Can I Ask My Boyfriend for a Timeline to Get Engaged?


I stumbled onto your blog a few years ago, after getting nowhere in my dating life, staring down the barrel at 30, and starting to get terrified that I was going to spend the rest of my life alone. I read almost all of your posts and one of your books, and while I admit I initially had trouble with some of your advice, it did make a certain amount of success if I was honest with myself. And definition of insanity, right? Doing the same thing over and over and expecting different results? Clearly what I was doing wasn’t working. So, I gave your advice a try, and I’ve now been with a wonderful guy for 2.5 years, we’ve been living together for a year, and we talk about marriage and kids as something that will definitely happen eventually. So, I want to start with a heartfelt thank you, because before I found your site, I’d given up hope of ever getting here.

There is, of course, a “but”…

As I said, we talk about marriage and kids as an eventuality, but there’s never been a specific timeline attached to that. We’re both recently 33 now, and for the past six months, it feels like all anyone ever wants to talk to me about is why we’re not yet engaged, when we’re getting engaged, my advancing age, my declining ovarian reserve, etc. It sucks. It’s like we hit the two-year mark and I magically stopped being a person and turned into a naked left ring finger and some ovaries — all attached to a ticking time bomb.

But if it was just the rest of the world, I could handle it. Once we hit the holiday season, several of our friends who have been dating for a shorter time than we have got engaged. My reaction has shocked me. The initial announcements, proposal stories, engagement photos, dress photos, etc. have all been like punches to the gut. It has hurt. A lot.

Emotionally, I don’t think I can take another “engagement season” if I’m not part of it.

Finally, my question: What are your thoughts on asking your partner for an engagement timeline? I’ve read your recommendation that couples not get married before three years — but I couldn’t tell if that meant waiting that long to get engaged, or just not walking down the aisle until the three-year mark. I’ve also read your advice that women just be clear about what would make them happy, because a man who loves you will want to make you happy.

So… do I just make some general statements about how I’d like to get engaged sooner rather than later? Do I set a date in the future and ask now for a ring no later than that point (seems ultimatum-y and unromantic)? Do I hold off altogether until we hit the three-year mark in the hopes that he pops the question on his own by that point? If he doesn’t, we’ll only be a few months away from engagement season, and since I know a ring is not an insignificant purchase, I don’t really want to spring an “oh hey, I’d like to be engaged in the next 60 days” on him at that point.

The added wrinkle for us is that he is miserable at work. He constantly talks about all the things we’ll do once he has a new job. It has a very “that’s when our lives will really start” feel to it. I’m worried “get engaged” is on that list. And he’s been “going to get serious about finding a new job in the next three months” the entire time I’ve known him. If I can ask for a timeline, can I ask for an unconditional one?

Thanks, Evan!

– Liza

Thanks for the kind words and the long email, Liza.

Let me begin with a theory of mine: you should never be afraid to ask your boyfriend a question, because asking the question doesn’t change his mind. All your question does is reveal what he’s ALREADY thinking.

You should never be afraid to ask your boyfriend a question, because asking the question doesn’t change his mind.

Once you understand that, you can feel comfortable to express yourself freely, without fear. Because you’re not issuing an ultimatum. You’re asking a question that deserves an honest answer, and a good man (which I presume you have) will answer you honestly.

Is there more “power” in being the cool girl, letting things play out organically, and giving him the space to choose to propose to you when he’s ready? Absolutely. But I don’t think this is a case of either/or, where you either have to remain silent with anxiety or you give him 60 days to pull the trigger.

A good rule of thumb in life is, “First seek to understand.” So instead of hitting him over the head with a spreadsheet of your ovulation cycles, how about, in a tender moment, asking him how he’s feeling at work and what he’s doing to switch careers. Your interest in HIS happiness should be at least as important as his interest in YOUR happiness.

Once you’ve allowed him to speak, listened to his plan, and validated his feelings, you can then pivot to the crux of your issue. It is certainly NOT about your friends getting engaged faster nor is it about “engagement season,” which in guy-land isn’t even a thing.

Most importantly, remember this precept:

Communication isn’t about finger-pointing. It’s about problem solving.

  • His problem is that he doesn’t feel happy or stable to make the most important decision of his life (which is perfectly valid.)
  • Your problem is that you’re anxious about getting married because of your friends moving faster and asking uncomfortable questions.

I understand your feelings, but honestly, in my opinion, your fears don’t outweigh your boyfriend’s fears. You can get married at 35 and still have 2 kids. Your boyfriend can’t do much at all until he’s no longer miserable.

