“Where Can I Find a Decent, Much Younger Woman?”

I am asking for an idea, not bullshit. I have never been married. I don’t smoke or drink alcohol — both really stupid habits — and it’s hard to meet really DECENT women. I am over 45, but I won’t waste my time trying to date women my age. A friend suggested a particular dating app — well, its filled with losers!! I am financially very well-off. I like really polite women. Not many of them left either. So, dating expert: I would like to meet a woman who is really interesting, between 30 to 35 — someone with a life! I will pay to meet you in person if you can help me find someone! Wendy, let’s talk. If you want my cell number, just ask. — Looking for a Polite, DECENT Woman

The real waste of time isn’t pursuing women your own age — although I can certainly appreciate that you’ve likely had bad luck with women who have enough experience to sniff out the bullshit very quickly; the real waste of time is being so rigid in your expectations. It’s laughable that you think women 10-15 years younger than you should even be interested in you, period, but you want someone polite and decent and really interesting on top of it? Come on, women don’t have to be polite and decent and put up with the bullshit of guys like you.

Look, I know old farts still think it’s charming enough to be “financially very well-off” to attract the ladies, but if you want quality women, you’ve got to bring a lot more than a fat wallet to the table. For one thing, modern women are doing pretty well themselves and, in general, aren’t looking for sugar daddies. Besides an extra 10-15+ years of baggage, what else can you offer? If you want someone so much younger, who is going to be in high demand, you gotta hit some high notes yourself.

I have been married for 25 years. My wife doesn’t want me to go to her son’s house for Thanksgiving. He lives in a big house and has money. My wife thinks I am not good enough to be around them or the rest of her family. I am a Christian chaplain with Chaplain International and a retired auto worker and Vietnam veteran (combat Navy). I don’t do anything wrong. I am going to divorce her. What do you think? — Unwelcome Chaplain

I think that after 25 years with your wife, you should have a pretty good sense of where you stand with her and if spending Thanksgiving without you in a home where you aren’t welcome is a reflection of her feelings and her loyalty for you – and it seems it is — divorce is probably a good option for you. In the meantime, maybe you can volunteer your services this Thanksgiving? I’m sure there are plenty of people who’d welcome a chaplain’s kindness and compassion if you have any to spare this year.

My ex-wife and I have been divorced for five years now. We are able to co-parent well the majority of the time. Outside of our children, we tend to butt heads due to past trauma caused by me. I recently took my two children, thirteen and eight, to meet my girlfriend of two years for the first time. Yes, it is a long-distance relationship at the moment. Two weeks before our trip my ex-wife and I had a nasty argument, were disrespectful, and things were said between the two of us. While on vacation that is going perfectly at a beautiful location, I want my ex-wife to be here sharing this experience with me instead of my current girlfriend. I personally have not ever felt an emotion like this that has come to consume me. Any insight on what may be going on? — Missing the Ex

I wouldn’t necessarily view this sudden feeling, which has immediately come to consume you, as a reflection of your true feelings for your ex-wife, but I would definitely reconsider where things stand with your current girlfriend and whether you are capable at this time to maintain a healthy relationship. If you’re someone who has a history of creating drama and butting heads with a partner, it may be that you simply don’t know how to just be when things are “going perfectly.” And what better way to stir up some dramz than to feel suddenly and immediately consumed by thoughts of an ex you were recently having nasty arguments with? I say hit the pause button on your relationship, step back, and get yourself into some intensive therapy.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. LW1- First step is to get that massive chip off your shoulder. You are not entitled to a partner just because you are well off. Women on dating sites are not “losers”, they are literally doing the same thing you are. If your expectations are too high then it is time to adjust them rather than dismiss all the women you come into contact with. As an educated women in my mid-30s I am completely put off by your letter. You come across as entitled, aggressive, and misogynistic.

