“How Do I Ask My Much Younger Boyfriend to Propose to Me?”
Five years ago, after a somewhat acrimonious divorce, I went on a weekend celebratory trip to a nearby city with my closest girlfriend. We ended up in a trendy bar and, after a few glasses of wine, I got fixated on a particularly handsome younger man. We got to talking and I couldn’t stop laughing at his humor. He was smart, funny, and seemed smitten by me, and I ended up spending the night with him in his flat by the seaside. I woke up the next day and looked at that same man bringing me coffee in bed and realized he was younger than my eldest daughter.
I haven’t stopped seeing him. I’ve always thought it was a temporary thing. He is now 28 and I am 48. I believe in ageing naturally, and thanks to genetics, I am slim and athletic and look younger than I am, but my hair is now silver and nobody would ever mistake me for a contemporary of my boyfriend. That has posed problems for him with his friends, and particularly for the wives and girlfriends of his male friends, who seem to think he is wasting his youth on an older woman.
I have always kept strict boundaries in our relationship. I’ve told him throughout the years there is no future for us. I don’t let him visit me. I spend three to four days a week with him. I have had other relationships during this time that I have not been honest with him about. I know he has never been unfaithful to me. I have never made even a cup of tea for him. He caters to my every need and pays for every dinner out and every holiday we take together. He is still strikingly handsome, and he is very successful in life.
Something has changed in the last month in our relationship. We went on vacation where I befriended a 62-year-old German woman who is everything I want to be when I reach her age. She is beautiful, confident, and intelligent, and she’s lived an interesting life and has taken risks that I never would have considered taking. On our last day on the island, she told me I was a fool for not marrying the man who so obviously adores me. That seminal moment changed my entire thinking about my relationship, and now I want to commit to him and for him to commit to me.
How do I tell my boyfriend, after five years of saying we have no future together, that now I would like him to propose to me? — Ready To Commit
I think you should propose to him! Or, at the very least, tell the man, after five years of keeping strict boundaries and saying you have no future together, that you have realized what you were too stubborn or afraid to accept sooner: You love him. That’s if you do, actually, love him. Do you? Or do you just like being loved and adored by him and having all your needs catered to by him? There’s a difference. And while people have married and continue to marry for so many reasons beyond or besides love, it would be unfair to enter a marital union under false pretenses.
If, after being honest with yourself about your motivations, you are sure you love this man, your next step should be to share your feelings. And the next step after that should be showing him how you are going to match the love he shows you. So far, your relationship has been pretty one-sided, with him doing most if not all of the expressions of love and adoration and you doing all of the receiving while carefully guarding your heart. How would things change or deepen between you if you allowed yourself to be vulnerable – to give instead of just receive? I think you owe it to yourself and to him to find out.
You say you were inspired by the older woman you met on vacation in part because she’s confident and interesting and takes risks you’ve never considered taking. Well, you have the opportunity to take a risk simply by finally opening your heart to your boyfriend and letting him in. You can take a risk by telling him you want your future to forever include him. To be emotionally vulnerable with someone you care about is a risk with beautiful potential gains. Taking this risk would begin to even out the power dynamic in your relationship, and if part of your attraction to your boyfriend is the power you have over him, you both deserve to see what might develop once you give up some of that power. The big question you have to answer for yourself first is: are you willing to do that?
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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.
Jeez, bit rough after years of playing the field to suddenly decide you want to lock him down. It’s one thing to not want to commit, it’s another to have other relationships that you weren’t honest about (does that mean there was discussion of these relationships and you lied to save your own skin?).
This relationship really has been all on your terms so far. I hope that if you make a go of it, you can start with an entirely clean slate and the willingness to prioritise him as he has you. It’s easy to say you didn’t in order to protect him from getting attached but it was also awfully convenient and easy for you, wasn’t it?
You have had relationships on the side you haven’t told him about. Why? That’s not cool. I hope you’re using protection. The only reason you seem to want to marry him is because your vacation girl crush said you’re crazy not to. You seem to meet a lot of people on vacation! I don’t think you want to marry him or settle down. Go find your girl crush and sail off to Greece or something.
What kind of woman has a multi-year relationship with a man twenty years younger than herself? Very likely a beautiful and very self-confident person. The same could be said for a young man who could care less what his friends think. You should propose to him. As far as your past infacilities, perhaps be honest and admit to yourself and your husband to be that you are never going to be completely faithful and that is just another thing that makes you special and will keep your soul mate on his toes throughout your marriage.
I imagine ‘Ready to Commit’ is indeed a beautiful woman entirely comfortable with herself and she deserves a handsome, younger husband. Beautiful women are far more likely to have affairs, that just goes with the territory when a man commits to an exciting woman. The only problem I foresee is a horrendous reaction from her children but they’ll eventually get over that.
