My Boyfriend of 5 Years Hasn’t Proposed to Me Yet. What Should I Do?

man in black suit proposing to a woman giving her an engagement ring


I’m 42 years old and my boyfriend is almost 48. He was married once before and has two young adult children. We’ve been together for five years. Three years in, I asked about marriage and he told me he wasn’t ready. I was ready to break up with him until he gave me a sweet promise ring and swore that he really does want to marry me, but he just wasn’t ready and needed more time. He convinced me to wait because he swears he wants to build a life with me.

I’ve read your advice about allowing him to choose me, so I didn’t bring it up again for almost two years. I finally started to wonder and asked him about it again, only for him to tell me the exact same thing: that he’s not ready, but he wants to marry me someday and he sees a future with me. Problem is: he won’t give me a timeline, he won’t say why he’s not ready, and he wants us to live together first.

We own our own homes and the housing market is highly overinflated where we live – so much that we can’t afford to buy a house together. So, there’s no chance of us living together anytime soon. Plus, I’m not sure that living together as a “trial run” is the best way to approach marriage. If he’s not interested in marrying me now, I’m not sure that living together will change that.

He swears that he really does want to build a life with me, but I’m not sure I can wait another few years for a man who continues to kick the marriage can down the road — and the “living together trial run” seems like an excuse to prolong the marriage issue. I wish I could just break up with him, but I stay around because he keeps saying he really does want to marry me, but he’s just not ready and wants to live together first.

He is really good to me and we get along outside of this issue. We have fun together, laugh, and he’s always doing nice, thoughtful things for me, like fixing things in my house and buying me little presents. But, I’m starting to become disenchanted with the relationship because I don’t want to be his girlfriend forever. I don’t know if I should stay or go.

Thank you for taking the time to read this question, because I know you receive thousands of them.


Dear Jessica,

Thanks for the kind words and the all-too-familiar story.

Sadly, I don’t think there’s much I can add to it.

I could throw around stats that say that people who wait over five years to get married are more likely to break up (because one party never wanted to get married in the first place).

The fact that he hasn’t married you means that he doesn’t want to marry you.

I could throw around an EMK aphorism that “men do want they want.” In other words, if he wanted to marry you, he already would have married you. The fact that he hasn’t married you means that he doesn’t want to marry you.

I could point out that you shouldn’t have to put a gun to a man’s head to get him to propose. If he has to do it under duress, it’s not the ideal start for your marriage.

I could implore you to ask him, point-blank, why he’s so afraid of marriage and what’s holding him up. Who knows? Maybe you’ll learn something and maybe he’ll have a revelation that his fear is irrational and that, for all intents and purposes, you ARE married.

But, since you sound like smart woman who has had plenty of time to think about this, I’m going to assume you know all of that, my friend.

So let me give you validation of your worst suspicions: your boyfriend has played you.

Not because he’s an evil guy, but because, like most of us, he’s operating out of his own self-interest.

His self-interest is to keep you as a girlfriend and not to get married. And he’s done a brilliant job of that, what with the promise ring and the two years(!) of silence and the living together excuse and the lack of a timeline to head to the altar.

It’s all bullshit, Jessica.

And since I’m not emotionally invested in this the way you are, I’m going to give you the ultimatum that you should have given to him two years ago.

Either decide that you’re content being his permanent girlfriend (but not his wife) or break up with him and find a guy who wants to marry you.

The only thing you CAN’T do is keep on waiting for a guy who doesn’t want to marry you to step up and marry you.

I wish you the best of luck.

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  1. 1

    I just don’t get it…Marriage is irrelevant in the modern era…You donot have the government legislating your friendships, why should it legislate your romantic relationships?It’s a piece of paper to put you in a certain tax bracket….Marriage became irrelevant the day (decade?) religion became irrelevant..The genie is out of the bottle…People will never ever go back to fill up the churches, and men are never ever going to be marriage minded anymore…the sooner we gulp down this blackpill, the better will it be for our sanity

    1. 1.1

      Juggernaut_The_Celibate, there are so many people that would disagree with you. Marriage has not become irrelevant, it merely changed and adapted to the modern age. There are many people, myself included, that view marriage as the ultimate commitment you can make to your partner and it’s the foundation of building a life together. Saying “men are never ever going to be marriage minded anymore” is a grossly negative and untrue statement for many men. However, if you go through life with that mindset, you surely won’t find any hope for marriage. Perhaps your negative thinking has obscured your view of the modern world.

      1. 1.1.1

        Thank you for your reply …I am sorry if it has caused any distress..But the rate at which young men from the Generation Z,and younger Millenial men are secretly embracing ideas that are not really entertained in polite conversation is simply it Red Pill, Black Pill, Alt-Right among whites, pride in some of their own medieval violent empires among many non-whites (some modern Turkish men being prime examples) etc…….Have you seen the view rates and comments on anti-marriage videos on Youtube?…All this just plain points to the fact that there is colossal civilizational level discontent among the under 40 crowd regarding inter gender relationships and dynamics…feel free to disagree though, but I would be eager to know your counter arguments

        1. Evan Marc Katz

          Yes, JTC, there are a lot of sad, angry, frustrated men who lack empathy, confidence and social skills and are rebelling against marriage. They can go their own way. This blog is for people who want relationships. If you don’t, there’s not much reason for you to be on a dating advice blog for women who want commitment.

  2. 2
    Emily, to

    So let me give you validation of your worst suspicions: your boyfriend has played you. … His self-interest is to keep you as a girlfriend and not to get married.  
    Yep. He’s given her lines of b.s. to keep her around. It’s extremely selfish. Read the boards on These stories of   being placated with “We’ll be engaged by the end of this year” … as the years pass by are all too common.

