. So looking at age, demora is.. 22? In 2293. So 2271 or so born, so after tos, during the refit she was born. Not up on trek lit for Sulu. But know demora mother left or something. I'd rather believe that he had a family at home, and us why he took the academy job in ST2 to be near home.
In the first volume of the DC comics he and M'Ress had a drunk hook up. It ended awkwardly, but not tragically. late in the second volume I remember 2 female officers fighting over him Betty & Veronica style, then choosing their friendship over pursuing him.
In The Captain's Daughter, Hikaru doesn't know about Demora until the mother dies, and Demora is sent to him (at age 5, I think). He does pass up an assignment on the Bozeman to stay at the Academy so he can raise Demora. Star Trek Unlimited #9, however, is a story set during the five-year mission where Hikaru shows Chekov a picture of his infant daughter.
FWIW, I wouldn't really consider either of those a "serious romantic interest." As you say, the M'Ress thing was a drunken one-off, and the two junior officers fighting over him both transferred off the ship before anything could come of it. Neither one of these even rose to the level of a "girlfriend of the week" on TOS.
M'Ress was actually redrawn as an antelope woman, M'yra (named for Peter David's first wife) in the first issue of DC's Series II. So the intention was for their relationship would be longer. The renegotiated licensing contract put TAS characters off-limits. (And Arex became Ensign Fouton.) M'Ress dismissed by Ian McLean, on Flickr ["Amazing Heroes" magazine #170, Aug 1989, page 99]. M'yra replaces M'Ress by Ian McLean, on Flickr
There was a DC issue where Sulu was given a romantic backstory with his cousin, so I'm guessing he doesn't make the best choices. Even in the Kelvin Universe his family almost died on Yorktown.
There are many cultures around the world where marriage between first cousins is permitted, including the United Kingdom. Wikipedia says it's legal in Japan, though the occurrence is declining in recent years. Anyway, that's the least of that issue's problems. "Giri" is a mess of exoticizing Japanese stereotypes and cultural ignorance. One of many works of fiction from the period whose Western authors thought they were celebrating Asian culture when they were actually stereotyping the hell out of it. (But then, the same thing happens the other way around -- judging from the Super Sentai franchise, the Japanese seem to think most Americans are cowboys.)
I was reading some older comics not too long ago, and if I'm remembering correctly, Sulu was in a relationship with Maria Morelli over a few issues. They ended up breaking up, but it seemed amicable... and nobody died.
Yep. Sulu had a romance in WEIGHT OF WORLDS. Come to think ot it, I threw some romance his way in THE ANTARES MAELSTROM, too.