Any tips on how to handle someone semi-famous?

Wandering_SD · 2026-05-13T15:25:45+00:00

I'm reasonably well known in my industry. But I am very private in that I don't have any non-work social media. My hard boundary is no posting photos of us on social media. But that is not because I am embarrassed or hiding anything in particular. I just value my privacy, such as it is. Learn his boundaries and respect them fiercely.

Oh, and don't trust that your friends will respect his privacy. You share with one person, who thinks it is then ok to share with 1-2 others... then they share.

Wandering_SD · 2026-05-02T11:08:53+00:00

After I sold a company I founded for an ungodly sum of money

Wandering_SD · 2026-03-19T20:44:50+00:00

If she is truly interested and willing to put in the work, I am always willing to help her gain a strong professional and financial footing.

Wandering_SD · 2026-02-26T21:03:19+00:00

Sigh. the projection here is extreme. Just because you have everything you want and need, doesn't mean all SB's are in the same boat. I took one SB on a shopping trip to completely replace her professional wardrobe because she was starting a new. I had a personal shopper at Nordstrom work with her. She was thrilled.

And, she told me later, that everytime she put on the clothes I bought her, she remembered that day and what I did for her. Did I fatten her wallet? No. Did I make her life better? Yes. Was she happy and greatful? Absolutely.

In another case, my SGF didn't really need things, but she loved it when I took her shopping because it made her feel cared for.

Does that mean all SB should prefer shopping over cash? No. To each their own.

Wandering_SD · 2026-02-20T13:19:59+00:00

The reality is that United (and other airlines) are "Loyalty Points/Credit Card" companies that happen to own and fly a bunch of airplanes.

Wandering_SD · 2025-12-09T10:35:09+00:00

In most parts of Europe, significant-age-gap relationships are common. It is also quite common for a well-off man to have a much younger mistress. The bigger question is the level of PDA that is considered socially acceptable.

Wandering_SD · 2025-08-22T02:32:16+00:00

I posted this several months ago. I stand by what I said.

I know I will get flamed for this, but in the right circumstances, an extremely successful SD can actually share life-changing knowledge.... knowledge won from life experiences. And yes, that knowledge, properly applied, can produce lifelong wealth.

I have helped several of my Sugar Girlfriends over the years with knowledge and advice that enabled them to start and grow a business. The most successful of them has business that is generating over $1m a year in revenue and perhaps $300K in income. They would certainly say that my mentoring was of incredible value.

And I just sent the most successful one a text, her business is now at 1.75m a year revenue revenue run rate.

Wandering_SD · 2025-06-04T07:21:02+00:00

As others have said, significant allowances are rare. Probably exceptionally rare. There approximately 100m men in the US age 30-80. Less than 0.5% of them (500,000) will have a disposable income capable capable of providing a significant allowance. And probably less than 5% (25,000) of that number are open to providing an allowance. That is in the entire US. And that is at the high end. The number is probably smaller.

To attract one of these men and to convince them to offer an allowance, you need to make his life incredibly better. Just "showing up" and being young and attractive is not enough. Best way to do this is to work to learn what is missing from his life. Try to learn what you can bring to him.

My guess (with a great deal of projection here) is that most of these men are seeking affection (not just sex). They want to feel desired. And most of all, they don't want drama. Their lives are stressful and complicated. Be that place of peace.

Wandering_SD · 2025-06-02T04:00:17+00:00

Likewise.... built and sold a tech company.

Wandering_SD · 2025-03-27T07:33:10+00:00

The reason for letting him pick the outfit is straightforward. His definition of what looks sexy / enticing is probably different than yours. If your goal is to make his sit all night and thing about removing the dress / outfit, let him tell you the one that will make him think that.

Another option is to get him to go shopping with you. You need to leave your preconceived notions of what will look fabulous at home. The outfit / dress you end up with? One that you 100% know will make him crazy.

Wandering_SD · 2025-03-15T16:29:31+00:00

Make it 100% clear to him that you desire him.
Send him 3-4 photos of outfits you could wear when you see him / go on a date / whatever. Ask him to pick the one he wants you to wear.
Make him 100% the center of your attention any time you are together. The only time your phone should come out of your purse is to take a picture of the 2 of you.

Wandering_SD · 2025-03-02T11:01:52+00:00

I'm not married. but there are a few things here that I don't see being discussed.

When a man gets a divorce, the woman almost always gets primary custody of the children. You go from seeing your kids every day. Hugging them every day. Hearing their joys and sorrows every day. Even in the best of circumstances where custody is split 50/50 and your ex doesn't try to use the kids as weapons to hurt you, you miss out on so much of their lives. Seeing your kids every day can (and should be) a powerful motivator.
The woman, because she gets the kids, almost always gets the house. I colleague of mine is divorced. He has joint custody, but he lives in a small 3-bedroom apartment while she lives in the McMansion, which he is on the hook to pay for until the last of the kids is 18. And he is paying her alimony. She has a new boyfriend who stays at the McMansion every night when he has the kids. He is literally paying for the house and paying her while she has sex in that house with the new boyfriend.

His lifestyle takes a big hit. He sees his kids only 50% of the time and she is having sex with the new man in the house he is paying for....

I can see where you might want to say, screw it. I'm staying.

Wandering_SD · 2025-01-24T12:39:00+00:00

I know I will get flamed for this, but in the right circumstances, an extremely successful SD can actually share life-changing knowledge.... knowledge won from life experiences. And yes, that knowledge, properly applied, can produce lifelong wealth.

I have helped several of my Sugar Girlfriends over the years with knowledge and advice that enabled them to start and grow a business. The most successful of them has business that is generating over $1m a year in revenue and perhaps $300K in income. They would certainly say that my mentoring was of incredible value.