Your boyfriend can’t do much at all until he’s no longer miserable.

Which is why I would approach this in such a way that emphasizes understanding for his plight and minimizes your plight (“Jessica couldn’t believe you didn’t propose, much less during last engagement season!” is unlikely to get you the reaction you want).

Once you hear how he’s feeling, you can talk about your desire to see a general pathway to marriage — without pressure or ultimatums — just so you can breathe easy and know you’re on the same page.

He will be able to respect and understand that, and, if he’s committed to you, will do everything he can to deliver. I can assure you that your “timeline” will be dependent on him getting happy, not on 60 days or 3 years or the peer pressure and optics from your friends.

If you love him and trust him, you must give him the freedom and support to get there, instead of ratcheting up the pressure to make a permanent choice before he’s ready.

If you love him and trust him, you must give him the freedom and support to get there, instead of ratcheting up the pressure to make a permanent choice before he’s ready.

I know that may sound like a very man-friendly answer, but then again, you wanted to know what he’s thinking and what will get you the best results. This will.

Good luck, my friend.

Join our conversation (97 Comments).
Click Here To Leave Your Comment Below.


  1. 21

    Mrs Happy

    I wonder if I could pick your brains to understand your perception a bit better?

    Reason being is that my most recent ex put a lot of the behaviours I didn’t like/understand (which I at times found frustratingly selfish/thoughtless) down to us not being in love. I agree with us not being in love, we didn’t get to that point before things broke down,…but for me there’s no discernible difference between how I treat a person who I like/am attracted to/exclusive with/want to build a relationship with but am not yet in love v’s all of that and also in love. Yes, it’s stronger, but it’s not a huge difference. For me.

    I guess my point is this: if boyfriends are ‘disposable’ and husbands aren’t, how does a boyfriend get to the stage of becoming a husband? It’s not like you treat them as ‘meh’ until you walk down the aisle, as otherwise you’d never get to the point of walking down the aisle! Or do you mean you treated them as disposable until you got to a place yourself where you were serious about getting married and then your behaviour towards boyfriends (who had husband potential) changed?

    I don’t really understand how a person can spend pretty much every weekend with someone, clearly enjoy their company, ask them to stay a day longer and work from home often, sleep with them, introduce them to their friends, drop things like “my parents say hello” into the conversation, and still be like…well we’re not in love and you’re not my I’m still keeping this emotional distance between us… Not something I can get my head around (but assume you can).

    In this instance it doesn’t really matter as it’s in the past, but I would love to better understand this from a woman who kinda thinks like a man! To help me in future.

    Thanks 🙂

    1. 21.1

      I’m also curious as to Mrs Happy’s response, Marika.   But I will say that I am a man and I think the same way as you.   Never saw girlfriends as disposable.   Saw each one as special, each relationship as precious.   But that might be because I was searching for marriage and a long-term relationship rather than experiences.   I was not in love with falling in love.   I simply wanted to fall in love once.   I think that the attitude of the individual might be the key.   I just wouldn’t want you to think that Mrs Happy’s approach is typical of all males, though I do think it is more typical of males who are avoidant.

    2. 21.2
      Mrs Happy

      Dear Marika,

      this will be a quick answer because I’ve just finished cycling all afternoon, and am slimy and grimy with sunscreen and city traffic dirt (yukko), and yearning for a shower.

      I wonder if I’ll come to regret the word disposable.   It may have been incorrectly used.   I don’t think of any human as disposable – quite the opposite.   What I meant was, I could almost always (with maybe 2 exceptions) move on between boyfriends without much upset, no gnashing of teeth, no Heathcliff-and-Cathy style fracturing of the soul.   Some – most, as naturally I have impeccable taste! – were great guys.   I have a few ex’s I’ve kept as very close friends and they are wonderful people.   But once we had broken up, whoever did the breaking, that was sort of it for the romance connection part, and my emotional self moved on.

      Compared with my first marriage ending, a boyfriend break-up was tiny, only ruffled the surface of my life for a very short while.   A marriage ending removed my hope for my entire future as I saw it and was cataclysmic in a way a boyfriend break-up never was. Probably a better word than disposable would’ve been replaceable, but even that doesn’t capture what I meant.   I basically meant, any relationship with a boyfriend, was far less an integral part of me, than any relationship with a husband.   A bit like Dido’s ‘Life for rent’ song lyrics maybe: I had to stop superficially renting and become more invested.

