TLDR
I'm a 26M. I've never had a truly confident hookup phase in my life. Wondering if I'm missing out and if I will regret not pursuing it. Currently in my 2nd long-term relationship with a great girl, though.
Hoping I can get some stories from guys who have broken off a relationship with a good girl to pursue an unlived hook-up phase and how they feel now. What happened? Are you happy? Do you regret it? I just want to know your story.
BACKSTORY:
I didn't even kiss a girl until college. Had 3 hookups with girls who initiated with me from 18-20 years old. Those were very infrequent because I was insecure and needy as fuck. I went my entire sophomore year of college alone and jacking off for example.
COVID happens, I move back home with my parents at 21 years old. I was craving having a steady girlfriend and actually matched with a girl on Tinder in 2020. We dated for 2 years.
In January 2023 I broke things off because our lives were going in different directions. She wanted to settle down, buy a house at 23 years old, I wanted to take advantage of my youth, travel, explore the world, develop social confidence.
I broke things off with her after like 6 months of pondering it and took advantage of having a remote job. I traveled around, lived in different countries, pushed myself to approach girls, make new friends, and was getting more and more confident as the months went by.
I still wasn't really sure who I was though and what I valued. What type of girls I liked or what type of girls liked me. Like I would go to nightclubs even though I was NOT (and am not) a nightclub type of guy.
But I was trying to explore what the world had to offer and say yes to as much as I could.
I was finding myself, approaching women, had like 5 hookups in the span of 10 months or so. Nothing crazy but more than I ever had before.
October 2023 I'm digital nomading in a Latin American country and met my current girlfriend. I got to know her at the gym. She was (and is) very cute and I really liked her personality. At the time I was also feeling ready to get to know a girl deeply again, being 10 months removed from my last relationship.
But in retrospect, I also needed some validation that there was another girl out there whom I could develop a strong relationship with.
CURRENT SITUATION:
Me and this girl live together in the Latin American country. I’m working remotely. Living my life down here. Taking care of myself. Working out. Working on building an online business. Our relationship is really good honestly. We get along very well. Our personalities click more than me and my last gf. Sex life between us is good. She’s very generous in the bedroom iykwim. She's funny. Attractive. Smart. Very socially and emotionally intelligent.
But… god dammit… it’s Jan 2026. For the last year or so honestly I’ve been having this itch of being single again. Traveling the world again. I’m craving the thrill of approaching and dating new girls again. Confidently. As a 27 y/o man who’s grounded in himself this time, not as a 23 y/o boy trying to find himself like my first single approaching chapter in 2023.
I’ll be honest man. I get sexually triggered constantly by other women. Constantly looking at other women. Just watched Zootopia 2 and the god damn bunny rabbit had me– alright I’ll chill LOL. But you get the point.
Also having on and off porn phases. I swear it's easier to avoid watching porn when you're single than when you're in a relationship.
I don’t want to be hard on myself. I’m a 26 year old guy. It’s normal for me to be horny and look at other women. But I’m just feeling like I still have this other single phase in me. But when I think about ending things with my gf, it’s really sad obviously. We’re not just in a relationship, we're best friends.
I’d probably get over a break up but just don’t know if it’s worth it? This unlived chapter of my life.
MY DREAM
I just feel like I haven’t fully expressed my masculinity within dating dynamics. Leading. Teasing. Approaching confidently. Being grounded in who I am. It's this thing I know I can do if I had the opportunity, and I do really want to experience it, honestly.
I have this 5-year vision for how my life goes. I'm 26 now, soon to be 27. For the next few years, I'm single. Traveling. Approaching, dating, having the best sexual experiences of my life. Building up my online business that I'm currently working on. Making new friends. Playing sports, socializing. Living a full life.
Then in like 3-5 years from now I look into being in a relationship again. As a man who has sewn his oats and ready to be in a "settled" down thing. In general, I feel like settling down is something I'd rather do when I'm around 35 years old (+/- a couple years) rather than in my 20s when I feel like I haven't had enough life experience.
THE OBSTACLES
The reason I haven't broken things off is mostly due to fear of not meeting a girl as great as my current girlfriend when I'm ready for a serious thing again. Also worried that this single life won't be as fun as I thought and I won't be fulfilled, leading to overwhelming regret.
I know this is a tale as old as time. Man in relationship wants to be single lol. Nothing new.
But that’s my situation. Those are my thoughts. Would love to know HONEST stories and thoughts from guys who have experienced a similar situation. Was it worth it? Are you happy?
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