How can a young stud meet a rich old lady?

February 27, 2005 7:28 PM

How, and where, does a twenty-something guy find a rich sugar momma?

My friend is a good-looking young guy, and wants to meet an old lady that'll spend money on him, make him over, etc. He's willing to give up all of his personal opinions and control of his appearance. We were trying to think of places he could meet older women looking to spoil a cute young guy, but we were stumped. Any ideas?

posted by ThePinkSuperhero to Human Relations (39 answers total)

IANAG, so all I can suggest is joining a social club or group with demographics matching his 'interests'. In this case, he might seek out local bridge, knitting, or scrabble circles, and socializing there in hopes of getting snatched.
posted by onalark at 7:43 PM on February 27, 2005

Response by poster: fyi, according to onalark via AIM, IANAG is- I Am Not a Gigolo.
posted by ThePinkSuperhero at 7:44 PM on February 27, 2005 [2 favorites]

I'd say to target hotel bars, and conferences/conventions, and country clubs. There are tons of wealthy older divorcees and single women around. And also happy hours in exclusive areas.
posted by amberglow at 7:46 PM on February 27, 2005

oh, and highclass shopping areas and their restaurants at lunchtime--Madison Ave, and Rodeo Drive type areas.
posted by amberglow at 7:47 PM on February 27, 2005

It might be worth the investment for your friend to join a high end gym/health club such as the The Sports Club/LA (link to Rockefeller Center location).
posted by mlis at 7:50 PM on February 27, 2005

If you're living in or near an urban area, the local alternative personal ad services are a good route to go hunting for off-the-beaten-path romantic matches. The Stranger personals in Seattle are one such service. Tell your friend to check out the local non-mainstream papers and magazines and see if their ads look promising.
posted by rhiannon at 7:52 PM on February 27, 2005

Craigslist?
posted by kickingtheground at 8:04 PM on February 27, 2005

Isn't this the sort of thing for which one becomes a pool boy?
posted by five fresh fish at 8:29 PM on February 27, 2005

Be sure to read "The Seduction of Peter S" by Lawrence Sanders -- might give you some pointers.
posted by davidmsc at 8:35 PM on February 27, 2005

Isn't this the sort of thing for which one becomes a pool boy?

Or an escort. Or a ballroom dancing instructor.

(Seriously. I hear matronas my mother's age fawning about them all the time.)
posted by Lush at 8:38 PM on February 27, 2005

I was also going to say craigslist. I don't know if it works, but that seems to be where everyone else is trying.
posted by duck at 8:40 PM on February 27, 2005

1) Take a job at a cafe in the right part of town, with the right customer demographic
2) Figure how to, at once, act somewhat gay, yet appear to lust for the older ladies.
3) ?
4) profit
posted by Goofyy at 8:53 PM on February 27, 2005

Job aboard certain kinds of cruise ships might do it.
posted by zadcat at 8:56 PM on February 27, 2005

Adultfriendfinder.com?
posted by timyang at 9:04 PM on February 27, 2005

Become a personal trainer in Greenwich, CT.
posted by xo at 9:26 PM on February 27, 2005

I would approach it like this:

Location: Barnes & Noble, upscale shopping center.
Target: older woman, someone reasonably attractive.

Your character: You are a normal high-testosterone male -- looking get them in bed a couple of times. not looking for a permanent long-term boy/girl relationship. Just looking for as much as you can get.

Be forward, flirtatious - how easily can you get a woman to be interested in you? ... the goal is to get her to have a cup of coffee ... Say "I'm dying for some some caffiene . Do you have time? I'd love to talk to you more about this, would you like to go have a cup a coffee? I'd like to talk to you more about your views on such and such." You get the idea.

Most women that age are very flattered ... if they resist a bit that's because they want to be pushed. What woman wouldn't want to be flatterred. It's ok for them to think you're trying to pick you up. You want them to. "I always find older women attractive."

