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Monday, October 6, 2025
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GIRL ASKED BOYFRIEND IF SHE CAN FLIRT WITH OTHER MEN FOR DRINKS

My [28M] GF [28F] Texted Me While Out with Friends Asking If She Could Flirt with Guys for Free Drinks – Am I Overreacting?

Hey everyone, I could really use some outside perspective on this because my head’s spinning a bit right now. My girlfriend and I have been officially dating for about a year now, but our history goes way back – we’ve had these on-and-off flings for around five years total. It’s been a rollercoaster, but we’ve always seemed to find our way back to each other, and things have felt more stable lately. We just moved in together a couple of months ago, which has been exciting but also a big step, you know? We’re both 28, trying to build something real after all that back-and-forth.

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Background

A little background on me: I’ve got some trust issues from past relationships. I’ve been cheated on twice before – once in college by an ex who I thought was “the one,” and again a few years later with someone I was really invested in. It sucked, and it left me pretty guarded. My girlfriend knows all about this; we’ve talked about it openly, especially when things got serious between us. She’s always been reassuring, saying she gets why I’m sensitive about certain things and that she’d never do anything to hurt me like that.

Anyway, tonight she went out with this new friend of hers – some woman she met through work recently. They were hitting up a few bars downtown, nothing out of the ordinary for a Friday night. I was at home chilling, watching a game and not thinking much of it. Then, out of nowhere, I get this text from her around 10 PM: “Hey babe, the drinks are expensive here lol. Would it be okay if I flirted a little with some guys to get free ones? Promise it’s just for fun.”

What The…

I stared at my phone for like a solid minute, feeling my stomach drop. Flirt for drinks? Like, what? It immediately triggered all those old insecurities – the cheating, the betrayal, the fear of being played. We’ve never really had an agreement about stuff like this; our relationship is pretty monogamous, and we’ve joked around about bar scenes before, but this felt different. It wasn’t just hypothetical; she was out there, asking permission in the moment.

I texted back pretty quickly, trying to keep my cool but also testing the waters: “Wait, seriously? If that’s cool, can I do the same next time I’m out? Or is there a specific guy there you want to flirt with?” I figured it’d highlight the double standard or at least get her to clarify what she meant.

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She didn’t respond to the first part at all – just ignored it like it wasn’t even there – and replied, “No, I don’t want to flirt with anyone specific. Just thought it’d be easier than paying full price.” We went back and forth a little more, but it felt tense. I told her it made me uncomfortable, especially given my history, and she said she was sorry if it came off wrong, that she was just tipsy and joking around. But honestly, it didn’t feel like a joke to me. She ended up heading home early after that, and when she got back, we talked a bit in person. She apologized again, said she didn’t mean to upset me, and that she’d never actually cross any lines. We cuddled up and watched something on TV to smooth things over, but I’m still stewing on it.

Look, I get that we’re adults, and going out shouldn’t mean we can’t have fun or that every interaction is a red flag. We’ve just moved in together, and I don’t want to blow this up into a huge fight or make mountains out of molehills just because of my baggage. Our relationship has survived way worse than a weird text, and she’s generally been great about respecting my boundaries. But this one hit a nerve hard. Is it reasonable for me to be this upset, or am I overreacting and letting my past cloud things? How would you handle a situation like this? Any advice appreciated ⬤

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