When I first started reading this, I had the same thought as Wendy “ask him!” but then I kept reading. Holy sh*t. This isn’t a healthy relationship and it definitely isn’t a basis for marriage. Marriage is a partnership based on honesty. What you’re offering is a bad deal on a used car. By your own admission,
you’ve lied to him,
cheated on him,
don’t allow him in your home,
and “have never made even a cup of tea for him”.
Don’t even get me started on the whole, ‘I’ve never contributed a dime to the relationship’ aspect. It completely tracks with the emotional selfishness btw.
This isn’t about boundaries, it’s about control. The question you need to be asking “isn’t how do I get him to propose?”, it’s “why do I have such a need to control this relationship?” I suspect that the fact that he is 20 years your junior isn’t accidental.
If a man had written this we’d be blasting him to tiny pieces on the other side of the galaxy. The dynamics don’t change just because a woman wrote it.
George and Barry: WTF?!?! I strongly suspect that this is the letter writer and her own romanticized version of herself says A LOT about who she is. She isn’t the free-spirited heroine in a Harlequin novel. She’s just……sad.
I agree with everything Part-time Lurker wrote – want to add;
Since OP has never allowed him to visit her, how does she plan to tell her family about this surprise fiancee?
Has she even thought about the logistics of marriage? They live in different cities – who is moving where? Does she expect him to give up his career and friends to move to her? Is she willing to support him while he re-establishes himself in her city? Because, from her words, I don’t expect her to move to his city.
She was heavily impressed by the woman she met on holiday and thinks that marrying her lover will give her the air of being an interesting, risk-taking woman. I think she enjoys the attention (and money) he lavishes on her. I think she is seeing her future as she nears 50 and has realized she maybe doesn’t have any other prospects that will treat her a he does.
I understand her. When I was in my 40s and dating I was approached by younger men. Oh, the ego boost! They were fit and attractive and such a delight compared to the stodgy 50 something men that approached me. But they were flights of fancy, amusing to speak with and pretty to look at, but there were inherent incompatibilities due to age and I was mature enough not to take advantage of them.
I think she is being unfair to her young lover. At some point, she needs to realize that she is doing him an injustice and let him go.
Agree with you completely. He deserves better.
I would be interested to know, if she had never met this amazing German woman on vacation and had that conversation, would she ever had entertained the thought of marrying this guy? Would she have come to this realization herself? It seems odd to me that it takes someone who is a “goal” to this woman to convince her of something that she should have already convinced herself of.
Chances are, when he first tastes her tea or cooking he’ll run a mile anyway
Why is everyone hating on this woman? I love women who are confident and a little selfish. Men love to spoil women like this and, obviously, some women like to be spoiled. I guarantee you that if she asked this lucky guy to wed her and he’d say yes in a second and forgive her instantly for past and future indiscretions. He’s a lucky man regardless of all the slut shaming that is going on. Get over it. She doesn’t have to live by your rules. She can make her own.
Some men are attracted to broken or toxic women, good luck with that Charles…
I love how Wendy engages with letter writers, and homes in on the underlying issues, all the while not being judgmental—because that’s not helpful to the letter writer. When we meet someone further along the path we sense we ourselves are on, it gives a chance to reflect on how what we do today will contribute to the future we would like to imagine for ourselves. In parenting, intimate relationships, or wellness, I’ve been influenced this way. Cynically, though, especially if genders were reversed, it would seem LW is trying to lockdown someone to be there for HER aging process.
I really appreciate your perspective – thank you.
If you take some time and look at it from the letter writer’s perspective you can understand that she kept the relationship distant because it would have shocked friends and family where she lives. I don’t believe you can have a relationship for five years and see someone four days a week without love being involved. She just had to meet someone who encouraged her to grasp what she’s really wanted. I can say, as a young guy myself, women are most beautiful in the forties, fifties and even sixties and they are fun to be with and intelligent and wordly to boot. I have never dated a woman my own age. The guy she is with is very lucky to have found her. As far as her affairs, maybe they will stop and maybe not but they aren’t as earth shatteringly important as everyone seems to think.
Hey: George, Barry, Charles, and Jurgen: I dont think it’s necessary to see your IP address to figure out what’s going on here, but just so you know, I *can* actually see your IP address, fyi.
Oh dear. I do hope it’s not the LW….really defeats the purpose of writing in for your advice.
This advice would make sense to me for a healthy relationship that the person has just had trouble committing to. But trying to turn this hot mess into a marriage right away sounds like a terrible idea to me. Turn the relationship around *first*: Acknowledge that you haven’t been taking the relationship seriously, but would like to change that. Practice honesty and mutual care, get to know each other’s families and communities, spend more day-to-day life together. If you both feel like that shift creates something healthy and powerful, THEN maybe talk about marriage?
This is exactly how I met my first disastrous divorce 🤣 so in short don’t even go there
You’re wrong.
I have a letter Wendy responded to with name calling a few years ago and it’ll prolly fit the cancel culture nowadays. Let me know if you guys want to see it 😄
I don’t know who you are or who or what you’re even responding to here, but I remember very clearly all the times people tried to cancel me, and thirteen years later I’m still here.