Goal is to get a phone number. Say "This has been fun - I'd love to take you lunch someday ..." "I've always found older women attractive and you are certainly attractive ... I know you're a little older than me, but you're very attractive and I'll like to stay in touch. Make my day, give me your phone number." Let her know you plan to use this number. set up a lunch.

The overal goal is after seeing them a couple of times to get into an intimate relationship.

You have to be a very comfortable person. If you aren't start talking to people you don't know. Get comfortable talking to strangers and having that under your control. Failures are just as important as successes. The more you do it, the easier it gets.
posted by fourstar at 9:57 PM on February 27, 2005

Response by poster: fourstar, is the small text from a book or an article? Or did you write that yourself?

And the last paragraph could apply to practically anyone- very good advice.
posted by ThePinkSuperhero at 10:25 PM on February 27, 2005 [1 favorite]

PinkSuper: The small part I compiled from notes I wrote down during a conversation that I had with an older woman some time back concerning a similar matter.
posted by fourstar at 11:57 PM on February 27, 2005

get him a MILFhunter.com membership?
posted by matteo at 12:35 AM on February 28, 2005

You sure aren't going to charm her by reminding her over and over that she's an "older woman."
posted by Go, now. Go! at 12:56 AM on February 28, 2005

Buy her the second cheapest bottle of wine at the local wine bar...then ask about her dead husband's suit size...sorry, a friend of mine has a whole comedy act about this.
posted by lackutrol at 1:24 AM on February 28, 2005

Seriously, though, if the guy knows or can learn to play bridge, he's golden.
posted by lackutrol at 1:26 AM on February 28, 2005

Hang at the Sheraton Tara, right by the turnpike in Newton, Mass. I always heard that's a traditional gigolo tryst place.
posted by stupidsexyFlanders at 4:02 AM on February 28, 2005

you could also play clueless shopper at an upscale store--Barneys, Bergdorfs, etc--hold a sweater/try it on and find a woman and ask if she thinks it looks ok...
posted by amberglow at 5:32 AM on February 28, 2005

You are not likely to find these women using the internets. They frequent board rooms, charity balls and upscale fitness centers. Stick with the fitness centers.
posted by caddis at 5:37 AM on February 28, 2005

An upscale gym or pool. A bookstore. My personal favorite: Mid-day shopping at Barneys, Bergdorfs, Neiman Marcus (no malls). Go a bit late, 1:30 - 2:00, when the ladies have already had a white wine or two, but before 4, when they've got to head back to the manse. Find someone to whom you are attracted (or it won't work). Follow and watch a bit when she leaves the cafe. Look bemused, shaggy, curious, confident, in need of a real woman but not needy, and mix all that with a modulated display of respect -- but not too much, you want to keep the chemistry, not become an employee or surrogate kid -- and natural reserve. Strike up a conversation -- that's instinct, you'll have to feel the moment and use what's happening for your material. Watch her body language, for goodness' sakes -- eye contact, hair touching, suppressed smile, very telling. If you're not vibing her interest, ditch the plan, try another day, another woman, do not not not press it. If you are vibing, don't ask her for coffee. Get a number or email address. Wait a day or two and go back in.

No hotel bars, no acting gay, no bridge-playing (??), no cluenessness. Rich women don't read Craigs List looking for boys, ok? And never ever say "I've always been attracted to older women." This makes you sound weirdly dysfunctional, in need of a mom. You can talk about the gap later -- she will certainly bring it up. Approach as a man would a woman under regular circumstances. Be attracted, be authentic. Women know when it's forced or fake. If she's really rich, she probably won't mind your little make-over agenda so much, as long as she feels good with you.

This happened to me five months ago. I'm not rich so there was no agenda, just mad chemistry ... and now we're in deep and true.
posted by thinkpiece at 6:05 AM on February 28, 2005

Where is he located? I've, er, known others who had quite a bit of success romancing older women when they worked as beach lifeguards on 'rich' beaches in Florida.

And when I say success, I mean, being traded amongst older, married women, getting taken on ski vacations, getting the keys to beach houses for months at a time, clothes, food, etc.

