29-year-old woman asks man to cover her $900 rent on their third date: 'I barely know her last name'

Author image for JR Atkinson
JR Atkinson • Writer and Editor
Mar 21, 2026 10:00 PM EDT

The question of who pays for what on a first date can be tough, but surely rent isn't one of those things. 

There might be stuff that comes up in the course of a relationship with someone that makes you rethink everything. Maybe you've been trotting along with someone, and everything is going fine, until one day it isn't. You learn something about them that changes the whole nature of your relationship. Maybe it's a revelation, or maybe it's just a detail that you weren't expecting. It's moments like these that determine whether or not you're built to last. Maybe it brings you closer together, or maybe it pushes you farther apart. Either way, you're probably going to need a little assurance along the way. Dating is tough, and it's not easy to open yourself up to new people. The man in this story learned that the hard way.

When you're in the early stages of dating someone, you probably want to put your best foot forward. You're not exactly hiding your flaws, but you're trying to lead with your good qualities. Ultimately, you want someone who will accept you at your low moments as well as your high, but you probably don't want to lead with struggle. That will always come up down the line. But dating is a vulnerable experience. You don't always know what's going to come up and what someone might ask of you. In this story, nothing could have prepared him for this question. 

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  • A man and a woman sit at a dinner table together on a date
    via Unsplash+ (Kateryna Hliznitsova)

    Image is representative only and does not depict the actual subjects of the story.

  • Relationships can sometimes mean sharing expenses, but it's important not to let this get out of hand. Maybe you pick up dinner every now and again, but a transactional relationship is something entirely different. That's what this woman was proposing, and way too early to boot. There are certain things that you should never ask someone you are casually dating, and this is one of them. But dating is all about taking risks, and this man learned that the wrong risk was just about to cross his desk. Keep reading to see what you think about this story and see what commenters had to say.

  • Girl (29, f) I am seeing asked me (32, m) to pay her rent on our third date. Is this a major red flag?

    I have been talking to this girl for about three weeks now. We met on Hinge and our first two dates were actually great. We had a lot in common and the chemistry felt real. She is 29 and works in freelance design so i knew her income might be a bit inconsistent but she always seemed to have her life together. Tonight was our third date and we went out for some drinks and appetizers at a nice spot downtown.
    via Glitchveil_2
  • Halfway through the night the vibe completely shifted. She got really quiet and then told me she was having some "temporary financial struggles" because a big client flaked on her. I felt bad and tried to be supportive but then she straight up asked if I could cover her rent for this month which is about £900. She
    via Glitchveil_2
  • said that since I work in engineering and "look successful" it probably wouldnt be a big deal for me and she promised to pay me back once her next project clears. I was honestly stunned into silence for a second. I barely know her last name and we havent even had the "exclusive" talk yet. I told her that I wasnt
    via Glitchveil_2
  • comfortable lending that much money to someone I just met and she got really defensive. She started saying that if I really liked her I would want to help her out of a tough spot instead of being "transactional" about it. She even brought up that her ex used to help her all the time without complaining.
    via Glitchveil_2
  • The rest of the date was super awkward and I ended up paying for the drinks and leaving early. Am I being too harsh or is it completely insane to ask a guy for rent money on the third date? I really liked her before this happened but now I feel like I was being scouted for my bank account rather than my personality. Has anyone else dealt with this kind of "investment" approach so early on?
    via Glitchveil_2
  • Two people hold mugs together on a date
    via Jonathan J. Castellon

    Image is representative only and does not depict the actual subjects of the story.

  • Commenters gave some hard truths.

    Tall-Play-7649 dude it's a sham ffs, block her + move on, the chemistry wasnt "real"
    via Tall-Play-7649
  • RD_in_Berlin Oh my god yes, cut her off immediately. You shouldn't even have to ask.
    via RD_in_Berlin
  • Avtomati1k One red flag is asking for money, second is saying that u look like u wouldnt have a problem with it financially, third is how she behaved after u said no. So, a plethora of red flags?
    via Avtomati1k
  • IndicationKey3778 Lmao no green flag. Pay my rent too
    via IndicationKey3778
  • LegitimateKnee5537 Paying rent is territory that only comes with getting her pregnant.
    via LegitimateKnee5537
  • CappriGirl That's mad. Run, my friend.
    via CappriGirl
  • JaeCrowe I dont need to read a single word past the title to know the answer to this one
    via JaeCrowe
  • MatchboxVader22 No you should not pay for her rent. Cmon man. I'd be moving on from her immediately
    via MatchboxVader22

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relationship advice dating fails relationship relationship status dating nightmares story money healthy relationship dating
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