Is he orchestrating a threeway?

My (20F) FWB (32F) is great. We have the best sex and conversations, but the caveat is that we’re both super busy (he is a ceo and I’m also on the founding team of a startup), so we’ve actually only hung out three times over the past few months because our schedules hardly align. Our dates have been high quality (really exquisite meals/places) and we usually spend the whole night together (say 7pm-1am), we just get along so well (he says I remind him of himself) and time flies by. I’ve also been introduced to some of his friends after he took me to a housewarming soirée, and he told me they wanted to see me again. I like him and I don’t expect this to go past fun/casual dating, but it’s clear that we prefer each other’s company enough to keep trying to meet.

A few days back he texted that a female friend from out of town was visiting him, then he asked if I wanted to go on a “date” with the two of them (he used “me and her” when asking, not “us”). Prior to this we’d been trying to schedule a double date between us and our friends, but that fell through. He is from the Mediterranean so it could easily be a friend from home, and certain words definitely have a different meaning for him than they do native English-speakers, but I still can’t fathom what it would mean to hang out with him and a woman who 1) he doesn’t normally see and 2) is in the area just for his sake, if it isn’t to try to somehow get us to all hook up. But am I being immature by assuming this, given that I’m not his age? What do you guys think? Is there a possibility that he just wants me to meet his friend (maybe I’m being vetted?), or is there clearly an ulterior motive?

Submitted November 24, 2021 at 12:09AM

My (20F) FWB (32F) is great. We have the best sex and conversations, but the caveat is that we’re both super busy (he is a ceo and I’m also on the founding team of a startup), so we’ve actually only hung out three times over the past few months because our schedules hardly align. Our dates have been high quality (really exquisite meals/places) and we usually spend the whole night together (say 7pm-1am), we just get along so well (he says I remind him of himself) and time flies by. I’ve also been introduced to some of his friends after he took me to a housewarming soirée, and he told me they wanted to see me again. I like him and I don’t expect this to go past fun/casual dating, but it’s clear that we prefer each other’s company enough to keep trying to meet.A few days back he texted that a female friend from out of town was visiting him, then he asked if I wanted to go on a “date” with the two of them (he used “me and her” when asking, not “us”). Prior to this we’d been trying to schedule a double date between us and our friends, but that fell through. He is from the Mediterranean so it could easily be a friend from home, and certain words definitely have a different meaning for him than they do native English-speakers, but I still can’t fathom what it would mean to hang out with him and a woman who 1) he doesn’t normally see and 2) is in the area just for his sake, if it isn’t to try to somehow get us to all hook up. But am I being immature by assuming this, given that I’m not his age? What do you guys think? Is there a possibility that he just wants me to meet his friend (maybe I’m being vetted?), or is there clearly an ulterior motive?