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

by Ankit
September 26, 2025
in Relationships
Reading Time: 5 mins read
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He met her through Bumble, their connection sparking quickly as they shared stories and vulnerabilities. She revealed her struggles with anxiety and past heartbreaks, painting a picture of someone cautious yet hopeful, eager to find trust amidst the scars left by cruel exes.

When she asked to bring a friend to their dinner date for comfort, he hesitated but agreed, wanting her to feel safe. Yet, as they arrived and he saw the friend equally dressed up and lively, a ripple of uncertainty crept in—this night was unfolding into something far more complex than he had anticipated.

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 B*mble a...

We really seemed to hit it off, but she confided...

We get around to scheduling a dinner date at a...

I was a little surprised at first, and thought it...

I'd heard about this kind of thing before anyways so...

The problem arises once we actually get to the date,...

if she planned to just hang out, if she was...

telling me that she's basically a part of the date...

but her friends bill wasn't ever mentioned) Now in my...

but I didn't figure this would mean they'd actually be...

and told the friend, "I'd even be cool if you...

Obviously they left and the date didn't end up happening....

and rejecting the date altogether,, but I can't help but...

or gone along with it and just break it off...

What do you think of this story?





THIS STORY SHOOK THE INTERNET – AND REDDITORS DIDN’T HOLD BACK.

Own_Strength_7645 as a woman,

if I want someone there to 'watch out' they're hanging...

judgingA-holes NTA - They were just trying to get free...

If this was really something that had to do with...

pay on her own, but to try to get you...

manda14- NTA - this is a really weird expectation.

BeardManMichael NTA They ambushed you with a complete change of...

Honestly from reading this it sounds like they both expected...

I'm glad you held firm and didn't tolerate any of...

graveytrane You shoulda brought a friend too and asked her...

Seriously though, I understand the protection aspect. But she could...

Or at a close coffee shop and pay for herself...

ImWithNeo NTA at all If she needed support why not...

third-wheeling it?? As a female, I agree with you that...

deathtoallants I wonder if they do this gig often to...

A practiced sob story about anxiety and a sympathetic past....

Silver_Advantage_536 NTA, this was just weird asf.

asfarley- They really expected you to pay for her friend...

Threesome or both of you ladies leave right now. Definite...

IceCorrect NTA Congrats you are another bad experience from her...

After reading through the Reddit comments, it’s clear that many people empathize with the original poster’s (OP’s) mixed feelings about the dinner date setup. While some praised OP for being understanding and accommodating of the girl’s anxiety, others pointed out that bringing a friend along on a first date can complicate things and raise questions about intentions on both sides. The consensus seems to be that while supporting someone’s need for comfort is important, clear communication about boundaries and expectations is crucial to avoid misunderstandings.

Personally, it seems like OP handled the situation with kindness and openness, even if it didn’t unfold exactly as a typical first date might. Navigating dating when mental health and past trauma come into play requires patience and flexibility. Ultimately, every dating experience is a learning opportunity, and respecting each other’s needs—even when they challenge traditional norms—can lead to more genuine connections or at least valuable clarity moving forward.

Ankit

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