0:05 Welcome back to the gentlemen's edition of Careful Boys. Today we have Tim with us. What's up, Tim? We also have Joe over there doing something. He's getting dressed. Wow. Hey, your hair looks cooler now. Cooler? You had to work hard to look undone. You can't anything you could look more undone than I know. I got even more undone. I started undone. All right, let's let's have a let's have a nice little gentlemen's talk here. Oh, yeah. Daddy daddy's. Um what is What is the worst way you've ever broken up with somebody? Oh, dude. Sorry, Tracy. Aw. Shout out Tracy. This is my junior year in high school. And uh I never had a relationship past 4 months. I just felt like um if it wasn't going anywhere,
0:56 then I would just be like don't propose, just Yeah, I'm like if you're not going to propose within like 3 weeks. Put a ring on it. So, um this is my my this is the chick that I lost my virginity to. So, she it was So, it was like one bump up extra, right? V-cards? Yeah, we traded V-cards. Nice. Oh, cute. How you know that for sure? Yeah, you don't know. You actually never know. Smell test. You actually I didn't smell Did you break a hymen? Yeah. I Did you break a hymen? This hymen smells intact. You can get a certificate from her gyno. Yeah, I didn't I didn't do the the hymen maneuvers. I don't know. So, what ended up happening was um we we got together, traded V-cards, and it was going pretty good. And then, you know, sometimes like it feels like the relationship's like this, and it just goes Oh, cool. We're at a cruising altitude.
1:46 And then you're like is it going to go any more? And I didn't really feel like it was getting any more. So, I was like I called her, "Hey, babe. Happy 4 months." And she said, "Oh, happy 4 months." And then the bell Oh, sweet kisses, hearts in the air. Ooh, we And then I was like, "Hey, I actually wanted to talk to you about something." And she was like, "Aw, what?" And then I told her, "I I don't know if we should like keep going with with this. I don't think there should be month five." I don't know if like month five is like in the cards. Yes, on the 4-month anniversary. Or a monthiversary. 4-month anniversary, I broke up and then of course she starts crying and I felt bad, too, but it just felt like if I if I had empty feelings that I was going to
2:36 lead her on. You're horrible. And then so, yeah, I broke it off. And then I ended up collecting all her things from my room. Cuz in high school you What were some of the things? As a 16-year-old boy. I don't even remember, but Her Imposter mags? Her ████ Sketchers? Her Sketchers? Yeah, I don't even remember. It was ████ like, you know, like high school ████ You put it in a Put it in a box and then when she came to pick it up, which is like maybe a week or two later, she goes, "You don't I was like, "I don't." You picked up your Xbox from her? And then gave it to her and I just felt so bad. I felt so bad cuz it it was one-sided. But then I felt like it'd be worse if I played along and played along with this lie. That's Well, yeah, that's true. At least you were honest. breakup you've ever had with somebody. Okay, let's go ahead and move to Rated
3:27 PG at least. I didn't run anybody over. What the ████ What? That's PG. What? He keeps calling my breakup ████ ████ ass ████ He's like, "I ████ He didn't say all that. I stabbed a ████ in the face. He said it was cute and innocent. I I stabbed a ████ in the face. What was the worst breakup? This guy was like, "Dude, so we were on our 4-month It was the worst because of how you just felt nothing. Well, it was the worst because it was like like high five you're you're fired. Yeah. Right? You were doing such a great job. Yeah, who does that? Who does that? have to show up tomorrow. You didn't do anything wrong. And I could have waited the next day or the day before, but it was on the four month. Like who that's like ████ up. That's like waiting on Valentine's Day to divorce. Oh. Yeah, oh man, look, I was trying to break up with somebody, but then it was like, "F███, October was her birthday
4:17 and then November's Thanksgiving and then December's Christmas and then it's like New Year and then Valentine's Day." I was like, "F███." Ended up saying that ████ for like four years. Cuz it just wasn't perfect time. There's no perfect time. Cuz February to, you know, her birthday. ████ it. Yeah, it was it was it was it was it was rough. A lot of people break up before Christmas. Yeah. There's also Tracy. So they don't have to buy them a gift. Exactly. You have a Tracy, too? Was it a Tracy? No, when Savio was here, he was like, "Who's your first crush?" He's like, "Just start with a T." And I was like, "What the ████ Tracy?" Yeah. A lot of Tracy. Was everybody had a Tracy, huh? Was it a Tracy Park or a Tracy Choy? Tracy Tracy Lee. Tracy Lee? Oh, great. Now it could be anybody. My niece? No, I'm just kidding. What the hell? Was her titties all out on the plane? Did she ever try to get back with you or anything? She never tried to split.