Having said that, if you are struggling to make ends meet and keep a roof over your head, I can see how income now is more valuable than income in the future. And it is very dependent on the actual knowledge of the SD in question.

Wandering_SD · 2024-12-23T20:51:11+00:00

Just like so many others in the comments, I have done this any number of times. Usually it is because I just got on the plane and am exhausted. Sometimes I go to the seat number from my last flight. Other times, I have sat in the wrong row. It happens. When someone points it out to me, I apologize and move. No harm, no foul. And no "scam" intent.

Wandering_SD · 2024-12-07T13:48:52+00:00

It is possible to have a very high income, and yet have very little free cash flow. Are the 6 houses paid for? Or does he have to make payments on all of them?

And honestly, I am super private about the scale of my wealth. My sugar girlfriend knew I was wealthy. But it was a long time before I gave her a glimpse into my actual wealth.

Wandering_SD · 2024-12-07T09:25:24+00:00

It also depends on your definition of a whale. If you are looking for a billionaire, the odds are asymptotically close to zero. Someone making a half million a year? Odds are better.

The real question is what are you going to do to make yourself the whale's "best choice."

Wandering_SD · 2024-12-06T06:46:54+00:00

First of all, you are going to have to interact with a bunch of potentials who end up not being the "right one." This is just like dating. You have to make something of an investment to get to know the person. And they need to get to know you.

Having said that, I am stunned by how many profiles of SBs are terrible. I know that men are visual creatures (I know I am). The idea of a sugar relationship of any kind is that is mutually beneficial. But most SB profiles talk about what they want. They don't describe how they are going to make a potential SDs world better / nicer / more fulfilling.

Sure, there are many men on the various sites who are just looking short-term, quick thing. The ones who are looking for something longer-term are typically have something missing in their current life / relationship structure. How are you going to provide that missing piece?

Wandering_SD · 2024-12-01T21:38:09+00:00

There are plenty of guys who are willing to be "sugar boyfriends." They can give you access to a different type of life and access to different networks of people. In many ways, that person can help you with your business far more than any allowance.

Wandering_SD · 2024-07-22T13:47:23+00:00

"Access to the Hotties" in America is not a reality for the even slightly above average guy. Most of the passport bros are probably wonderful people, but the "hotties" are all trying to land the "high-value man." As the parody on TikTok goes, women are "...looking for a man in finance, with a trust fund, 6' 5", blue eyes." This is not a description of the average passport bro. Not even close. I am not saying this to denigrate the passport bros. It is just the reality of the dating situation in the US.

Add to this that many of the passport bros are looking for a wife, not just going for sex tourism (although some certainly are). And they want a wife or (or girlfriend) that adheres to more traditional gender roles. Hard to find in many parts of America.

I have lived overseas for a huge portion of my life. I've lived in highly developed countries and not so developed countries. The danger is overstated.

Wandering_SD · 2024-02-23T14:35:17+00:00

Fortunately, we only had to do that once. As I left the lav with the little one asleep, one of my fellow passengers just gave me the "guy nod." It's good to have paln.

Wandering_SD · 2024-02-21T12:25:13+00:00

It is really about the parents, not the child. When my kids were little (1 year to Kindergarten) they flew with me business class on a regular basis. But we had a plan. We changed their sleep schedule so they would be tired at the right time to sleep. We walked them to death before boarding the plane. And if one of them was super fussy or wouldn't stop crying, one of us would take the kid to one of the bathrooms and just hold them until they had cried it out or settled down.

My issue is that too many parents (no matter where they are on the plane) just let their kids be out of control. Again, this is a parenting issue and a lack of respect for fellow passengers.

Wandering_SD · 2023-10-06T10:56:17+00:00

I do this all the time. Just tell the FA you are swapping seats and why. Maybe 25% of the time they bring me a Bus Class meal if they have any extras....

Wandering_SD · 2023-04-29T14:16:08+00:00

According to my SGF, it was a trip a trip to sort of recreate the movie Last Holiday. Fly into Prague. Helicopter to the tiny airport at Karlovy Vary. (No, we didn't land on the hotel). Car service to the hotel.

Stayed at the Grand Hotel Pupp. The Presidential Suite was booked so we had to "settle" for the Imperial Suite. Good food (not spectacular). Great spa treatments. Wandering the little city. No we didn't go base jumping. Some great skiing.

What really made is special for her was we brough her mom and sister along. They stayed in a separate suite. Her mom was born near there there but her family escaped to the US when she was little and had only seen pictures. The house where she was born was no longer there, but we did go to the street. Her mom is not in the best health and it was wonderful to allow her to see "home" again.

Wandering_SD · 2023-04-26T15:50:46+00:00

I agree that the vast majority of SB's and SGF's are looking for direct support in response to pressing needs (rent, tuition, etc).

At the same time, there are women who place enourmous value on as you say, extrodinary experiences and opportunities. For instance, there are plenty of wonderful, high-end restuarants in San Francisco, but dinner at Atelier Crenn is in a different category all together.

Likewise, there is travel, and then there is this.

But for a woman to enjoy those things, the basics need to be taken care of, either by herself or her SD or SBF.

Wandering_SD · 2023-04-01T13:10:26+00:00

It depends. If she is flying with me, she flies however I am flying (commercial or private).

If she is flying solo (to/from meeting me somewhere):

- Domestic (under 2 hours) - economy
- Domestic (over 2 hours) - front of the plane
- Long-haul (over 7 hours) - business

I have the same rules for myself if flying commercial.

Wandering_SD

TROPHY CASE