How to Navigate Dating When Rich Or Wealthy?

[Solomon]

Disclaimer: I'm curious to hear from successful members about this. No shade to members that don't fit the bill but this is for people who actually experience this and not 2nd or 3rd hand accounts(keyboard jockeying)

I don't consider myself wealthy not even close. However, I'm doing far better now than when I started on this site as a broke 24-year-old arrogant kid working 2 jobs. I've noticed that in the last 4 years the more my income improves the more it brought me into spaces and circles I haven't had access to before(Thousandaires and multi-millionaires, including D-List celebs). In the last few years, I have dated women and/or gone on dates with women who wouldn't have given me the time of day before, with financial success discerning genuine interest can be challenging at times.

I would love to hear personal stories and Red flags to look for

I find Social Circle to be the best however it's not always the best. I.e. I dated a hot chick in 2023 my millionaire buddy introduced me too but she was bat**** crazy and my buddy didn't give me the heads up that she was psycho. Needless to say I stopped hanging out with said circle as much. Below are some actions that I'm already taken

• Some Gold diggers are easy to spot, they tend to be so obvious and obnoxious that I avoid them no matter how hot they are
• I don't do fancy dinner dates or take girls to fancy restaurants unless we are exclusive
• I sometimes don't even bring women around my place as I value my privacy and yes I have rented hotel rooms as advised by my attorney at times
• I find women who tend to do well salary-wise are much more relatable although I prefer submissive women, I find women who don't make money tend to fit the bill better
• If I meet a woman in the field or online I present myself below my means although In social circles it's hard to keep it a secret

Some questions I have

• Red Flags: What are the signs or behaviors that make you cautious about someone’s intentions?
• Dating Strategies: How do you approach dating to ensure the person is interested in you for who you are, rather than your bank account? especially if they know you're doing well?
• Balancing Transparency and Privacy: How do you handle conversations about your financial status early in a relationship? Do you keep it under wraps initially, or do you prefer to be upfront?
• Advice for Others: What advice would you give to other successful men facing similar situations? Are there any specific strategies or mindsets that have worked for you?

Thank you

 

[DreamAgain]

This is difficult to answer, perhaps it is impossible actually. You can really only be sure when you find one who was with you while you were struggling or rising up to where you are now.

 

[pipeman84]

How do you approach dating to ensure the person is interested in you for who you are, rather than your bank account? especially if they know you're doing well?

If she's not a virgin then 99.5% it's not YOU, it's your bank account. If she's +25yrs old and not a virgin then make that 99.99%.
But if you want to go for that 0.5 - 0.1% exception, then spend 60 days with her using as little money as possible ... imagine you're in high school ... fancy dinners, expensive gifts, travels are out of the question. Just quality time together that cost nothing or next to nothing ... walks in the park, at the mall and so on. It should become obvious very soon if she enjoys being with you or not.

 

[RickTheToad]

Some say fake it until you make it. In the metro NYC area, we have a lot of fakers living off credit to portray a life that isn't real. However, you can join them if you wish. Join the exclusive clubs; there's several in NYC, Greenwich, Stamford and Westport. In your area, just go to the wealthy areas and smooze. It's best to become a member; if possible.

The game only last so long. Eventually, you will be made.

After my divorce a decade ago, I went to different places and stayed in AirBNB's under an assumed name. I only used cash or I picked up one of those pre-paid cards where you can go online to customize with an assumed name. Never carried ID or any personal information. I placed about $1500.00 on the pre-paid visa which had the assumed name, not my real name and I hopped from place to place in different nice AirBNB's. I am not sure if this is possible anymore with the stricter AirBNB's, but you may be able to book under an LLC with AirBNB and still do the rest of the items I did.

It's hard to be someone else nowadays with all the technology. With a burner phone, pre-paid credit card and no personal on your person, it is possible. Remember, if your real name is Jim Smith in Stamford, CT, I can find out a lot about your personal life with Spokeo and a few other sites. Now, if you an assumed name, from another city/state, it would be much harder. The facial recognition software is mainly in larger venues and gov't facilities. If you are doing nothing illegal, then there's really nothing to worry about. You can, however, pickup some creams and glasses which will also deflect the facial AI algorithms. Again, it just depends on what you need all of this for, and how deep you want to go to be someone else.

 

[Chow Mein]

When you accumulate financial wealth, that becomes your priority. You protect and grow it at all cost.

Be weary of the women (people) you let into your life. I don’t mind spending money on experiences with the plates that have already proved themselves.

I don’t talk about specific financials while on a first date. Women will internally assess how much you’re worth by the experiences you share with them. Women get the hint I’m financial stable, but that will never be a topic of conversation. those that don’t get it and continue to ‘investigate’ can take their leave.

 

[Clockwerk50]

I’m broke as hell so for that reason…

 

[BeExcellent]

Poor mouth. While I disagree about actively trying to hide who you are (if I'm going to a Charlie Trotter's type place.....I'd be going there anyway.....don't go to Red Lobster just to pretend you aren't a Charlie Trotter's guy for example).....I also think it is worthwhile to help someone understand the obligations and responsibilities of having something includes.

Last week I dropped 3K on repairs to a rental unit and 5K on oral surgery for my daughter. Many people don't make that in 2 months. I talk about having to put those things on cards (and downplay that I pay them off quickly.)

I do not share financial details with anyone who is not of similar level of wealth than I, and I'm somewhat opaque even then. People can see that I drive a very expensive car (bought used), wear expensive clothes & jewelry, bought mostly used, and I pay attention to someone's ease being around affluent people. I don't gush about someone's plane, or yacht, or racehorse or expensive home. I get uncomfortable when someone is unaccustomed to the trappings of wealth, because that demonstrates a lack of discretion and a sense of "OMG he has XYZ......"

