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11 Guys Share The Stupidest Dating Risks They've Ever Taken

Love is a gamble
by Chandra Pepino | Feb 3, 2018
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We would do anything for love—and, to Meat Loaf’s retroactive dismay, we’ll even do that. Dating can be volatile and upsetting, especially after realizing that the things we’d sacrifice for one person aren’t things they’d even consider doing for us in return. But we’ll drink a beer and laugh about it. A story for our grandkids, right? Here, 11 men (very regretfully) spill the beans.

“I impulsively left my girlfriend of three years because I met someone else. We were great for a while until I found out she was a compulsive liar who would fork bills out of my wallet while I was asleep. My ex went on to get engaged to this tall Swedish dude. Reading the Facebook post about her engagement was when I realized I made the biggest mistake of my life.” — Josh, 26

“When I was in college, I had no idea how to commute. A girl I had a crush on since high school who went to UP wanted to watch a movie at Cine Adarna. After asking her for directions I commuted to UP. I stayed in UP with her until late night. I didn't see any more jeeps so I had to walk home in the dark under the rain.” — Rucha, 24

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“We only got to date for about a year before she migrated to the States with her family. I decided I would try to flunk all my classes, armed with the messed-up logic that my own family would send me to the States after seeing how much of a wreck I was without her. But then I realized, teka lang, hindi kami mayaman!” — Mik, 29

“I courted this girl back in college (and failed). She eventually ended up with my best friend. I had a small inkling that my best friend was actually gay and was using her as a ‘beard,’ but I never told her that because she would think I was jealous and trying to sabotage her relationship. I should have fought harder for her, because in the end, I was right about my best friend. He found a boyfriend, while she nursed a broken heart. Her pride was too bruised to even consider dating me at that point.” — Carlo, 24

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“I applied to grad school in Massachusetts because the girl I was in love with was studying there. I spent P13,000 to take the GRE (Graduate Record Examination), but I was rejected by every single university that I applied to. Also, she met someone else. Fuck me, right?” — Jim, 23


“I bought her a concert ticket to the Justin Bieber Purpose Tour last year. You know, the one that got CANCELLED. She said she would refund her ticket, but she never gave me back the cash. I’m the idiot for buying them for her in the first place. We had only known each other two months.” — Aldrin, 26

“Sharing my ATM PIN with my girlfriend. She was supposed to hold on to my debit card for emergencies only. Yeah, sure, if you could call a Forever 21 shopping spree an emergency.” — Ed, 24

“Moving in with a girl without doing a trial run first. We went for it right away. She was a total slob, we argued about little things every day, and it just killed every hope I had that the relationship would work out. I mean, I guess I’m glad I found out early.” — Seb, 25

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“Staying with someone who didn’t understand my depression. In her defense, she came from a pretty fucked-up family, so she was ill-equipped to handle someone like me. She would put me down every chance she got, complain that I was failing my classes and ‘not being the man she thought I was,’ and kept nagging me to open up to her even when I didn’t have the mental energy to do so. I was afraid if I broke up with her that no one else would love me. I should have realize my worth sooner and left.” — Jose, 23

“Hooking up with someone else’s girlfriend. His friends came after me like vultures and posted the screenshots of my dirty conversations with the girl all over social media. Including the nudes we exchanged. Our entire (small) college talked about it for weeks. Worst thing I’ve ever done.” — JP, 20

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“I regret ruining my relationship with my parents because of the girlfriend I had in high school. They caught me in a Skype call with her—she was naked in front of her webcam, dancing for me. My parents forbade me from seeing her, but of course, I rebelled. Fast forward to when she broke my heart into a thousand pieces, which caused me to rebel even more. Alcohol, drugs, the whole thing. That was almost 8 years ago, but it still hasn’t been the same with me and my parents.” — John, 25

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