    LW2- I am sorry to hear about your situation. Is this something that has recently changed between you and your wife or has she always been dismissive of your accomplishments? If this is new and your marriage has been good, I would seek out counseling before tossing away more than two decade marriage. If she has always felt that your financial worth is a measure of your self worth then the marriage might be over.

    LW3- Is this the first vacation you have taken with your children post divorce? You say that you caused the trauma that ended your marriage, have you worked through what happened with a professional therapist? It is possible you are still coming to terms with the demise of your marriage and your role in it. I agree with Wendy regarding your need to find the root of your destructive tendencies.

  2. LW1: a good start would be to stop considering dating like a transaction. How can you be surprised by an individual who has a charm, with whom you can connect, if you are so rigid in your judgements and so focused on the ideal product you are ready to “pay for”? Be realistic and start dating women round your age. You will have objectively much more chances to relate if you are open-minded and if you give a chance to a process between two individuals at the same period of life. But perhaps you don’t really want to meet someone? Do you?

  3. How is LW1 not Robert?!?!

    1. Nah, Robert may be extremely rigid with wildly impossible standards, but he isn’t a d*ck about it. This guy, however…

  4. Ooh boy, LW1, you read the room badly.

  5. Carolina Blue says:

    Wendy, that LW1 response is gold. You’ve made my Monday, far and away.

  6. LW1: NEWSFLASH: Polite, decent women like polite, decent men. You are neither. (H/T to BGM.)

    LW2: If you’re asking for permission to divorce your wife, you’ve got mine.

  7. Avatar photo Skyblossom says:

    LW1 I have so many questions. How do you define decent? Do you mean a moral person or a person who goes to church or a person who doesn’t go to church or is it a woman who can support herself. Is it a woman who is kind and thoughtful or is it a woman who will do what you tell her to do? Then I get to your next statement where you consider women your age a waste of time? Why would a woman of your age be a waste of time? Really, why is your contemporary a waste of time? If you don’t like that age why would a younger woman like that age meaning why would she like that age in you? How well off is very well off and why do you think women should want you just for that? What good is a bunch of money if it comes with a bad attitude?

    Besides your income what do you have to offer? Are you kind? Thoughtful? Fun? Do you cook and clean? Are you good at listening and compromising?

    If you want a really interesting woman you will have to be a really interesting man. Are you? Do you do interesting things? Go interesting places?

    All you can say about yourself is that you don’t smoke or drink and that you make a good income. That’s it. Nothing about you being an interesting person. You also show yourself to be judgemental. You consider women your age a waste of time. You consider smokers and drinkers to be stupid. You consider Zoosk to be stupid. You also say that the vast majority of women aren’t polite. What do you consider really polite? All of your criticisms in your one paragraph show that you aren’t polite yourself.

    If you want a really interesting really polite woman you have to be a really interesting really polite man. You also need to be flexible enough to meld two different lives together and kind enough to not be hugely judgemental.

    1. golfer.gal says:

      I have a feeling “decent” is defined in this instance as cultured, well educated, polite, amenable, and Christian. Read: deferential to her partner, has a good job and lots of education and yet is wowed by some old guy’s moderate amount of money, is super hot herself but turned on by men who could be her dad’s age, and wants to spend her time making said old guy feel super special by laughing at all his jokes and finding him the most fascinating person in the room. Because, money.

    2. Avatar photo Skyblossom says:

      I’m guessing polite and interesting means likes everything I do and say and doesn’t mind that I’m much closer in age to her dad than to her. She will be way too polite to point out that she has her own interests and wants and needs and doesn’t want to be with an old man.

      She will be way too decent to write off all men in his age range even though he is writing off all women in his age range. He can be as hypocritical as he wants but she won’t be.

