Anonymous
Post 01/29/2026 18:36     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:I met a guy on Instagram and we went on two dates. On the second date he asked about my work. I said I’m taking a break for now, which is true. Later it came out that I’m financially independent due to family money / a trust fund.
His tone immediately changed. He made snide comments like “must be nice not to have to work” and implied I must have an easy or unmotivated life. It didn’t feel playful — it felt judgmental.
After the date he continued calling and texting me, but I felt uncomfortable enough that I ended up ghosting and blocking him.
I’m not flashy, I live a normal life, and I’m not opposed to working in the future. I just didn’t expect this reaction from this guy who is quite successful himself.
So I’m genuinely curious — is being a “trust fund baby” a turn-off when dating? Or did I just meet the wrong guy? What do men really think of women like me?


You might believe you're living a normal life, but that's not the case.
What a billionaire would consider normal is completely different from what a millionaire or someone from a lower class would think.
You're stuck in your own bubble and disconnected from reality.
A normal life doesn't mean you can just take a break from work whenever you feel like it.

Anonymous
Post 01/29/2026 18:36     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:Well, what do you do all day?

I graduated from an Ivy League school and am just taking a well-needed break. Hobbies including traveling, golf, Pilates, etc.
Anonymous
Post 01/29/2026 18:30     Subject: Date made snide comments about me being a trust fund baby
He sounds jealous op. Drop him like a hot potato.
Anonymous
Post 01/29/2026 18:29     Subject: Re:Date made snide comments about me being a trust fund baby
With any luck, OP will find a more circumspect golddigger to date
Anonymous
Post 01/29/2026 18:28     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:Most people who are in this situation are savvy enough to have a prepared response that is truthful but not the whole truth in order to avoid the target on your back until the person is trusted.

I’m surprised given your assets that your parents or guardians haven’t taught you this by now.

Lesson learned.


All of this.
Anonymous
Post 01/29/2026 18:28     Subject: Date made snide comments about me being a trust fund baby
Not compatible. You don't want someone who doesn't appreciate you for being an insecure trust fund baby.

Anonymous
Post 01/29/2026 18:28     Subject: Date made snide comments about me being a trust fund baby
You met a guy with issues about people or maybe just women with a moneyed background.
It was never going to be a match.
Plus he was rude.
Anonymous
Post 01/29/2026 18:26     Subject: Date made snide comments about me being a trust fund baby
Most people who are in this situation are savvy enough to have a prepared response that is truthful but not the whole truth in order to avoid the target on your back until the person is trusted.

I’m surprised given your assets that your parents or guardians haven’t taught you this by now.

Lesson learned.
Anonymous
Post 01/29/2026 18:26     Subject: Re:Date made snide comments about me being a trust fund baby
I thought my (now) husband was a drug dealer because he didn't fess up about the trust fund....32 years later it all worked out - but it was pretty unrelatable at the time. We still laugh about it now.
Anonymous
Post 01/29/2026 18:25     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:I think you could have just said “I’m living off savings,” and left it at that. The way you phrased it turned me off too.


You're not going to be able to leave it at that.
Anonymous
Post 01/29/2026 18:24     Subject: Date made snide comments about me being a trust fund baby
“I’m not flashy, I live a normal life, and I’m not opposed to working in the future.”

You seem a little clueless if you have to ask this question to begin with. But in a world where most people need to work to support themselves, are you really not able to see how your statement above might come across? Many would instantly conclude you have little in common with their lives
Anonymous
Post 01/29/2026 18:23     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:
Anonymous wrote:I met a guy on Instagram and we went on two dates. On the second date he asked about my work. I said I’m taking a break for now, which is true. Later it came out that I’m financially independent due to family money / a trust fund.
His tone immediately changed. He made snide comments like “must be nice not to have to work” and implied I must have an easy or unmotivated life. It didn’t feel playful — it felt judgmental.
After the date he continued calling and texting me, but I felt uncomfortable enough that I ended up ghosting and blocking him.
I’m not flashy, I live a normal life, and I’m not opposed to working in the future. I just didn’t expect this reaction from this guy who is quite successful himself.
So I’m genuinely curious — is being a “trust fund baby” a turn-off when dating? Or did I just meet the wrong guy? What do men really think of women like me?


Yes, it will definitely turn me off. I can do it tomorrow adds nothing to you as a person.


+1. OP is probably a troll. Surely most people would understand this is a negative trait.
Anonymous
Post 01/29/2026 18:22     Subject: Date made snide comments about me being a trust fund baby
OP, this is not something to share on a second date. This info can attract freeloaders.

I'd simply say you are currently between jobs and living on investments and leave it at that.

I would not share that you have a trust fund with someone until you are talking marriage with someone.

Anonymous
Post 01/29/2026 18:22     Subject: Date made snide comments about me being a trust fund baby
I think you could have just said “I’m living off savings,” and left it at that. The way you phrased it turned me off too.
Anonymous
Post 01/29/2026 18:21     Subject: Date made snide comments about me being a trust fund baby
Anonymous wrote:You should ask around in your network to find someone similar to date. I’m dead serious. There’s a reason why all the wedding announcements in the NYT were between people from rich families. Someone who had a similar upbringing to you wouldn’t do a double take when you mentioned you had a trust fund and then you could know that you were on the same page re: money.


I usually date guys from similar backgrounds, just tried something different this time. I’m turning 24 soon, and just looking for a long term partner.