Thursday, March 23, 2023
HomeRelationship AdviceTLDR: Woman gets pissed because I've dated other women older than myself.

TLDR: Woman gets pissed because I’ve dated other women older than myself.

Hi all. Just want to run a situation by you. I (30M) have been talking to this woman (26F) for a couple weeks now. We’ve met twice and hit it off in person but some wild shit happened today that I need help evaluating objectively.

Basically we were texting back and forth today and the subject of my past dating life came up. She asked how old the women I’ve dated are.

Now I admit this is the first time I get involved with someone younger than myself. I’m pretty attracted to women older than me, and have had relationships with women between 3-5 years my senior. Not that big a gap but I just have a thing for them.

So today we’re talking about money. I let her know in the grad school program I just finished, a lot of students came from money and would always be inviting me to outings that I just could not comfortably fit into my budget because my daddy isn’t an oil baron.

She tells me basically that she now understands why I go for older women, because usually they’re more financially stable and established. I let her know that when I was working before my program I was just as financially conscious and established as whoever I was in a relationship with and was more than happy to go 50/50 on expenses.

At that point she called me a cheapskate who has bad manners because no woman should ever have to pay for a meal, and she would never have intimate relationships with a guy who didn’t pay for her food because that’s just being a gentleman.

She let me know she had me all figured out and that no wonder I only dated only older women who were ‘dumb with no self respect and would give it up for some cheap guy who makes them pay for stuff.’

I tried to just play it off and told her that her evaluation of me wasn’t really based off reality and she really didn’t have a reason to make all those assumptions but she kept railing on about it. Basically telling me it makes so much sense I go for women who make more money than me (we’ve never even touched the subject of income and I wasn’t about to drop my current salary on her) and are stupid and have no self respect (not sure how she’s achieved omniscience on my past relationships).

So I guess my question is am I insane or is this a massive red flag?

View Reddit by plentifulguiltView Source



  1. Red flag? It’s a deal breaker. You shouldn’t continue communication with her, and you definitely shouldn’t see her again. I dated a guy once who always liked to tell me who I was. He couldn’t be further from the truth, and ..*surprise* ..he ended up being manipulative, and emotionally abusive.

  2. Leave her. She’s insecure. She heard you usually date older women and her being a younger one made all her insecurity flare up. From that brief snippet of things she’s said she sounds like a good bullet to dodge.

  3. This is exactly why you date older women. Twenty-somethings (especially those under 27) can be very insecure. I think you appreciate the confidence slightly older women have.

  4. So she basically tells you that she’s a princess and if you don’t pay for every scrap of food that enters her lameo mouth that she is going to think you’re less then a man. Sheesh talk about entitlement, hopefully this is an ex because she just told you everything you need to know

  5. >At that point she called me a cheapskate who has bad manners because no woman should ever have to pay for a meal, and she would never have intimate relationships with a guy who didn’t pay for her food because that’s just being a gentleman.

    Do you really want to date someone that thinks like this ?

  6. Someone who makes such sweeping assumptions about you now, and tells you that you’ll pay her way, all the way if you’re ever together – why bother wasting even another minute talking to her?

  7. Welcome to /r/relationship_advice. Please make sure you read our [rules here.]( We’d like to take this time to remind users that:

    * We do not allow any type of [am I the asshole? or situations/content involving minors](

    * Any sort of namecalling, insults,etc will result in the comment being removed and the user being banned.

    * No referencing hateful subreddits and/or their rhetoric. (Includes, but is not limited to: red/blue/black/purplepill, FDS, MGTOW, etc.) Any infractions of this rule will result in a ban. **This is not an all-inclusive list.**

    * All bans in this subreddit are permanent. You don’t get a free pass.

    * What we cannot give advice on: rants, unsolicited advice, medical conditions/advice, mental illness, letters to an ex, “body counts” or number of sexual partners, legal problems, financial problems, or situations involving minors and/or abuse (violence, sexual, emotional etc). All of these will be removed and locked. **This is not an all-inclusive list.**

    If you have any questions, please send us a modmail.


    #This is an automatic comment that appears on all posts. This comment does not necessarily mean your post violates any rules.

    *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/relationship_advice) if you have any questions or concerns.*

  8. Yikes, huge red flag. There is nothing wrong with being in a relationship where one person contributes more money than the other, and there is nothing wrong with both people in the relationship contributing equally. There is a huge problem when someone says you’ve been doing it all wrong and degrades you for your choices in previous relationships. It doesn’t sound like she’s very nice to you.

  9. She’s not your GF… maybe consider keeping it that way.

    It seems like *she* expects you to give her everything she wants (financially) and your texting is the interview to see if you would be her next sugar daddy.

  10. The red flag is so big that I think I could use it as a cape…holy shit. On a sidenote, as an older woman I would really like to know what makes us so bad. She’s going to become one of us in the future anyway.

  11. No you’re not insane and yes it’s a red flag and hopefully you ended communication with her because you don’t need someone like that in your life.
    For what it’s worth I’m 33f and I refuse to let a guy pay for everything. If he wants to pay sometimes, fine, but I also enjoy taking him out on dates and making him feel special. Find a woman that makes you feel special. She’s trash.

  12. sounds like she spends a lot of time on the internet, maybe tiktok. I’ve never considered asking men how old the women they date are. I assume they’re usually within 5 years of their own age, that’s the most common. People who have it together ARE attractive. Sounds really disgusting and agist on her part. Again, probably based on some weird toxic ideas on social media ie. women over 30 are worthless, so they have no respect and pay for food lol. OK…. ditch her and find a lady.

  13. She’s looking for a meal ticket and you’re not giving the right feedback to her “gentlemanly” one sided requirement in a relationship. She’s the kind of people that will forever looking to “upgrade” for her relationships. I would just keep it a casual thing with her and invest yourself in a better person.

  14. Massive red flag! I’m a woman dating someone a good bit wealthier than me who typically pays for me when we go out. That is an arrangement we are both comfortable with. That’s what matters. Do not let someone shame you for that, especially when it’s rooted in sexism.

    She was probably raised in a household with strict gender roles. My honest advice is to stay away from people who believe things like that, they are typically incredibly toxic. Don’t see her again.

Comments are closed.

Most Popular