      And boyfriends only got to the stage of being husbands when I changed my attitude towards marriage.   It actually had nothing to do with the guy, or how I treated the guy or vice versa.   I was really good to boyfriends.   I didn’t hold back from giving to them.   But there was/is a host of stuff I wouldn’t do for a boyfriend that I would do for a husband, e.g., donate an organ, combine assets and share bank accounts, buy property together, live together, move, share my life fully, have children, support his career even at a cost to my own, financially support, spend my precious time and energy giving to his family and friends, etc.   I’ll give more, within a marriage.   I treated boyfriends well but they didn’t get the whole package.

      Don’t most people do this???   If I’m truly unusual in this I’ll own it, I am a bit weird really, but surely the desire to not be ‘all in’ is what keeps people from marrying.

      If your guy excused his selfish behaviour with “we’re not in love”, I suspect that was just an excuse to keep doing whatever he wanted to without considering you as much as a boyfriend should.   People don’t change their character when they fall in love, they’re just nicer for a while.

      1. 21.2.1

        Don’t most people do this???”   LOL.   Mrs Happy, when I first came to this site years ago, I was amazed at the way women described men, at the problems they were having.   Because I was nothing like the men they were describing.   So I assumed these women were misinterpreting their experiences.   It took me an embarrassingly long time to understand that I didn’t relate to these men because in some ways I am an exception to the general rule.   As are you, by the sound of it.

        An anxious person treats all relationships as special because they yearn to connect – spouse or not.   They are all-in very early.   An avoidant person holds people at a distance so as not to invest too much or be too affected – they are really never all-in.   Rare is the avoidant person whose mind is logical and forward-thinking enough to consciously make a decision to overcome their own avoidancy in search of logical goals for future happiness.   To bind themselves like Odysseus with the sirens to prevent themselves from going where they shouldn’t.   And even if those goals are ultimately driven by eons-old algorithms (“the time has come to reproduce – find good genes and support!”), most don’t do it in an intelligent way.   Sounds to me like you are the exception, which I think you ultimately know.

        1. Mrs Happy

          Dear Jeremy,

          if we’re pigeonholing, maybe I’m a secure type, with very high standards and a love of her own company.   Or witchily good at manipulating the world around her.

        2. Jeremy

          Anything’s possible.   I once saw a pigeon swimming in a pond.   It had a bill, and quacked, and water rolled off its back.   Damned strangest pigeon I’ve ever seen.

        3. Jeremy

          Ugh.   I apologize.   My answer to you was too glib.   I obviously don’t know you, and I’ve made assumptions that might be totally wrong. I apologize for offending.

          Anxious and avoidant – these aren’t terms designed to pigeon-hole.   They are a spectrum with a broad middle-zone, like the introvert-extrovert spectrum.   Do you think you fall in the middle?   Do you think that where you have fallen in your past has varied?

        4. Mrs Happy

          Dear Jeremy,

          glib doesn’t bother me at all, I just went to bed because it was 11pm -we’re on opposite sides of the world as you will recall.   Went and read about bear attacks in Bill Bryson’s ‘A walk in the woods’ and then in a Kelley Armstrong novel too (what are the chances, no wonder I’ve bears on the brain), before sleeping actually; only Bill can make such a subject funny.

          Maybe I am odd.   I assimilate easily so I don’t look or behave oddly but God knows there are so few people around me whom I truly connect with and who stimulate my mind, that I am on a blog communicating with individuals from the northern hemisphere (plus Marika who is probably within 10km of me and enjoying this lovely autumn morning too).

          I’m suspect I’m too close to the action to type my attachment style correctly. But one of the main aims of my mothering so comprehensively (and exhaustively) and sacrificing so much for them is that I believe to instill in my children a secure sense of self, and a secure attachment style, is one of the best things I can do for them.

          The assumptions you’ve made have occurred based on the information I’ve provided, all of which is correct and carefully given, so your assumptions are likely reasonably on point.   You have sought to understand the mind over the last decade or more and your wife is a psychologist so I comfortably accept your tendency to categorise and box at times. You will not offend me. You aren’t stupid, nasty, reductionistic, insulting or argumentative and you don’t leap to illogical conclusions. Setting aside distance, the only bad thing so far is the lack of bear stories.

        5. Jeremy

          Mrs Happy, thanks for your gracious reply.   I was bothered all day by the possibility that I might have given offense, when what I’ve tried to do is the opposite.   As to your comment here,

          I assimilate easily so I don’t look or behave oddly but God knows there are so few people around me whom I truly connect with and who stimulate my mind”   Me too.


