Ryan Jay Keeps Falling For His Friends

Proxy with Yowei Shaw

Ryan Jay joins Proxy host Yowei Shaw to discuss a recurring pattern in his life: developing romantic feelings for female friends after months of platonic

Key takeaways

• Ryan Jay confesses he repeatedly falls for female friends after months of platonic closeness, often resulting in the friendships drifting apart or ending entirely.
• Psychologist Andrew Smiler explains that American culture restricts men's emotional expression to romantic relationships, causing them to naturally attach romantic intent to deep platonic bonds.

Main topics

• Platonic vs romantic friendship boundaries
• Masculinity and male emotional expression

Notable quotes

"I feel like every single woman on earth that has had a friend of the opposite sex has had this happen to them."

Conclusion

The episode provides listeners with actionable psychological strategies to navigate the blurry line

Transcript preview

Speaker 2 (0:00) I'm Elizabeth Day, creator and host of How to Fail, where we hear from people like this. Speaker 1 (0:04) For Schitt's Creek, for example, if I had a partner going into that experience, I certainly would not have had that partner coming out of that experience. Speaker 3 (0:12) It's a talent to be a mom. You know, it's a skill. And even... We actually seen Miranda fail at a lot of things that was the best thing that could have happened to her. That's How Speaker 2 (0:25) to Fail. Find it wherever Speaker 3 (0:27) you're listening to this. Speaker 3 (0:36) Back in February, I got on a video call with a 27-year-old Filipino-American guy to talk about his problems with women. I didn't know what to expect. Do you want to just use your first name or do you want to use a pseudonym? I Speaker 1 (0:50) think I'm fine with my first name. Speaker 3 (0:51) Okay, so Ryan. We'll go with Ryan. Or Speaker 1 (0:54) Ryan J. Both are fine. I respond to anything. Ryan, Ryan J. David. I called up Daryl once. Speaker 3 (1:00) Oh my gosh, Daryl. How come Daryl? Speaker 1 (1:03) Someone misremembered my name at work and I just used it for three years. Speaker 3 (1:07) No, you're kidding me. Speaker 1 (1:09) Most of the staff called me Daryl. One of my closest co-workers called me Daryl. One time I brought over a significant other and then I said, hey, Daryl. And then she said, who's Daryl? Speaker 3 (1:20) What'd you say? Speaker 1 (1:21) I'm Daryl. Speaker 3 (1:26) I've never met someone like Ryan Jay, not Daryl, for lots of reasons, including the fact that he's the first straight guy I've talked to who wants help not getting Speaker 1 (1:37) the girl. I came specifically to the podcast not because I'm looking for dating advice, but I'm looking for friendship advice. Speaker 3 (1:44) Ryan Jay tells me he started falling for his best friends a few years ago. He'd gotten out of an eight-year relationship, was enjoying being single. And he started getting close to someone he met through mutuals, playing video games together, talking on Discord for hours. I Speaker 1 (2:02) remember this one specific night, we just kept talking and talking about life, about the inconsistency of humans being both like the most selfless and selfish beings to ever exist. And at some point, I noticed that the sun was coming up. And I said, oh my God, we talked all day until morning. And then they said, we'd like to talk some more. And I said, yeah. And we kept talking. Speaker 3 (2:24) Well, sounds... Kind of romantic? Speaker 1 (2:27) Not really. I feel like I do that with friends that identify as male also. Speaker 3 (2:32) Well, you know, friendship can be romantic, right? Speaker 1 (2:35) Can it? Speaker 3 (2:36) He didn't see this friend that way at all. Until suddenly, after months of being besties, he did. And he couldn't stop thinking about them. Their inside jokes, treats he wanted to get them. He started seeing their favorite color everywhere. Royal purple. Speaker 1 (2:53) Maybe you can call me cliche, but... I remember this specific moment where I made like such a... silly offhand comment and they had this laugh to them. And the way they laughed, it reminded me of ringing bells in sunlight. And I thought to myself, I'd like to make her laugh like that every day. Speaker 3 (3:14) He tried to fight the feelings. He really did. He wasn't interested in dating at the time and he really didn't want to risk losing the friendship. But after a month, he couldn't hold it in any longer. He told his friend how he felt. That he was into them. That he could see a future together. Speaker 1 (3:33) After I said it, they were very, I want to say... Not cold, but... Speaker 1 (3:44) Off-put. Speaker 3 (3:45) How could you tell? Speaker 1 (3:47) Probably the, oh. Speaker 3 (3:49) Not the, oh. And Speaker 1 (3:53) at that moment, I knew that it was probably a no. Speaker 3 (3:56) Yeah. Speaker 1 (3:57) But they said, oh, I'll think about it. And then over the coming days, over the coming weeks, I felt the drifting. But we were still close. We still talked until one day we weren't. Speaker 3 (4:06) Did you ever communicate that if they don't feel the same way, that's fine? Like you want to stay friends? Speaker 1 (4:13) I did, yes. I explained to them that having them in my life was more important than anything else. Speaker 3 (4:21) This has now happened to Ryan J. two more times. He'll get close to a new friend over several months. It's just platonic. Then at a certain point, he catches feelings and then discloses those feelings. Then they drift apart. Are you trying to date these people from the beginning? Are they people like you already had crushes on? Speaker 1 (4:41) Oh, no, no, no, no. I feel like it would be disingenuous of me to want to attempt a platonic relationship with a person. just to try to get a chance at a romantic relationship. Speaker 3 (4:54) I Speaker 1 (4:54) assure you the closeness and the connection was genuine. It's just at some point I develop feelings and they don't. Speaker 