5:07 Oh, you know what's ████ crazy? So that's high school, right? Yeah. And then and and then you know when you start getting into like early college, like the Asian club scene here? I remember going into a club in like Hollywood somewhere. Century. I forgot one of those Union Century, whatever the ████ Going upstairs and I see her. She's with her new dude. And she's like And I was like, "B████, that's ████ like five years ago, dude. I don't give a f███." feeling you then. ████ that was five years ago. You should have said that to her right then. like, "I don't give a f███." What if she like yelled across the club, "On our four month anniversary?" Yeah, she probably didn't forget it. I would have just walked back downstairs. I would have been like, "Whatever, I don't care, dude." That's so long time ago. I have an honest story that I like low-key like definitely will regret sharing here because it perpetuates like stereotypes that you guys
5:58 yeah. Stereotypes of what? Share share man. That's the term we use to describe Anthony. Nobody says ████ man here. You ████ big man. Big time big time. I was I was in a relationship one time that like in in honesty it was some of the most fun I ever had with the girl. Uh all the perks all the check boxes that you think that you like desire, but for some reason even though everything was fulfilled and satisfied like I couldn't get to a deeper place of like love. So after like 9 months You're like this? Yeah, after 9 months like even though I like wanted I can't say I straight longed for it because maybe I was just like young and just feeling this type of way about life. I had gotten out of like a other long long-term relationship. Um I just couldn't get there. She made me carrot cake. That was a huge deal in high school.
6:49 Crazy. All right. This part's about me, but thank you. That's what my dad said. "You should marry her." I was like, "What the ████ I'm 16." But go ahead. This is about Anthony, dog. Have your turn. He brings his dad into it. We got to keep it going. For carrot cake? Um so I thought the most genuinely righteous and I still I will definitely stand by this like I thought Just size six size six shoe. That's what you want to know, right? Sketchers size Sketchers size six. This bit was too good. I know I know I know. I respect it. I respect it. All this Tracy talk. you? Where were you? I want to know. I want to know. I almost said I've had better Brandy, but I haven't. Jester's court. I love you. I love you. Okay.
7:40 No more no more. Yeah. Um but uh I knew I knew the right thing to do was to not string her along. Cuz it just felt wrong as well, right? But, the sex was really good. I had to So, your dick says yes, but your heart said no. Yes. What was good about the sex, though? I'm I'm not going there. I'm not going there. Did she take care of your balls when you sucked it? No, but sometimes our mother-in-law watches this. It's not about that. I'm not going to tell you, but I swear to It's not as good as obviously right now. You know, anyways. Also, your mother-in-law shouldn't be watching it. Give me your account on Blockbuster on my phone off camera. I think at that time for me it was relative. It was relative. It was just like what I was what I needed or was looking for.