There's no dignity in it whatsoever, but the benefits are unstoppable.
posted by saladin at 8:07 AM on February 28, 2005

Response by poster: My friend is in New York City.
posted by ThePinkSuperhero at 8:14 AM on February 28, 2005 [1 favorite]

Is he athletic? There are some seriously 'rich' beaches in the Long Island/New Jersey area that would be prime targets for someone like him. Even if he doesn't become a lifeguard, the beach is a great place to meet bored, rich, married women.
posted by saladin at 8:29 AM on February 28, 2005

I'm really surprised that no one has yet mentioned the opera. The demographic skews older, there are often social gatherings before, after, and at intermission, plus you get to hear some great music.
posted by matildaben at 8:58 AM on February 28, 2005

Maybe your friend could find a nice older woman that he actually likes? Without the profit motive?
posted by Nelson at 8:59 AM on February 28, 2005

Response by poster: Well, when that's the question, that'll be the answer.
posted by ThePinkSuperhero at 9:27 AM on February 28, 2005 [1 favorite]

Exactly what do you mean by "older"? Cause there are lots of ways of being "older" - most having nothing to do with bridge, scrabble or knitting.

Try a sky diving class, or snowboarding. Or get involved with politics and work for a powerful "older" woman. Of course, there are always mountain climbing clubs.
posted by trii at 10:22 AM on February 28, 2005

My neighbor seems to fit the bill: 40-ish, doesn't seem to work yet rotates through different 50K+ cars every few months (2 at a time). The only activity at which she seems to regularly engage is walking her 2 little yippy dogs. Come to think of it, there are two women like this in my neighborhood.

I know there are plenty of dog runs in NYC, maybe he should borrow a dog and see if the rich ladies of NYC walk their own dogs these days.
posted by probablysteve at 11:47 AM on February 28, 2005

Two words: Santa Fe.
posted by gottabefunky at 2:10 PM on February 28, 2005

O.k, so after reading this post my friend set up for me, I decided to join to be able to put in my own thoughts.

I AM attracted to older woman, the 25-39ish range but always open to exceptions... and its not just about profit, I just think that would always be a nice perk on the side.. I am cool with being arm candy for an older mature women. I know there are plenty out there that want someone they can dress, mold, etc etc ...

so I like all of your suggestions, I think I will try a few of them and post back.
posted by crewshell at 3:07 PM on February 28, 2005

Excuse me for choking...errrr it was the "25 to 39"ish range. Good luck on that! Most rich 25 year old women are not interested in younger, poorer men that they have to make over. What you want is someone in the "beginning to fade" range, that is about 35 plus.

And never ever say "I've always been attracted to older women." This makes you sound weirdly dysfunctional, in need of a mom. You can talk about the gap later

IN fact you should take the opposite tack which will you make you sound normal and the woman especially desirable. "I've never been with anyone older, but there is something quite exceptional about you."

For what it's worth: I'm 11 years older than my husband. Sadly I am not wealthy. So it is possible to be attracted to an older woman without the sugarmomma effect.
posted by Secret Life of Gravy at 5:19 PM on February 28, 2005

I AM attracted to older woman, the 25-39ish range...

crewshell, exactly how old are you?

What you want is someone in the "beginning to fade" range, that is about 35 plus.

I second this notion of the gravy, but might even push it over 40.

I would suggest some research into the mentality of the ladies you wish to woo as well. Read the wo-manifestos of 60s and 70s to get a better idea of the philosophical makeup of your conquests. The Feminine Mystique is a classic, but combine that with the other end of the spectrum like The New Housekeeping: Efficiency Studies in Home Management.

Also read all of Oprah's book club books. Try other less skill-intensive hobbies than Bridge (which is rather complicated and if you're not a decent player you'd better charm that millionaire heptagenarian who is east.) Do crossword puzzles. Get into antiquing.

Best of luck.
posted by frecklefaerie at 11:10 PM on February 28, 2005

Response by poster: Crewshell is 20, almost 21.
posted by ThePinkSuperhero at 6:47 AM on March 1, 2005 [1 favorite]