Chapter Text
Poor little rich boy, all the couples have gone. You wish they hadn’t, you don’t want to be alone.
Roman Roy would be the first to admit that he was shit at relationships. (Maybe not the first — Shiv was usually the one doing the honors on that front.)
And wasn’t like he’d had great examples growing up, anyway; Mummy and Daddy dearest weren’t exactly a love story for the ages.
All the same, his siblings had managed to snag relationships of their own without too much trouble, despite springing from the same loins from which he, Roman, also came. Shiv was still dating that milquetoast Midwestern weirdo and Kendall had done the whole marriage and babies thing with Rava before that blew up in his face (or rather, up his nose). Even Connor was with Willa, who, regardless of how many dicks she took for money before, now seemed perfectly happy with just the one, not to mention the Brooklyn loft and $500 weekly dinners and all those brand new designer labels adorning her willowy figure with nouveau riche aplomb.
No, Roman was always the odd one out with stuff like this, though he never had an issue finding some pretty blonde thing to wrap around his arm whenever Logan became suspicious. Grace was the current one; the previous being Kate, then Sarah before her, and Eva before that. Since hitting his 30s, when he was expected (or, more accurately, warned) by Logan to “get serious,” Roman had set up a careful pattern of dating one woman for about eight months at a time, remaining footloose and fancy free for a few months, then repeating the cycle all over again. So far it served him well in staving off any real responsibility. He knew he had a bit of a clichéd “billionaire playboy” reputation with the paparazzi hivemind, but it still kept his dad off his back and stopped his siblings from fucking with him too much about it.
He liked Grace okay; she was pretty and clever and smelled good, except she was always in his space and expecting things from him. He mostly liked hanging out with Grace’s daughter, Isla, who could whip his ass in MarioKart and for whom an ice cream cone was always apology enough, whatever the problem was. He even liked playing happy family with the two of them sometimes, taking Isla to the Central Park Zoo and making her laugh with his impression of the gorillas.
Eva, Sarah, Kate, and Grace all had one thing in common (other than being blonde and makeup-ad beautiful): he’d only had sex — real, grown up, normo sex — with each of them once. Fortunately, they weren’t monogamous relationships and Roman was sure they were getting their rocks off or whatever the fuck elsewhere. He didn’t particularly mind as long as they were discreet and didn’t make a fool of him to the press or, worse, to his father. Sex for him always felt uncomfortable at best and sickeningly humiliating at worst. He’d swallowed a Viagra and done his duty the one time each with his paramours, just to prove to them (and maybe also to himself) that he could, then rolled away as quickly as possible to avoid the post-coital sweat and fluids and all that… weird clinginess that girls seemed to like. He had other ways of entertaining them when called upon to do so, often with those little top-of-the-line devices that did the job much better than he ever could.
He decided a long time ago that it was better this way. He much preferred his own hand anyway and he would never dream of breathing a single word to anyone about the fucked up fantasies that lived in his fucked up head, let alone whoever happened to be his supposedly “normal” girlfriend at the time. The extra post-gym sessions with his rotating roster of svelte, neatly muscled personal trainers didn’t hurt, either, but that was also not something he was willing to divulge outside of an airtight NDA. Besides, those little tug-n’-blow appointments really were to sex what chewing was to eating. Whenever his current girlfriend got bored of his snide jokes and his stupid fucking money and his inability to be a boyfriend in any other way but in name, the relationship would inevitably peter out and Roman would be free again.
He assumed he could keep up this charade until at least 40, at which point he might have to switch tactics. Or, with any luck, Logan might be dead by then and wouldn't be around to care, though that seemed highly unlikely. And that was fine by him, he had it figured out (enough, anyway), and he didn’t need it to be a problem any more than it had to be.
Roman Roy knew he had a lot wrong with him, so much so that he often managed to shoot the moon and come back around the other side, ending up no worse off than any other rich asshole.
But then, Gerri fucking Kellman caught him in her fucking black widow’s web with her tailored pantsuits and prissy pearls and leather kitten heels clicking up and down Waystar’s hallways and that bitchy pursing of her red, red lips and he knew his stupid little game was as good as over.
At least Gerri was still a blonde.