Tips and Tricks

Take Two: How to Propose to Someone Who’s Been Married Before | Rare Carat

Dating someone who's been married before is no biggie. But deep down, you want your marriage proposal to be jaw-droppingly better than anything she's ever seen before. That's where things can get a little tricky.

Despite the fact that researchers report that nearly half of US adults are divorced, many formerly married people still have mixed feelings about that part of their past. The last thing you want to do is hit the wrong note in your proposal and end up triggering some unwanted emotions. (Or worse, a negative response!) Yes, you want your marriage proposal to be the best one yet, but here are some important tips to consider before asking her to tie the knot (twice).

Engage in some real talk about what you both want

While the "total surprise" proposal is the perfect play for a certain kind of bride-to-be, when you're dating someone who's been down this road before, it's important you DO NOT jump the gun.

But you know that already, right? Today, 94% of couples discuss marriage before getting engaged. And with divorce rates being what they are, that's probably a good thing. Assuming you and your partner have already discussed marriage and decided that it is 100% something you both want, the next step is to go ahead and talk about what she wants in a proposal.

Your partner may or may not want to share the specifics of the last proposal with you. That's ok. Just ask if there's anything she definitely doesn't want. For example, some previously married people would loathe the idea of a public proposal, while others might actually want this proposal to be bigger and louder than the last.

And we don't have to remind you, you better ask about what she wants in an engagement ring, but don't but pressure on yourself to make the ring bigger, and better just because you're insecure. Get her what she wants, to the best of your ability, but don't go into gobs of debt trying to outdo the other guy. She's marrying YOU for a reason.

Getting engaged the second time around, all comes down to each person's past experiences and by now, you probably have a pretty good idea (or at least, a rough idea) about what was or wasn't working in her last relationship. Skip the second proposal faux-pas and always take time to consider her past, and NEVER rush into a proposal just because it sounded great in your head or in that one Julia Roberts movie you saw.

Make your proposal way more awesome than the last one

One foolproof way to win with someone who's been married before is to use those super special details from your relationship to guide the proposal.
For example, proposing at the location of your first date together is a surefire way to make it special. After all, that's where you guys kicked off your unique romantic adventure. Who could really compete with that? Plus, there's almost no chance that location would have had any significance in your partner's last relationship. (We hope.)

Or, let's say you have a specific hobby or interest that really bonds you together. Go ahead and work that in. Maybe your partner could never go skiing with the ex, but the two of you love your weekend getaways in the slopes. Plan your proposal for your next ski trip and you'll automatically blow that last proposal out of the water. (And of course, it doesn't hurt to get the ring right.)

But remember, your proposal doesn't have to happen among the majestic Alps. Different relationships have different expectations.  It can be as simple as sitting in your living room watching the same movie you saw together on your first date. In many ways a second (or even third or fourth!) chance is so much sweeter than anything that came before. What matters is that THIS proposal is yours and yours alone.

And when you're ready to finally go ring shopping, know that we totally have your back for the best ring. No matter how many times she's been married before.

Jenny Beres
Jenny Beres
Jenny is an experienced copywriter and recovering diamond-aholic. She’s been writing for Rare Carat since 2016.