  3. 3
    Dog Mom

    Why does marriage have to be the end goal? Why can’t having a great relationship be the goal? He’s been married. He wasn’t good at it. He loves her. He treats her well. He’s thoughtful. He’s fun. I’d say that’s pretty terrific. It’s more than a lot of married women can say.

    1. 3.1
      Evan Marc Katz

      It doesn’t matter if you want to get married. The OP does. That’s all that matters. Their goals are misaligned. Just like one partner wanting kids and the other not wanting kids. Neither of them is “wrong”; it’s just not an organic match. There’s no reason she should stay in a relationship where she doesn’t get her desire of being married met.

  4. 4

    I don’t buy that it’s all because he wants her as his girlfriend but not wife. Certainly that’s part of the equation but he could have just said it so and even then, plenty of women would accept that if they are satisfied, some with often futile plans to change his mind. He’s probably not being honest to himself either, likely he thinks he is supposed to want marriage but he doesn’t so that’s a way for him to alleviate his guilt over that. Then there’s his previous marriage, we don’t know under which circumstances it ended but it could have altered his perspective negatively, fearing that he would go through it again. His promise ring shows this possibility, maybe in normal circumstances he would have wanted to marry her but fear impedes him. It’s likely that a good talk about that is in order. What he thinks about future with her, how he feels about the prospect of living together and how he differentiates between that and marriage etc. You are together for 5 years, surely he would have something to say about these questions. You should kindly and directly ask them in a conversation. It seems the more he gets near it, the more afraid he become from the promise ring. Highlight what he thinks and see how you can mutually get your needs.

  5. 5

    Hi Evan, I absolutely agree. No one can push a man who doesn’t want to get married. I believe I am a victim of this you were communicating with me before as to whatever happened to a wonderful relationship I used to have.   My ex boyfriend stated that to him, living together is already a lifetime commitment. I don’t know why since we lived together in 2012 I met him in 2010, he knows that I believe a man should propose and ask for marriage and I definitely will not ask but waited until we got engaged in 2016 but never married. So I decided to move on and moved out of State a couple of years ago. We’re good as friends and I visited him every time I can. I am no longer wearing the engagement ring he gave me and he doesn’t ask about it. Although he said I’m everything to him I just lost interest. Besides he seems to have stopped living meaning doesn’t want to do anything but drink himself to death, smoke and sleep.


  6. 6

    “Not because he’s an evil guy, but because, like most of us, he’s operating out of his own self-interest.”

    Are ‘evil’ and ‘operating out of his own self-interest’ the only options we have here?   Seems like black and white thinking to me.

    1. 6.1

      Yes, that’s what I pointed out in my comment too. He could have various reasons to do that. Even if he’s operating out of his own self-interest, there’s a reason why he perceives it as in his interest.

  7. 7

    Evans advice reminds me of a time when I was having CBT, and I was expressing frustration for the third time about the fact my two ‘problem solving’ attempts about a relationship issue were rejected by my partner. I was desperate to solve it and he just couldn’t see the issue.

    My therapist cut in and said: Look. At some point the only actual solution is making a decision. You either accept that you can’t solve this problem, and the other person isn’t willing to – and if that is/isn’t worth leaving the relationship for. In a way, you are filibustering yourself and avoiding making a decision for yourself – and it is clearly exhausting you. Look after yourself.

    I was shocked and a bit annoyed but it’s stayed with me since. I’m prone to self neglect, as I think many women are – and that had spread into defering to my partners.

    You are capable and amazing and deserve to shape your own future.


  8. 8

    Agree with Evan on this one.   He doesn’t want to marry you, he likes things the way they are and has been ensuring, very strategically, that they stay the way he likes it.   Also agree he’s not evil or a player, he’s just following his own self interest and you are not protesting much, so he probably sees this as basically a good situation for both since you have been mostly silent and not pushed the issue very hard.   Yes, much of this is on you; men tell you pretty early on what you can expect out of the relationship; within the first year or so.   After that it’s on you if you decide to stay; you cant really blame the guy after that point.   You deserve marriage and a guy that wants to really go the distance with you.   You are still young, say goodbye and thank you and move on.   It will hurt like hell, and he might protest a bit and throw out some half hearted bait to get you to stay, but go.   It will hurt much more waiting another 5 years and the regrets of more time and youth wasted.

  9. 9

    I guess women have to wait to let the man “choose” them, but women have to start respecting themselves and their own time and lives and dump these kind of men much sooner.

    Get out. It will hurt less now than it will if you keep waiting. This man is selfish and is stringing you along because it works for him. Choose what works for you and this clearly isn’t it.


    1. 9.1
      Emily, to


      I guess women have to wait to let the man “choose” them, but women have to start respecting themselves and their own time and lives and dump these kind of men much sooner.

      I agree, otherwise waiting to be chosen and proposed to for an indefinite time is like handing over your rear end.

      1. 9.1.1

        I dated this kind of man so I know how the OP feels. And it’s a terrible place to be. But I learned my lesson,   moved on, and met someone better. I also learned boundaries with men. Some of them will say anything to get you to stay under their own conditions.

  10. 10

    My boyfriend proposed after a year together. I don’t want to get married and he knows but is hoping I will change my mind.

    I asked him why didn’t you marry your previous girlfriend?? ( 11 year living together relationship)

    He said it never felt right. She wanted to and kept asking but he did not feel it. So he used delaying tactics… when we buy a house… when we have more money… when… when….

    This is apparently a very common story.

    Do not wait if marriage is important to you.   He might be like my boyfriend. The problem is not that he does not want to marry but he Might not want to marry you 🙁   I am so sorry, must be an awful situation to be in.


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