I (F30) live in a big city and play a sport at a competitive level. About a year ago I joined a social team through a very tangential reference and met my now-friend (M23) who we’ll call Caleb.
I don’t really know how to write this post beyond that. Caleb and I really hit it off in terms of the sport initially, going on fairly quickly to play in and win a number of tournaments together outside of this more social team where we met because we both play at a more advanced level, but beyond that I wasn’t seeing him much. I am a fairly reserved person and he is as well; I don’t really date much which is a huge part of why this whole situation makes me so anxious I think, and my understanding is that he is similar, going on occasional dates but not using the apps or anything.
As we got to know each other, it’s become so clear that we’ve got a lot in common. Similar senses of humor, really lively debates, trivia nerds, voracious readers; I would say late Fall 2023 is when I realized I’d definitely developed a crush on him. He’s really difficult to read, again fairly introverted, but I started inviting him to social things beyond our sport and he comes to almost everything I invite him to. Despite being introverted though, he is kind of a person who is down for anything, so it’s been tough to tell whether he’s coming to my stuff because he wants to spend time with me or just because he vibes. That being said, I often feel like there’s real chemistry between us, and don’t think I’m entirely imagining it because I’ve had at least five people approach me separately to ask whether we are hooking up or there’s anything going on between us.
Long story short though, I’ve been too chickenshit to say or do anything about it. I’m definitely at the point on my end of having a hopeless crush on him, I think he’s really smart, perceptive, kind, funny, attractive, etc. but I think the main thing holding me back beyond my inherent shyness when it comes to guys and dating is the age difference. I don’t want to overstep something and make him uncomfortable if I’ve misread anything.
For a little more context, we’ve got another friend (F33) who apparently developed an interest in him about 6 months before I joined the team. Now, she is very different from me in a lot of ways; she’s in a well-established polyamorous relationship, is extremely confident and blunt and outgoing in pursuing her sexual interests. She told me later (once I admitted to her that I had a crush on Caleb after she directly asked me whether that was the case) that she’d asked him out very directly in Spring 2023 and he very kindly but emphatically turned her down. She chalks this up though to his personality and values, recognizing that she may not be his cup of tea in that respect, and noted that he was really fantastic in handling her advance; they are still good friends.
On the other hand, a teammate (M33) of ours tried to set him up with a friend from college (F32) and Caleb was open to that. He took her number, apparently texted her a while, but she ended up ghosting him (he noted this happened after she found out his age).
I know there might be questions about why he seems to be the youngest person in any of these scenarios and all I can say is that’s true but also he doesn’t “seem” 23 if that makes sense. I recognize there’s nothing more cliche or honestly gross than saying he’s “really mature” or seems like an “old soul,” but that’s the best I can do. In the context of the sport where we met, there’s definitely a full range; the oldest person on our team is 41 and Caleb is the youngest at 23. I’ll also say I’ve become loose friends with his roommate (M23) as well; he doesn’t play our sport but joins at activities sometimes and is also a really good guy, though not someone I’d have any romantic interest in. Just to say Caleb’s not always alone in his age range, and that I think he generally just is a good person who makes friends with good people.
I guess I’m just posting here to ask for any advice or insight anyone’s got. In a dream world I would really prefer to get a clear advance from him first, but I think both the age difference and his fairly reserved personality make this a non-starter at this point. He has also definitely heard me talk about the fact that I don’t date much and I worry that might have either put him off or discouraged him from interpreting any interest from me if that makes sense. If anything is going to happen between us, I think I would have to make the first move, but I’m terrified of doubling down as the second “older woman” on the team to make an advance, and/or to impact the dynamic we have as friends and playing this sport competitively together.
This is my first ever post to Reddit so kindness would be hugely appreciated, as well as any advice anyone can offer. Thanks everyone!
Tl;dr I have developed a huge crush on my teammate who is younger and we are both fun but reserved people who don’t date much so I don’t know what to do about it without risking the friendship or maybe my pride