😲I've been 'almost' engaged 3x
1-800-Bridesmaid
📞 Hello? Hi. It’s me, Jen Glantz. Welcome to the 1-800-Bridesmaid, by Bridesmaid for Hire. A place where real stories are shared and your best advice is given.
This week: The caller admits she’s almost been engaged 3x but hasn’t had any luck meeting someone she wants to spend time with. She wonders why and is desperate for advice.
Last week: A bridesmaid feels like the friendship is broken in a million pieces. Can she end it before the wedding? Here’s what you told her.
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Dear 1-8-00-Bridesmaid,
I'm Maddy from Boston. I just turned 37.
My friends call me the "Almost Fiancée." Over six years, I've had three serious relationships following the same pattern: we dated for about 18 months, discussed marriage extensively, looked at rings, and planned our future. My recent ex, Jake, even had me try on his grandmother's ring that had been sized for me.
But two weeks later, at what I thought was our engagement dinner, he said he "couldn't see a future with me." A year later, he proposed to his coworker.
The worst part? I knew these men weren't right for me. I ignored red flags each time—a drinking problem, controlling behavior, disagreements about wanting children.
At 37, I feel the pressure. My doctor used "geriatric pregnancy" at my last checkup. My sister just had her third child. My parents send egg freezing clinic links.
I'm terrified I've wasted my prime years. I find myself thinking "maybe I should have just compromised more" and calculating on first dates if we could get engaged within six months.
How do I break this cycle without feeling like time is running out? Am I chasing marriage more than the right partner?
-Maddy
Wondering what an expert has to say?
Ilana Dunn, dating expert and host of Seeing Other People is a guest on 1-800-Bridesmaid this week. She heard Maddy’s question and here’s what she had to say:
Have advice? Share it below. Maddy is looking at everything you share!
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Sounds like they all did you a favor not going ahead with it - since you weren't fully sold on them anyways.
1. Get pen and paper and write down your non-negotiables. Looks like: you want marriage, you don't want someone with drinking problem, who's controlling, or doesn't wan't kids, etc. You need to be clear about your absolute non-negotiables.
2. Be ready to bring up these conversations on the very first date/meeting. Don't wait till they sweet talk you or you fall in love, and then you start checking for these after the fact.
On each date, be warm, calm, but deliberate about filtering out for your non-negotiables. Of course, you have to be willing to be alone if you can't find someone who'll meet all of your non-negotiables. So, practically, it's a good idea to have a few core of those, and not have like 15 non-negotiables, for example.
3. Put yourself in environments where you can meet lots of men you'll want to marry. Dating apps, IRL, etc. Then, go through Nos. 1 and 2 for each one.
I'll be honest with you though: this will be easier if you were younger and didn't have these pressures (external or otherwise) due to your age. Just a heads up
Don't ever ignore the red flags! You need to love yourself more. It's not a bad idea to freeze your eggs. Although I think building your self-confidence is now a priority. You'll see you're going to attract different men. And don't dwell on the past and be sad about the years you've lost. Time to open your new chapter in life. It's called I love myself first. And that's in no way selfish. Good luck with your new episode in life.