8:30 Dang, she was a relative? I didn't have enough Did I have to reveal it? Did we spoil it? It's gross. In a past relationship, that's all. I just wasn't experiencing those things, so I was like discovering. I was discovering, exploring, learning, sex, pays, the whole thing, right? Wow, she was down. I didn't know you had a Vietnamese ex. That's tight. She wasn't. Sounds like she was. Point is who she is. I'm not going to give any more details. You ████ This is why I don't want to do this ████ This is why I don't want to No, no, no, don't worry. I'll When I do the reveal, it'll be just you and kind of silent. There there is an answer. Anyway, I know, I know, I know. Um So, this is the reason why I think this is one of my worst breakups or that I did. It was a amicable
9:21 breakup. I'm still friends with this person today. Um but, like I like I wasn't out of evil or anything like that, but I feel like I was genuinely trying to be like, "Okay, well, how can I be honest in my emotional situation relationship so I don't string her along, but maybe there's still an open door to be like, "Can we like still like hook up?" Cuz that's the part that you want. I like that aspect of you. But everything else sucks. Cut cut that part. Go ahead. So, the thing is though like what I It's It's only in retrospect that I see like this is not a good thing because like obviously I still and you know, she was still into me so everything was flexible. We weren't like super super official so like she was like down. Oh, okay. But then I feel like all that really did was string it along for her. Yeah. She's like, "Maybe if I sucked it harder he would love me if I really show out."
10:11 Yeah, cuz it's a gray area. For me I feel I felt like I was cutting a certain type of like branch of like that relationship and responsibility and I was like, "Okay, cool. It's just this." Yeah. But she was she was like down because she still wanted to be something something and hold on to something and then for like It could be like purgatory for you. Yeah. Cuz it wasn't It wasn't like, "Yeah, you know what? I just want you as a ████ dude though, too. Let's go." It wasn't like that. But she was she was down and then it got to a point where we had a conversation she was like felt bad. She's like, "I feel like you know, you only want this." And I was like You're like, "That's what I asked for, dude. What the f███?" Low-key but I didn't want to say it like that, but goes, "But if I thought that if I just rode you a little bit harder you'd fall in love with me again cuz you remember." But that's when I realized how selfish like that intention was and I was like, "Okay, that's like a really not cool
11:01 thing to do if if you still want to be friends." Yeah. You know, so Cuz she was like, "Man, then I I ████ douched my butt hole for you cuz I thought if I gave you anal you'd finally love me." And what happened? Uh but point is I feel like she taught me a lot. I learned from that. I learned to do better than that and I broke it off at that moment because I like wanted to respect her as a person. Um but I do feel like I strung that along selfishly. Does she know the internal conflict specifically that you were like, "Ah, this sex is so good, though." Does she know that now? I I mean, I don't think she watches this show. Yeah, yeah. They They They don't talk to each other anymore. They're not friends anymore. But you hadn't explained that like after that that's why no. No, no, no. difficult No, I think I was just in tune with like realizing that she
11:51 couldn't just have that. Damn. So, I respectfully was like, I'm like That means your personality bad. it was healthier for the No, it wasn't. It wasn't. She's a very, very sweet person. Cuz if the sex is that good, dude, guys will make it work. It's like, I tried my best to ████ fall in love with you. Well, you know No, no, no. No, no. I feel it, though. I feel it, though, cuz as I joked earlier, I was in a long-term relationship that I ended up breaking up. I felt like Cuz the sex was good? Well, you know, sometimes someone just they don't do anything bad, and you feel bad about breaking up when like you haven't done anything crazy, but I just don't see myself with you in the long term, right? And me, especially being like 20-ish, I'm like, I don't want to ████ I don't want to break nobody's heart. So, you kind of just like ride it out. Let's wait until she does something ████ up. And they never do anything
