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.