  8. Ah, it’s been a long time since I’ve been here. I’m happy to see things are going well.

    LW1: I’m replying to your letter because I’m probably the only one here who is both male and maybe even older than you (“over 45” could mean you’re 95, for all I know). Old man to old man, here’s what I think: you’re looking for a young piece of ass that isn’t so young that you can’t understand what she’s saying to you. You want her to be polite because you don’t really want to have to be held accountable or to have to listen to her. You are willing to fly to Wendy because… what? Maybe you think your opulence will impress her? I’m not clear on that one. Seems sort of stalker-y to me. So here’s my advice: hire escorts. You can afford them. You can pick the age. You can tell them to be polite, and they’ll gladly accept your money as they act as you’d like. I’m not seeing the downside of this for you.

    Or maybe I’m misreading you, and maybe, despite your healthy and wealthy lifestyle, you’re not quite able to get across your true intent here. Perhaps your financial well-being comes as a result of doing nothing but working hard in isolation for decades, missing out on crucial social-skill training because you’re very self-conscious and afraid of conflict (hence the need for women to be “polite”). Maybe that’s why your letter reads like it was written by a jackass. In that case, it’s not really your fault, but pay someone to proofread these for you in the future. Maybe your real reason for wanting someone 30-35 isn’t because you’re just looking for sex (which, by the way, is better depending on the person, not on their age) but instead wanting to convert your wealth into a happy, supported family, and so you want someone with whom you can develop a relationship that blossoms into true love before the age-based risks of pregnancy grow too high for you to have the five kids you wish to dote on.

    But… I don’t think that’s the case.

      1. Hey there! I’ll need to get caught up, but it feels good to drop by again. I’m glad that some regulars from the distant past are still here – hey there, @Bittergaymark!

      2. Well, it’s nice to see your name pop up again. There are still a lot of old regulars hanging around, BGM included. 🙂

      3. Bittergaymark says:

        Hidy ho, _jsw_!!

  9. Bittergaymark says:

    LW1). Yikes. Please tell me You are trolling with this post! I think you need to probably accept that you are going to remain single forever as You insist on something that does NOT exist. Not for YOU anyway…

    LW2). Is there more to this story? Or is Your wife just plain awful? Honestly? I can’t tell…

    LW3). Yeah. You need to end things with the new GF as you clearly just aren’t that into her.

  10. Anonymous says:

    LW2 — Are you absolutely sure your wife’s reluctance to have you at her son’s house is due to money? Have you been left out for the last 25 years, or is this a new thing? Given that she’s been married to you all this time, I can’t imagine that, all of the sudden, your lack of material wealth is an issue when it wasn’t before. If that’s def the case, then you’re probably right that your marriage isn’t working.

    I’m sorry you’re feeling judged and left out…but it’s hard to believe that it’s just this one single thing that has you contemplating divorce.

    If being left out is a new development, maybe some self-reflection is in order. Have your interactions with her son and extended family changed? Are you arguing about politics or moral issues? With the current administration in the White House, a lot of ugliness is out in the open that used to be hidden away…maybe your wife is trying to keep the peace.

    Are there alcohol or substance abuse problems that have become worse? Has your wife expressed concerns about your behavior that you’ve been unwilling to address?

    You mention that you’re a Christian chaplain…does your wife’s son share your faith background? If not, do you make a point of evangelizing at family gatherings? What may feel innocuous to you, leading grace at dinner, for example, might seem pushy to those who don’t share your beliefs.

    Just spitballing. I have no idea whether your wife has just decided you’re “not good enough” to be around her son’s family or whether there’s more to the story. But I agree with Wendy that volunteering on Thanksgiving is a great way to help others while avoiding feeling lonely and resentful.


    1. These are all great questions. As a former chaplain myself, there seems to be more to this story than just not having money. It sounds as if something has changed. Is he proselytizing over the Brussels sprouts? Is someone struggling with substance abuse? Is she just worried that the letter writer might have Covid or get it?

      Divorcing your wife over one holiday does seem a bit extreme.

  11. Avatar photo Skyblossom says:

    LW1 If no women will date you the one thing in common among you and all those women is you. You aren’t presenting yourself as someone they want to meet. If you can’t make yourself desirable Wendy isn’t going to be able to do that for you. She can give you advice but you have to be someone women want to meet.