12:41 ████ up, so you're like, "Ah, I'm wasting her time. I'm wasting my time." But we're still Cuz you're ████ up. Yeah, cuz I'm wasting her time. But it's like, you know, we're having a good time. It's just not I don't see Well, then it gets us past a certain point where you're like, "You're not I don't see you as my like my wife, you know what I'm saying?" So, why am I still here, right? We luckily we eventually had a had a big old fight where I was like, "You know what? I'm sick of this." She's like, "Me, too." Like, "Cool. We're done." Right? But Yeah, yeah. It's I just like, "Finally." Right? But to answer the question, I think same kind of similar boat to everybody. This wasn't somebody I was in a relationship with, but cuz I've only been in like two real relationships, but this girl is someone I was talking to, and same ████ I felt like, "I don't really see myself being with this this like that." And I wasn't really ready to have I was fresh out so I didn't feel like being out of a relationship not
13:31 jail. I was like I don't feel like being in another relationship and but this girl she was super pretty sex was great pretty Filipino girl and I was like but I don't want to lead her on cuz I felt her feeling it you know what I'm saying and I was like I was at I was at I was working at Foot Locker she brought me like Frappuccinos and ████ and I might I was probably young and ████ but as soon as she brought me that Frappuccino I was like she's doing too much My dad would have told you to marry her I'm like ah this is too deep she's bringing me There is that feeling right that like you're doing too much And exactly maybe that's like ████ boyish but it's like ah and she's showing too much love I'm not there so I kind of now this is me being young I was like I'm going to just not pick up the phone when she calls and I felt bad about like to this day I feel like I feel bad about the way ghosted before it was even a thing Before it was even a a term I guess so
14:21 right innovator dog And so I just kind of and she was definitely like yo what the ████ what I thought we were I thought it was good what happened Frappuccino not venti enough for you Yeah she should have got me the the grande dog what the ████ I'm a ████ dumb dude But but but to look back on it since it didn't end in a bad way we did were we were able to continue a ████ buddy situation Oh kept moving on through parts of our life but Without feelings attached But was it mutual Who cares dog That's how I should have took it Yeah but then like he's you got a heart he doesn't I wasn't I wasn't at the stage in my life to have a heart
15:12 But looking back I feel I feel I always feel bad about ignoring phone calls you know what I'm saying The Foot Locker guys didn't have a heart the Champs guys did Foot Action guys And the Payless dudes, they had a heart, they just never had a date. That's really cool. Sort of a similar thing. Yeah. Yeah. I mean, look, you know, when you when you packing heat like me and Tim are here, you know. You guys are heartbreakers. Do you Do you believe Do you actually ever believe that when when that happens afterwards and there's like a little mutual situation that it truly is mutual? You seem like maybe like you think it's always like the girl's lying. Oh, when she says yes.
16:02 You think they're lying? When she says it's mutual? Yeah, when she's like, "Yeah, I'm just in it for sex, too. It's cool." I don't think it's always just the girl. I just think it's always going to be like 51-49 at best, and then it becomes more. One person Okay, I'll rephrase it. One person's more hopeful. Okay, always? Yeah. But I do think like guys want to ████ zone and girls want a friend zone. Just say, "I don't want to ████ you no more, but I like our thing we got." guys would love to have 20 ████ zones. I've got ████ zoned by all these ████ Girl's friend zone is like the end zone, the guy's ████ zone is like the 100 yards in between, you know. Okay. It's like we we got a big zone. Yeah. I was a I was in turbulent relationships and I was a ████ dumb ass back then, like really dumb. Like um I remember breaking up with a girl because
16:54 I just got tired of her complaining, so I just did it through text. And I was like, "Hey, by the way, I think like it's done cuz I don't want to listen to you anymore." Is this through T9 text like back then? It was like I didn't even have Nokia, man. I had ████ bootleg ass I don't even know what it was. Yeah, I had Sprint and ████ But had the star or whatever ████ Yeah, the it was the Yeah, yeah, I only have three texts left. And I I didn't know that was a thing you cannot do. Like it's it's bad You got three texts? I don't know. It's still communication. Like we're talking. Yeah. So it's like I'm giving you my ████ notice. Like to me that's like a handwritten letter, but it's digital. I give you my two weeks. It's a formal email, bro. Like fair, I still think that that's actually more accurate because it's like
