My older brother’s best friend is cute, nerdy, and apparently capable of losing access to his entire vocabulary when a pretty woman appears. I’ve known him for about six years, since high school. We’re adults now, but his friends still discuss his dating life with the commitment of a committee that has never successfully completed a project.
He’s never been on a date. He’s talked to women, but those conversations haven’t lasted longer than a week. According to the recurring updates, he’d like to have his first sexual experience and hasn’t had much luck.
My brother and their friends offer advice. He gets nervous. Things go nowhere. Then there is more advice. The supply seems inexhaustible, which is impressive given the results.
Meanwhile, I’m attracted to him.
This makes listening to the updates slightly awkward. They’re discussing where he might find someone interested, and I’m right here, already interested, wondering whether saying so would create a situation nobody needs.
I’ve thought about him that way before, and I’ve caught him checking me out a few times. That could mean there’s some attraction on his side. It could also mean I’ve noticed a few glances and supplied an ambitious interpretation. We haven’t actually talked about it.
I don’t usually have casual hookups, but I enjoy sex, and the idea of being with him sounds fun. The complication is that he’s my brother’s best friend. He’s someone I’ve known for years, with a place in my life that existed well before this particular thought showed up.
And ‘helping him out’ sounds much simpler in my head than it would coming out of my mouth. I’m interested in him; I don’t want to make him feel like the latest person has arrived to discuss his lack of experience.
I haven’t offered anything. He hasn’t asked me. At the moment, this is a possibility I’m considering while everyone else continues providing unsolicited coaching. Is there a subtle way to let him know I’m interested, or is this one conversation I should leave unstarted?
