AITAH For Roasting My Date & Her Friend For Bringing Her Friend To Our First Date, And Expecting Me To Pay?

The restaurant’s warm glow promised romance, but Jake’s gut twisted as his Bumble match, Lily, strolled in with a plus-one. At 27, he’d vibed with her off-app, even agreeing to her friend tagging along for safety—anxiety’s no joke, he figured. But when the friend, decked out and demanding he foot her bill too, turned their date into a trio, Jake’s patience snapped. His sharp quip about swords and threesomes cleared the table fast.

Readers might feel that dating sting, picturing a setup gone sour under clinking glasses. Jake’s blunt roast—public, biting—left him wondering if he burned bridges too hard. Was he right to call out a bait-and-switch, or did his jab cut too deep? This tale spins a raw riff on modern dates and dollar signs—let’s dig in.

‘AITAH For Roasting My Date & Her Friend For Bringing Her Friend To Our First Date, And Expecting Me To Pay?’

I (m27) had met this girl (23f) on Bumble a few weeks ago. Got around to talking off-app for a while. We really seemed to hit it off, but she confided in me that she suffers from anxiety and has had some bad experiences with some exes who truly sounded awful, important for later.

We get around to scheduling a dinner date at a restaraunt I really love, and she asked me if her friend could come as well to make her feel safe. I was a little surprised at first, and thought it might make the date a bit awkward, honestly. but I told her that thatd be fine if it helps her feel comfortable.

I'd heard about this kind of thing before anyways so I figure it's some new thing women are doing to sus out bad dudes, so I understand where she's coming from. The problem arises once we actually get to the date, her friend is just as dressed up as she is,

and they both seemed excited, so I asked the friend directly what her plans were for this, if she planned to just hang out, if she was ordering for herself or what. The friend starts getting a bit aggressive with me almost right off the bat, telling me that she's basically a part of the date too,

and expected me to pay for everyone (I had already offered to pay for me and the girl I was taking on the date, but her friends bill wasn't ever mentioned) Now in my head, I figure this would've been something where the friend was like, there just in case, but I didn't figure this would mean they'd actually be participating in the date?

I straight up tell them that this isn't cool and that I wouldn't have agreed to this, and told the friend,

Part of me feels like I was correct in pointing out the weirdness and awkwardness this whole situation put me in, and rejecting the date altogether,, but I can't help but feel like I went a bit too far getting at them like that in a public place, like I should have just left without a fuss, or gone along with it and just break it off more nicely afterwards.. AITAH?

First dates are nerve-wracking enough without uninvited guests, and Jake’s caught in a classic conundrum. Lily’s anxiety plea for a friend’s presence sounds fair—safety’s key in 2025’s dating scene—but her friend’s entitled demand for a free meal flips it to shady. Jake’s agreement didn’t sign him up for a group tab, and his pushback, though brash, called out a boundary breach. That “threesome” zinger? Spicy, but it screamed frustration, not finesse.

Dating coach Connell Barrett, in a 2023 Men’s Health article, says, “Transparency in dating avoids traps—set expectations early to dodge scams.” A 2022 Pew Research survey notes 30% of daters report manipulative tactics, like leveraging sob stories for gain. Lily’s friend acting like a co-star, not a chaperone, smells like a hustle.

Jake’s right to reject the setup, but a quieter exit might’ve saved face. Barrett suggests clarifying costs upfront—like, “I’m covering us two, cool?”—to avoid public spats. Lily’s silence during the friend’s aggression hints at complicity or conflict avoidance. Readers, ever been blindsided on a date? How’d you keep your cool?

Here’s what Redditors had to say:

Reddit’s posse pounced on Jake’s saga like it’s a juicy group chat, slinging cheers, shade, and scam alerts. It’s like a barstool rant where everyone’s got a story or a sting to share. Here’s the crowd’s unfiltered vibe, packed with fire and snark:

Accomplished-Drop423 − NTA. You didn't invite the friend on the date, your date did. Even if this was genuinely for anxiety purposes, I think you dodged a bullet.

Own_Strength_7645 − as a woman, if I want someone there to ‘watch out’ they’re hanging out at the bar and acting nonchalant. not IN THE DATE???

judgingA-holes − NTA - They were just trying to get free food out of you. If this was really something that had to do with anxiety and she wanted her friend there then she should have paid for her friends or her friend to pay on her own, but to try to get you to pay for the both of them is just very entitled.

manda14- − NTA - this is a really weird expectation.

BeardManMichael − NTA. They ambushed you with a complete change of plans. Honestly from reading this it sounds like they both expected to use you and take advantage of you.. I'm glad you held firm and didn't tolerate any of their BS.

graveytrane − You shoulda brought a friend too and asked her to pay for everyone! Seriously though, I understand the protection aspect. But she could sit by herself at another table. Or at a close coffee shop and pay for herself or get her friend to pay for her.. It sounds like they were trying to milk you.

deathtoallants − I wonder if they do this gig often to score free dinners at nice restaurants on the regular. A practiced sob story about anxiety and a sympathetic past. Then to bully the mark of the night to pay for everything. What a weird story.

ImWithNeo − NTA at all. If she needed support why not make it a double date instead of having the friend awkwardly third-wheeling it?? As a female, I agree with you that this could’ve been them angling for a free dinner. I have heard of girls doing that.

Hirider34_2023 − This happened to me once. I agreed to meet a woman for drinks but when I get there she has six of her friends with her 4 of them where wearing wedding rings and where hanging all over men that where clearly not their husbands. Red flag #1. Then I was informed by my date I would be paying for all their drinks. Red flag number #2. I had already bought myself a beer so I finished it. Then got up left and never looked back. Blocked her as well.

asfarley-- − Ultra-based. Threesome or both of you ladies leave right now. Definite NTA.

These Redditors are hyped, crowning Jake a boundary boss or sniffing out a dinner dodge. Some cry “setup”; others wish he’d ghosted smoother. But do their takes nail the whole mess, or just chase the drama? One thing’s clear—Jake’s date crash has everyone buzzing. What’s your spin on his roast?

Jake’s tale is a tangy clash of trust, traps, and a date gone rogue. Calling out Lily and her friend wasn’t just about the bill—it was a stand against being played in a restaurant ruse. His public jab landed hard, but the real sting’s the what-if of Lily’s intent. Can modern dating dodge these ambushes? If a date pulled this switch, how’d you roll? Drop your thoughts below—let’s unpack this spicy flop!

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