3 (5:03) Why not say nothing? Speaker 1 (5:07) Have you ever shook a bottle of soda and then not take the cap off? Speaker 3 (5:13) Mm-hmm. Mm-hmm. The Speaker 1 (5:15) pressure of the carbonation, like pressing on those plastic walls, knowing that if you slightly open that cap, it would fly across and put a hole in the roof. Speaker 3 (5:28) Ryan J. wishes he could screw the cap back on these feelings, that these friendships never got shaken up in the first place. He misses his buddies. And now he's afraid of getting close to anyone new for fear of falling in love with them. Speaker 1 (5:44) I've never wanted to be that guy. I feel like every single woman on earth that has had a friend of the opposite sex has had this happen to them. Where you feel like you're having a good photonic relationship with someone. And then they get that dreaded text that says like, hey, I need to tell you something. And I can imagine that pit fall in the stomach. knowing, oh God, not again. Speaker 3 (6:09) Why do you think this keeps happening? Speaker 1 (6:14) Well, at first I thought it was... A desperation from a lack of intimacy. Speaker 3 (6:21) Yeah. Speaker 1 (6:22) But I feel incredibly fulfilled with the great friends I have, with the freedom of being an individual and single and being able to do what I want with my own time. I enjoy it. I like being alone. Speaker 3 (6:36) Okay. Speaker 1 (6:36) So I don't know why it keeps happening. Speaker 3 (6:39) I asked Ryan Jay if maybe he's sexually frustrated, and he swears these crushes aren't driven by physical lust. And it's not like he's attracted to all his female friends. It's only when he gets extremely close that he starts crushing. And he says he's looked into demisexuality, but that doesn't fit him either. Speaker 1 (6:59) I would like to find a way to keep it platonic and without developing a romantic attraction. Speaker 3 (7:06) And this is why he came to us. Speaker 3 (7:10) Ryan Jay hasn't found any good answers on the internet. Just a bunch of red pill, alpha male men going their own way crap. Telling him to get rich, buff, and a Lamborghini. Or worse, pages and pages of pickup artist bro tips for emotional manipulation. Speaker 1 (7:28) Just talk to her like two texts and then don't answer her for maybe three days and she'll be hooked on you. That doesn't sound like closeness. That just sounds like you're carrot sticking a horse. Speaker 1 (7:40) I want to live fully and wholly, and that includes loving the people around me. And I don't want it to develop into something awkward and strange. Speaker 3 (7:53) After the break, a proxy who gets it. Speaker 3 (8:01) Do you like stories about liars, scoundrels, and ne'er-do-wells? Of course you do. People who break the rules make for fascinating characters. That's why you should check out the latest season of our fellow Radiotopia show, Only If You Get Caught, a podcast dedicated to taking a closer look at cheating scandals and uncovering what they teach us about the world. This season, they're covering things like, what's the story of the infamous book that teaches us about how publishing really works? Why do people keep cheating at marathons despite getting nothing out of it? And why was Sam Bankman Freed doing all that? Only If You Get Caught is hosted by Patrick Redford and produced by Alex Sujong-Loughlin from Defector Media. Their releasing episodes all fall wherever you get your podcasts, including YouTube. Speaker 1 (8:52) Good morning. Well, afternoon. Speaker 3 (8:55) Hi. It's so good to see you again. Have you fallen for any other women friends? Speaker 1 (9:00) No, no, I have not. Speaker 3 (9:02) The day of the proxy conversation, Ryan J. tells me he's forbid himself from chasing anything romantic this year. He has met a few new women friends, but he's keeping his emotional distance just to be safe. Speaker 1 (9:16) I want to be able to have a good, deep, intimate friendship with a woman. without. falling for her, obviously, right? And the solution right now is just don't do that, which doesn't sit right with me. But I think that understanding my own limitations is important for me right now. Is he here? Speaker 3 (9:41) Yeah. The proxy's here. Ooh. Speaker 3 (9:46) Looking for Ryan J's proxy, there was this funny contradiction. Ryan J's problem was not niche at all. A cis straight guy falling in love with his female friends happens all the time. I've seen and experienced it myself. On the other hand, it's such a common situation that people don't really comment on it. We didn't find any memoirs, support groups, viral essays. But luckily, there is Andrew. Speaker 3 (10:19) Ready for me to let him in? Speaker 1 (10:21) Okay. Speaker 1 (10:24) Hi. Oh, hello, sir. Speaker 3 (10:26) Andrew Smiler is a psychologist who specializes in working with men. He feels an obligation. Back in 2000, Andrew was getting his PhD in developmental psychology when he took a psychology of gender course. Speaker 2 (10:40) And we spent 14 weeks on women and one week on men. And I thought, this isn't quite right. Speaker 3 (10:47) Andrew went on to study and write about boys and men for decades and eventually returned to clinical work. And he says he's worked with several guys like Ryan Jay. Though, of course, this isn't therapy. This is just a proxy conversation. Ryan Jay's a little nervous. Speaker 2 (11:03) It's Speaker 3 (11:04) all Speaker 2 (11:04) right. We can talk about darts if you like, because I can see that dartboard behind your head. Speaker 1 (11:08) I assure you, I'm very mediocre at darts. Speaker 3 (11:11) Ryan Jay told Andrew how he wants to stop falling for his best friends. I'm Speaker 1 (11:14) not trying to get the girl anymore. Speaker 3 (11:17) And lately, he's been trying a new tactic, what feels to me like a pretty extreme last-ditch measure. Speaker 1 (11:23) I imagine everyone as goo. Speaker 1 (11:27) Goo? Yeah, goo. You know, just gray, gelatinous cartilage of nothingness. So I talk about our jobs. I