After his second divorce, things finally clicked for Jay - love wasn’t in his cards, and that was okay.
That didn’t mean love didn’t exist. People still fell in love every day, they still got married, things still lasted. People went on dates to coffee shops, and cafes, and did the dinner and a movie cliché, with both right and wrong people. There was just no right person out there for him, and there probably never had been, no matter how much he’d let himself believe there might be, that he’d found that right person.
But everyone got tired of swimming through an entire ocean just to find that right fish amongst millions. And he could make a decent paycheck by swimming through all of those options for them, or at least doing some of the research.
Will and Connor met outside of Jay’s matchmaking skills, the old fashioned way. They’d gone from antagonistic coworkers, to reluctant friends, to some hand wavy relationship involving sex and pretending feelings weren’t involved, to a wedding. They’d gone were some of the lucky ones, the ones who found love instead of just someone who was willing to tolerate them for a few years, and he was happy for them.
Besides. Weddings made for good networking opportunities.
Gregory had spent his entire life with everything planned out, each stepping stone nearly placed in front of him by his mother right up to the door to his future - taking over the family business, getting married, producing heirs… It had sounded so easy when he was a kid, wanting nothing more than to make his parents proud, and it took a lot longer than it should have for him to realize how far he’d started to stray from his planned out path.
He was still in line to take over the company, that wasn’t going to change, and thanks to his favorite Supreme Court ruling - and really, one of the only remotely good ones - he could still get married and have a family. But his parents had gotten married in their twenties and still barely managed to have one child before thirty crept in, that threatening shadow of age that so many people hated. He was getting far closer to forty than twenty, edging into the later half of those dreaded thirties, and it was getting increasingly clear that his mother’s pride, at the very least, had rapidly dwindled away the moment he decided to tell her he liked men.
If he could claw his way back onto the path he was supposed to be on, maybe that could change. Maybe he wouldn’t be subtly ignored by his own mother at every event if he had ring on his finger and a husband on his arm. And his best friend’s new brother-in-law was a matchmaker, which meant he had the best chance at changing his life that he could ever hope to find.
Love didn’t have to factor into it. Marriage for people in his tax bracket was as much a business contract as signing a check. Just because Connor was able to find someone he actually liked didn’t mean that changed things for the rest of them.