So you'll have to cypher who doesn't have the elegance to navigate that world (or lacks the discretion to ask privately about things she doesn't know)......

You also would do well to avoid women who feel entitled to what you have worked so hard for (if they never make an effort to pick up the check or if they expect shopping trips or you to cover her rent/gas/bills etc.)

And you'd also do best to avoid women who think they deserve your resources in exchange for her looks. That is more subjective. So use your judgement.

The way to figure out these things is to listen, pay attention and downplay your wealth while still living your life as you were already doing. Poor mouth around those whose motivations you do not know.

I out earn my man by a multiple. He had very little idea and I still do not discuss specifics with him. Our finances are individual, not joint because we had lives prior to one another.

Trusts are your friend. Protect your wealth in advance from others who would take advantage.

 

[RickTheToad]

Poor mouth. While I disagree about actively trying to hide who you are (if I'm going to a Charlie Trotter's type place.....I'd be going there anyway.....don't go to Red Lobster just to pretend you aren't a Charlie Trotter's guy for example).....I also think it is worthwhile to help someone understand the obligations and responsibilities of having something includes.

Last week I dropped 3K on repairs to a rental unit and 5K on oral surgery for my daughter. Many people don't make that in 2 months. I talk about having to put those things on cards (and downplay that I pay them off quickly.)

I do not share financial details with anyone who is not of similar level of wealth than I, and I'm somewhat opaque even then. People can see that I drive a very expensive car (bought used), wear expensive clothes & jewelry, bought mostly used, and I pay attention to someone's ease being around affluent people. I don't gush about someone's plane, or yacht, or racehorse or expensive home. I get uncomfortable when someone is unaccustomed to the trappings of wealth, because that demonstrates a lack of discretion and a sense of "OMG he has XYZ......"

So you'll have to cypher who doesn't have the elegance to navigate that world (or lacks the discretion to ask privately about things she doesn't know)......

You also would do well to avoid women who feel entitled to what you have worked so hard for (if they never make an effort to pick up the check or if they expect shopping trips or you to cover her rent/gas/bills etc.)

And you'd also do best to avoid women who think they deserve your resources in exchange for her looks. That is more subjective. So use your judgement.

The way to figure out these things is to listen, pay attention and downplay your wealth while still living your life as you were already doing. Poor mouth around those whose motivations you do not know.

I out earn my man by a multiple. He had very little idea and I still do not discuss specifics with him. Our finances are individual, not joint because we had lives prior to one another.

Trusts are your friend. Protect your wealth in advance from others who would take advantage.

I hear you. I just dropped 30k on new siding for a rental. AMEX gave me an offer of a 125k in points for 10k spend. I put 10k on that card, and the remaining 20k on my AMEX business blue. I earned 165k in free points and I took a short vacation to unwind on point to Europe. I'm a nut on paying balances off, so I pulled from my rental reserves to pay off the 30k in siding.

The dental, you may be able to get reimbursed from your LLC if you are an employee and you setup a IRS approved cafeteria plan / Section 125 or MERP. The dental work would now be a business deduction since it's an employee expense. Of course, check with your CPA on this, as I am not an accountant, but it's something many business owners legally do.

 

[Plinco]

One thing you could do is dress like everyone else and drive a Honda. That eliminates the gold diggers right there.

That said, if looking rich is your thing, then I'd say just get to know the person and asses their character through experience.

 

[Hamurabimbi]

Go for younger women.
Most aren’t all that impressed with wealth.

 

[FlirtLife]

Years ago I went on a lot of first dates from Tinder. I would reveal that I am "unemployed" but have "saved up some money". The word "some" is a severe understatement, but it seems to be enough of an answer on a first date. It might be more accurate to say I retired early, so "unemployed" is also shading the truth a bit. Not technically false, but definitely hiding information. A first date may be the last date, so I'd rather only reveal limited information to a stranger.

Bill Maher is rich enough to fly private, and said gold diggers will ask him about his nice watch. If you find women commenting on luxury items and how much they're worth, that could be a red flag signaling a gold digger.

I don't wear a watch or jewelry, nor any brands or luxury clothes. There's no hints about my investment accounts from looking at me, so I've never needed to downplay it (but I have "I don't own a car" ready, just in case). I'm afraid I haven't had to contend with gold diggers, because I provide no indications they should pursue me.

 

[AmsterdamAssassin]

Years ago I went on a lot of first dates from Tinder. I would reveal that I am "unemployed" but have "saved up some money". The word "some" is a severe understatement, but it seems to be enough of an answer on a first date. It might be more accurate to say I retired early, so "unemployed" is also shading the truth a bit. Not technically false, but definitely hiding information. A first date may be the last date, so I'd rather only reveal limited information to a stranger.

I retired at 44. I don't tell anyone about my finances. I live a fairly humble existence well within my means, because I don't put much stock in material wealth, but my time is valuable. Cars are a useless but expensive nuisance in Amsterdam Centrum, so I don't own a car, but I use share-cars / rentals if I need one. For my daily needs, I have a motorcycle, bicycles, or use public transport.

And my activities don't attract gold diggers, who like to leisurely enjoy the lap of luxury. Through my previous work and contacts, I've been around enough rich people to understand part of the attraction, but if you don't want to be rich and/or famous, most of these people tend to be boring company. I prefer hanging out with creative / artistic people and preferably not the 'celebrities'.

If I would get obscenely rich, I would probably hide my wealth and stay out to the limelight as much as possible.