          But one of the main aims of my mothering so comprehensively (and exhaustively) and sacrificing so much for them is that I believe to instill in my children a secure sense of self, and a secure attachment style, is one of the best things I can do for them.”   Me too.   This is especially important to me knowing what a number my own parents did on me, unknowingly.   Though I sometimes wonder what advantages my own kids will lack because I’m trying so hard to raise them secure.   My own sense of self-sacrifice, the insights I’ve gained through hardship and personal growth – were they worth the cost?   Will my kids lack those things?   Will they one day lament their parents’ lack of good judgment as I do?   Time will tell.   We can only do the best we know how.


          Setting aside distance, the only bad thing so far is the lack of bear stories.”   My only run-in with a bear was vacationing in Tofino, on the west coast of Vancouver Island.   We were leaving early to go sea kayaking and a black bear was rattling around the garbage can of the B&B we were staying in.   Wasn’t interested in us, though, so no good escape story 🙂

        6. Mrs Happy

          Dear Jeremy,

          I worry similarly too – my daughter has few life aims and little grit and I worry her ride in life has been too easy, which is my fault really.   She’s still very young though so hopefully her drive and determination will improve.

    3. 21.3


      Your ex’s “we’re not in love” excuse for his behaviours made me smile because I had an ex who behaved really rather badly towards me bring out the same excuse once. He phrased it a bit differently: he told me I didn’t give him that “in love” feeling which some girls do, and went on to cite an ex of his who  did  give him that “in love” feeling. This was after ignoring me, sidelining me and pretty much treating me with disrespect, and this was the reason he offered. We broke up at that point. He wasn’t a very nice person.

      I think there is a huge difference between not being all gaga and wrapped up in someone, like you are when you are in love, and not treating someone with affection and respect. The two are not the same at all. The latter is the very least you’d expect from someone you were dating, even if you were not in love yet. If he was pointing the finger at you not being “in love” for behaviour that was selfish and thoughtless, chances are he simply doesn’t want to own it/change/apologise.

      As far as how someone gets from being a boyfriend to a husband, I agree with Mrs. Happy’s comment entirely. I can usually move on from a boyfriend in anything from a few weeks to a month, but it took my almost three years to get over the end of my marriage. The commitment was just so much deeper. I would also add that boyfriends can be in your life anywhere from a few weeks to years. With a husband, the bond that you have solidified with marriage has usually built up over many years and many shared experiences, and is much stronger and more difficult to break.

      1. 21.3.1
        Mrs Happy

        Dear Clare,

        thank you for this – I was beginning to feel I had green skin and everyone else was a different species.

        1. Marika

          Oh Mrs Happy, not at all!

          I think, in fact, you have the best approach. You’re prioritizing your needs and feelings, and not getting too swept up until it’s real. I wanted to understand better how to do that. I can only do that if I’m not that into them. And obviously I don’t want to confine myself to people I don’t care much about!

          I’ve been married and while, yes, that break up was by far the worst, the feelings from each breakup have been similar. It’s just that marriage break up took way longer to heal from.

          Trust me, I would love to be part of the green skin genus! 😀 I just have all these “but why did they do x or say y”..lingering questions for weeks, rather than “meh, not right for me”. In a way, with my husband it was easier, as I knew him well enough to know exactly why he did what he did.

      2. 21.3.2
        Emily, the original


        I can usually move on from a boyfriend in anything from a few weeks to a month,

        You’re big into screening. How do you screen for this? If I’m spending a significant amount of non-sexual time with someone — as Marika wrote: incorporating that person into my life, spending most weekends together, introducing family and friends, talking on the phone every day — I’m in and I’m thinking long-term. If I’m thinking short term, I don’t spend a ton of time with him and what time is spent is largely entertainment (sex). The last guy I was dating casually wanted to help me move. I said no because I knew I didn’t want him to become a part of my life. I compartmentalized him.

  2. 22
    Alicia Wood

    I told my husband, “I will no longer be using birth control. You can decide according whether you’ll be having relations with me or not.” (We had 2 at the time.) 5 children (from 10 pregnancies) later I realize I vehemently decry birth control & believe it has led to (along with the downfall of the family & society) painful discussions & situations like this one. Without birth control this question would not even be an issue. Sex = babies, therefore equals marriage or single parenthood.

    I always intended a large family (& breastfeeding). If I couldn’t have found a man to play I’d have been a welfare mom.

  3. 23

    I disagree. You claim you can have 2 kids after 35. Maybe her but not all of us. My son is already 15! In 3 years he will be an adult. Why would I want more kids after that? To just say nonchalantly that you can have 2 kids after 35 is absurd. I already have fertility issues at 32. Please stop spreading that misinformation. Fertility   is pretty lower at 35..

Leave a Reply

Your email address will not be published. Required fields are marked *