    If you want to meet interesting women you need to go to activities that interest you. There you will find interesting women. Many of them will already be coupled up but some of them won’t be. Many of them won’t be in your desired age range. That’s okay because you aren’t in their desired age range either.

    You don’t seem to understand that women get to have their own opinions about which guys are a waste of their time. Most of the women in the age range you want are going to decide your age makes you a waste of their time. That’s their right. You get to have your wants and must haves and so do they. You get to turn down women your age and younger women get to turn you down for your age.

    My husband is 6 weeks older than me and I like it. I never wanted to date an older man. I definitely didn’t want to be married to one. My grandmother was a widow when I was born and she was alone through my entire childhood. I didn’t want that for myself. I wanted a lifetime partner, not half of a lifetime partner. We have similar childhood memories. We both watched the first lunar landing live. We went to school at the same time. We both remember the hippie era. We were both in college when the space shuttle Challenger blew up. We have the same cultural references because we grew up at the same time, even if it was on different continents. I like having that in common. I like that we will hit our retirement years at the same time. I like that I’m not 57 taking care of a sick old man. There is no way I would have dated your equivalent when I was 30.

    1. Sea witch says:

      My partner is a lot older than me, but the difference between him and the first LW is that he’s not a raging glassbowl. We have enough in common to enjoy each other’s company.

  12. Avatar photo Skyblossom says:

    Concise question

    How do I get polite, decent, interesting young women to trade their youth for my money?


    It’s stupid to trade youth for money so you should go back to Zoosk.

  13. katmich15 says:

    LW1, here’s your problem. You are looking for a quality, interesting, 30-35 year old woman, but quality, interesting women don’t date older men for their money, so you are going to attract the opposite kind.

  14. I want to echo Skyblossom’s sentiment about shared experience. My partner and I are only two years apart, and I love being able to make a reference to some silly cartoon that was on when we were kids, or that he remembers mixtapes, life as a teenager before 9-11, the rise of cell phones and having to hit the “8” button four times to text a freaking “t.” We have the same relationship with the world because we experienced similar things. I couldn’t get that with someone ten years my junior and someone ten years my senior would’ve experienced it differently.

  15. LW 1 – as someone in your dating age range all I can say is yikes! now, LW, you and I are sadly not meant to be because I am a mouthy, independent woman who is probably more interested in one of those losers on Zoosk. You are one big red flag, your contempt for women is so intense, you think nothing of them. They are objects to you and that shows. You are not good partner material, your views on partnership are quite frankly gross. Money comes and goes, but your personality is quite frankly garbage. You need therapy.

    LW 2 – Thank you for your military service. Please divorce this woman, anyone who thinks someone is ‘not good enough’ to be a part of your family is not worth your time. You deserve to be cherished, please go find that.

    LW 3 – Maybe you aren’t ready for this step. It’s ok to need more time to heal after a divorce. Also please also consider therapy to help process what you are feeling.

  16. LW1 – Your note should have been worded better. However, I will say this. The woman you want will not be online. She is too busy out doing stuff. So if you want someone nice and fun and has a life, she is too busy having a life to be on online dating sites. If you want to be meeting this kind of woman, you need to be out too. You want someone polite and cultured, join a golf club and start doing mixed golf outings. Find friends to go to wine tastings or join a mixed doubles tennis league. If you want traditional morals, go to a mega church and start joining clubs in the church or start volunteering with under privileged kids or an animal shelter. If you want someone adventurous, join hiking groups, ski groups, salsa lessons, or take trapeze lessons. If you want to find a woman who would be a good homemaker, join a cake design class. You want a professional, start attending industry technical events. I would say to find a woman that you want to be around, build a life that she would want to be in. But it isn’t like placing an online order and getting two day shipping and she will arrive.

    1. Sea witch says:

      Wine tasting is a no-go for this guy. Alcohol is among all the other things he strongly disapproves of.

  17. If this LW isn’t Robert, he’s Robert a year from now after he finds an on-line incel site. Lots of luck finding such a woman.

