Ask Elaine: My ex wants a second chance. How do I know if it’s worth it?

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Hi Elaine: Should I move on from my ex-fiance or try to give things a second chance? We met freshman year of college and were just friends for all four years while we each had our own lives and dated other people. My senior year he expressed that he had feelings for me and took me on an elaborate surprise romantic date to confess this. Little did I know, I actually had feelings for him too. Our love, our friendship, our romance blossomed quickly after that. He proposed four months after we started dating and I said yes.

We got along wonderfully as future spouses for about a year and, naturally, life events happened and we started to drift further apart emotionally. I started grad school and he began a new career modeling. Before we realized, our time spent focused on our individual endeavors hurt our relationship more than we knew. Over the last three years we have not once tried to set a wedding date. We went through couples counseling, endured infidelity, and ultimately I had to break up with my partner last year because it was no longer healthy or serving either of us, in my opinion.

We are very much in each other’s lives and still love each other. As much as I question if being together is the right thing for both of us, I honestly don’t think I could imagine my life without him. Now he’s asked me to reconsider our relationship, and I want to know if it’s worth trying.

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Should I: Boomeranging back to an ex-fiance when you still have doubts poses real risks. You two have a lot of history, complicated by infidelity, potentially divergent career paths, and what seems to be deep-seated doubt in your romantic compatibility long-term. That’s an uphill battle for even the most experienced life partners. But trying to transition a whirlwind college romance into a healthy adult relationship is a unique challenge because you are both still discovering and growing into yourselves.

First, you have to get really honest with yourself about why you are considering a second chance in a relationship you already concluded was unhealthy. You mentioned that the relationship was no longer serving either of you. That is solid reasoning to break up. Have any of those feelings or circumstances changed? What has shifted since you had this revelation?

It doesn’t sound like you’ve had much time apart from your ex since the breakup. Why is that? Are you clinging to the comfort of familiarity and perhaps overlooking the same set of facts that led to your initial breakup? Creating some distance from each other, even just temporarily, could be helpful to gain perspective and clarity.

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As hard as it is to navigate matters of the heart pragmatically, think of the inner conflict you’re feeling as an invitation to zoom out and think about what you (solo you) really want out of this season of your life. While you have the option to give this romance a second chance, you won’t get this time back. Your 20s offer an opportunity to lay the groundwork for the rest of your life.

What do you want to build? What or who do you want to invest your energy and time in? What are the experiences you crave? Are there career, relationship or family timelines that are important to you? What is the most authentic truth about how this relationship fits into all of that? Allow your desires, goals and priorities to guide your next step.

When you were engaged, you both prioritized “individual endeavors” to the detriment of your relationship. Maybe the truth is that right now laying the foundation for your careers is more important and urgent than laying the foundation for marriage. It’s important to honor your truth and your individual pursuits because feeling actualized only makes you a better partner. Dedicating time to deepening the relationship with ourselves will always benefit our relationships because it clarifies how partnership can be additive, or not. Compromising your own goals for someone else can have devastating effects for your relationship with yourself — and by extension, any romantic relationship.

It’s clear that this isn’t someone you’re ready to let go of. But staying in close contact could be clouding your judgment as you figure out the roles you should play in each other’s lives. What is it about the friendship dynamic that seems to work better for you than being engaged? Is there a way to foster the friendship without forcing it into a romantic context?

If you choose to explore a second chance with your ex-fiance, be honest with yourself and your partner about what your intentions are. How can you build a sustainable partnership without falling into the same ruts as before? If you aren’t ready to commit long-term, that needs to be communicated upfront. You both need to be on the same page about exactly what you’re building toward.

The pull toward partnership can be stronger than common sense at times. Ultimately, if you two are meant to be together, I don’t think a few more years becoming the best versions of yourselves will stop that from happening. Do the work, encourage him to do the same, and prepare to enter the hard conversations required of any healthy relationship with clear eyes and an open heart.

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