Tom and I have hooked up a couple times in different situations, but the last time got awkward and he started dating someone, Tom is also a bit older than me.
It had been a few months since we’d even talked at work, and one day a few people were drinking at the bar near our office, and Tom was there. We started talking, apparently he’d met this girl, they’d gotten engaged, and broke it off all in a few months. Felt bad for him cause he’s a genuinely nice guy.