Thinking about all the... let's call it ex-shipping I'm doing in terms of Superbat. I've never had a ship where I'm like "here's a list of people they dated before and how that affects them now", but here I am.
This is all based off my little sandbox canon, just for fun.
Bruce
Harvey Dent - Bruce's most serious, deepest romantic relationship of his past. They were very close to becoming Gotham's biggest power couple. Then... Two-Face happened and everything fell apart. A relationship characterized by tragedy, longing, and lingering love.
Oliver Queen - They never actually dated, but they definitely have had sex on multiple occasions. Unlike most canons, they didn't drift apart after their youth, staying in contact even as they both went vigilante. Friends with benefits, though less so now that Ollie has Dinah.
Selina Kyle - Second closest romantic relationship, and the first that started as Batman instead of as Bruce. For a long time was cat-and-mouse (hah), will-they-won't they, before briefly becoming a real relationship after their identities were revealed to one another. Selina tapped out after Bruce adopted Dick, having no interest in becoming a mother. They're still friends and sometimes allies as the situation calls for it.
Lana Lang - His high-school romance. Clark had it in his head that they'd get married and be sweethearts like his parents, but when it came time for college, they realized they had very different ideas of where they wanted to go in life. They've mostly lost contact, but think of one another fondly.
Lori Lemaris - His major college romance. Clark wanted to marry her, caught up in the same ideals about marrying young and having a family he brought with him from Kansas. That too got brought to a halt by their circumstances when she turned down his proposal and broke his heart. Though it was painful for a while, they reconciled afterwards. They bonded as two outsiders looking in on humanity, and eventually settled as good friends. Clark visits multiple times a year, and is supportive of Lori's new marriage with Renal.
Lex Luthor - After Lori, Clark gave up on the traditional romance. So when Lex showed interest in him but told him to keep it hush hush, he buried his romantic ideas and accepted being the hidden lover. There was genuine love between the two of them, but unfortunately Lex is Lex, and is terrible even on his best behavior. That relationship ended in a ball of flames and trauma.
Lois Lane - Lois was infatuated with Superman. Clark was infatuated with Lois. The happy ending would have been that after the reveal of his identity, Lois would be infatuated with Clark. It didn't work out that way. Lois had built a fantasy of a perfect, self-confident man who was there when she wanted him, bringing adventure and excitement into her life, and then went off on his own. But Clark isn't actually that man. They dated for a while, and she realized that Clark would simply accept that she wasn't the partner he truly hoped for, the one who would notice all the little things, would offer him comfort and care, would give him the family he longed for. Clark would stay with her anyway. She loved him enough to consider trying to compromise, doing her best to become that person. And then she realized it wouldn't lead to a spot where they were both happy. So she broke up with him. It hurt them both, but in the end there was something similar to relief. They're forever important to each other, just now in different ways.
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