  18. Sea witch says:

    I’m going to guess that LW1 means “does as she’s told and doesn’t answer back or give me any lip” when he says he wants a “polite” woman.
    As for DECENT – does that mean “virgin”? Good luck finding a 30-35 year old virgin, dude.

  19. LW1, your letter oozes contempt for women. My advice is to start going weekly to therapy and try to work on having a better attitude and being a kinder person. You need to fix yourself before anyone is going to be interested in you.

  20. dinoceros says:

    LW1: Not gonna happen.
    LW2: Why have you been married to her for 25 years? That part is on you.
    LW3: Like Wendy said, I think the real issue is you realizing you’re not that into your girlfriend. Leave your ex alone. If you pursue whatever feelings you think you have, you’ll ruin the peace you’ve created as co-parents.

  21. They should just answer the question not blast Trump out of the blue. The guy could very well be a Democrat piece of trash anyway and that was nonsensical and irrelevant. Funny I can pretty much promise the sugar babies and escorts this guy will attract will not be fans of Trump.

  22. LMFAO. I would act nice and polite for 2 yrs commitment, but only after 150k is deposited in my account!

  23. LW1… just go back to the prostitutes you’re used to. Also, I’m almost positive he’s not a trumptard sounds more like a Biden supporter… (see how that works? They’re all idiots) no need for politics in here, they’re all lying rich entitled Aholes
    LW2… what are you waiting For?
    LW3… you cheated on your wife ruined your marriage now you want to ruin you’re girlfriend. I’m glad you’re not my dad. Men like you are why women are stressed out. Just stay alone with your self try that for a while

  24. mellanthe says:

    LW1: Preferably? Don’t. It’s creepy. Unless a woman’s dating profile explicitly states she’s happy to date older men in her age preferences, leave her be. As a woman in my 30s, when I was online dating I was inundated by men in their 50s or 60s ( my dad’s age, for crying out loud) who clearly ignored my age prefernces and sent me creepy messages about how young I was.

    Realistically, most women half your age aren’t looking for someone twice their age when they get plenty of attention from men in a similar stage in their lives who are more likely to match what they want. Look at women your own age, see them as people, and stop assuming the worst of every woman you see on a dating site. Before you start demanding some super young, attractive, polite woman (insert whatever unrealistic list you have here) stop to ask yourself what you could offer these women apart from money. Be realistic about yourself and don’t be quick to discount anyone who isn’t a supermodel.

    LW2: You should know if you’re happy with your wife, if she loves you and you love her, and if you feel like a part of the family. Nobody else can tell you if divorce is the right option.

    LW3: You have a complicated past with your ex and don’t get on. It didn’t work out, and it sounds like you hurt her a lot, so it’s unlikely she’ll want to restart a relationship with you, or that it will work after all that trauma. You may crave her instead of your current GF, but could that be mroe indicative of problems in your current relationship? It sounds like you need to work on that and see what might be causing these conflicting feelings.

  25. Ok that Robert link sent me back down memory lane to catch up on that thread and I am crying laughing at this post from Kate:

    “I cringe when I see women wearing that work outfit that’s like, dress pants and a button down shirt that was what you wore to your first job 20 years ago. Like the pants were kind of bootcut, and the shirt untucked. Now you’d wear a higher waisted, slim straight pant, even dark jeans, and a tucked-in shirt and some kind of jacket or sweater. Times change.”

    Because I literally just cleaned out my closet and found all those Express button down shirts and boot cut slacks that I haven’t worn in at least 5 years. Nailed it.

  26. Carol Hill says:

    LW1. Thank you, Wendy, for this delicious answer!!!!

  27. LW1: Go somewhere and pay a woman who meets your criteria to be your girlfriend then use cognitive dissonance to convince yourself she is a “decent woman.” That is the ONLY way YOU are going to get what you want. /s (well not the /s on the part of him not being able to get what he wants.. he is gross)

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