17:44 documentation. Yeah. It exists. You said this. Yeah, there's a there's a paper trail, you know? But I guess sincerity though. They like the in-person sincerity. Yeah, but I guess it's it's just it's just not good, right? So then like you you don't you you don't you didn't ████ properly do it. Like you didn't at least like pick up the phone and call me. Like you didn't ████ say it to my face. And I was like, "Well, ████ I don't know." And I was like, "Come get your s███." And then Get your ████ I was like, "Come get How old were you? ████ Maybe like 20 23. Okay. 22. So I was like, "Just ████ come get your ████ right?" And then And then this girl comes over
18:34 has a whole ████ thing of Rice Krispies Crispies that she makes Wow. as a parting gift. No, she comes over. She goes, "Oh, I just made it, you know, and I know you like Rice Krispies." And I'm like, "Sick." So I'm ████ eating this ████ Rice Krispies Your s███'s over there, by the way. She's ████ She collects her stuff. And then, I don't know how, but she's sucking my dick. And we're back together. Aw. Wow. it. But then after we we didn't last again. So I I probably broke up with her on But this time I didn't do it on text. I probably broke up with her on the phone or something. But Oh, that's a step up at least. But I was weak. You guys were strong. You guys were like, "Nope. I'm only going to make this a a no strings attached thing." For me, I fell right into the ████ Yeah. Hey, all it took was Rice Krispies and a ████ ████ and I'm back into the
19:24 relationship. to resist, though. Yeah, that's enough, I think, too. Honestly, you got Frappuccino and then but you guys you Anybody who comes with Rice Krispy treats and a ████ has a second chance at least. Krispies. Yeah. If if some hair would have came with my Frappuccino, I would have been like, "All right, we're back." I'm picking I'm picking up the phone. Another 4 years. You got another 4 years. You got another 4 years. You get another term. But looking back though, I was like, "Dude, that is a s█████ thing to do. You break up with someone you've been with a with the year or something with on a on a text." Like, look at I would never do that now, but at the time I'm like a ████ dumbass 22-year-old like, "Hey, man, this is a formal way of communication." And it feels easier to bear, I think, too. Oh, yeah, I guess. I wasn't even thinking about it. also think that like it all depends on
20:14 like context timing. It's like if you went on what, like three, four days with a person, do you really need to feel compelled to be like, "I need to meet you up in person, do this on a ████ formal like Three, four days, a text is straight, you know what I'm saying? Or or if the context in which you guys met up it's like you met up you at a party, you hooked up, it wasn't built on some friendship. You were like just You know, I think context is is It wasn't a Those are just not even relationships. But you know what I mean? Like Yeah. But maybe maybe it lasts a little bit and like every single time you're getting together you almost like pretend like you're dating so that you could just hook up. so ████ if after a hookup you're like, "Can we meet up?" And you're just like, "It's not going to work." That's hilarious. That would be so good. Like I haven't even seen you during the day. She doesn't even ████ care. They're just like, "You know, this is She's like, "I'm sleeping with other
21:05 people right now." She's like, "Dude, real talk." We were never together. goes, "No, we were." Can't be She got It's a power struggle. Mhm. Like, who's being a guy that's never broken up like that? Who's do you think was the worst out of all of them? You didn't even say your story. Honestly, probably Bart's. Probably Bart's is the worst. What is he talking about? You think Bart's is the worst? I don't even remember Bart's. To the girl To the girl was the worst. Really? Like, she took it the hardest, so it's the worst. That's true. Cuz it's like he's doing it on a celebration day. Yeah, yeah, yeah. That was like breaking up with someone on the wedding day. Yeah. And she held And she held it for 5 years until the club night. At her age, she held on to that. True. That's like Taiwan becoming China again during Lunar New Year. There were still benefits, you know? You had There were still hooking up with you guys over here. She had She was left with nothing. She was left with nothing. Yeah, but he didn't do it on a holiday. He was sleazing and pleasing.
21:56 He didn't ████ do it on a holiday. Key word Key word, Bart, pleasing. This poor lady Poor Tracy, dude, was stuck. I don't I don't think I've ever heard Bart say a rhyme before. That was good. He's sleazing. He's pleasing. The real deal and son of a gun. Wait, that's a lie. I've heard you rap.
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