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Tom didn’t even support gay marriage. At the time it became legal, when he was in college, he watched his friends — not just the guys he could see wavering on the issue because sometimes they liked sucking dicks, and were willing to fuck up their chance to make real money to keep doing it in the future, but his normal friends — decide to support it, or at least waver on the idea. He just didn’t get it, the decision to decide to wake up next to another man every day, to say to someone at a cocktail party, “oh, my husband’s right over there,” and see their estimation of him fall. It’s not, he admits to himself, at least sometimes, that he doesn’t understand the actual fucking part. He’s let himself try it a handful of times, a sparse handful, after drinking enough to offer a generous amount of plausible deniability.
It’s not that he doesn’t like women too. He was worried, after one sweaty night with his freshman debate partner, that maybe he was really screwed, but he found quickly that no, it was fine, he was just as happy in bed with a woman, maybe more. Certainly he was more happy in general, meeting first his college girlfriend’s parents, going on vacation with her and her friends. When they broke up, he was happy with his business school girlfriend, with their plans for the future, with the way they said “we” when talking about what they’d gotten up to the weekend before, with her long blonde hair.
He didn’t have to think about it much after that, gay marriage, or gay stuff at all, not least in regards to himself, because it didn’t matter: what he really likes is monogamy, is being on a team, and he’s never had to be single for very long.
He liked the look of Shiv Roy even before he knows who she is, although he always had known what she looked like. What he’d really thought when he first saw her was how much she looked like Shiv Roy, daughter of the Roy family, and how even looking like her was attractive. When they met, he’d thought he fucked it up. He’d seemed too nervous, too awkward. But somehow it had worked. He had charmed her.
After that point, he let himself relax, or at least, worry about new things. Shiv’s family, his new job, how to propose, what a fitting gift would be for the scion of a media empire. He’s making a lot of money—a lot—the kind that those cocksuckers in college would never make, because no one would hire them if someone like Tom was around instead. Whenever he sees Shiv in the evening, in lingerie that costs more than some transatlantic flights, he feels a warm rush of attraction, a bright glow of heterosexuality.
And then he meets Greg, who is awkward and naïve and immediately closer to the Roys than he is, and manages to fluster Tom to the point that he cannot decide whether to be friendly or dominant. He hears himself have a conversation with Greg—conversation isn’t the right word, he’s just talking and Greg is reacting—and hears himself ask Greg, “Would you kiss me?”
It’s a joke, he’s just joking around, but the part of him that’s listening wants to know.