30-Somethings Share Lessons from Past Relationships

Read these 8 lessons from past failed relationships of 30-somethings.

If you’ve had an S.O. go from Mr. or Mrs. Right to wrong and an ex-, you know the questions this raises. When you’re still riding that single train, it’s easy to feel like past relationships are a never-ending track record of failure, or simply proof of un-datableness.

Unfortunately, the world teaches us that we’re incomplete until we’ve found a spouse (as Dean Martin sang, “You’re nobody till somebody loves you”). But truly, romantic relationships never determine our lovability, just as past relationships are never really failures in the grand scheme of things. With every person who touches our lives, there’s an opportunity to learn and grow from the experience. Often, the lessons from “failed” relationships are actually the most important ones we can learn from, helping us on our journey to becoming the best version of ourselves.

I chatted with a few 30-something peers on the best lessons they learned from relationships that didn’t work out. Here’s what they said:

Don’t forget your own worth

EMILY: I found myself “rescue dating” a guy many years ago. Subconsciously, my goal was to convert him, help him stop drinking, and help him to be truly happy. Who did I think I was?! When the relationship became long-distance, I could no longer be his savior from nine hours away. I wasn’t convenient for him anymore and I wasn’t needed or wanted anymore. I realized that I didn’t think a guy would just want me for simply who I was, but rather for what I could do for him. I had a pattern of dating guys with whom I thought I had to earn my place. When I met my future husband, he didn’t need or want me to fix him. He just wanted to date me. It felt really strange and different to me at first but I knew it was helping me stop defining my worth by how much I was needed by a man.

CHRISTIAN: In my twenties, I defined my concept of love with the idea of self-sacrifice. I believed that giving all my time, life-energy, thoughts, and efforts was the true definition of love. Back then, I dated this gorgeous woman with whom I was entirely in love. I was determined to marry her, and I set out to demonstrate all my love for this person based on self-sacrifice. But I stopped caring about myself to the point that I lost my self-esteem; I couldn’t even recognize myself. To my surprise, the relationship ended because of this same reason. I learned that love is not just about self-sacrifice, but also self-love, respect, and dignity that you can bring to the relationship.

Listen to your gut

MARY: I learned to trust my gut and ask the hard questions, even if it means his answer will confirm something that’s a non-negotiable. I would shy away from directly asking, not wanting to crush my hopes with this on “paper-perfect” guy, but in the end, I had that feeling he wasn’t my forever partner. When I met my husband, I was finally confident enough and fully open to receive who he was, whether he answered my questions to confirm our fit with one another or highlight a difference. It was such a gift to know early on just how compatible we were!

BRUNO: A practical lesson I learned is to be not afraid or ashamed of speaking to others about your doubts and relationship troubles. I had a ton of very reasonable doubts, yet I never discussed them with anyone. And since I and my partner lived away from our family and friends, we never had a chance to see our own relationship in others’ perspectives. Without actively reaching out to a third person and sharing my doubts, I was left with my own, self-destructive rationalizing of every single thing that was clearly a signal not to continue the relationship. I’m not advising you tell everyone about your relationship problems — that’s not fair to your partner. But if you’re thinking about proposing and getting married, you need to air your doubts at some point, if you have any. You’re not jinxing your relationship by talking about what you think may be odd or plain wrong about it.

Your fulfillment doesn’t come from your significant other

REBECCA: I “talked” to a guy who was awesome, but just didn’t share my values. I was head over heels in love with him. I told God that my life would never be as bright if this guy wasn’t going to be in it long-term. Right in that moment, it hit me: Where should my happiness and fulfillment actually come from? I realized my life’s fulfillment came from much more meaningful sources than romantic relationships or any one human being. I’m grateful for that moment of clarity because that carried over into every other area of my life ever since.

CATHERINE: Back in the summer I dated someone who wasn’t a great texter. Whenever he’d take a lot of time to get back to me or leave me unread, my whole day would go to hell. It made me realize that I get too invested too early in relationships and depend on my S.O. to make me happy. I learned that no one has power over my happiness but me.

Don’t stay because you’re comfortable or idealizing

MIKE: I dated my first girlfriend for a year and a half. Now, usually you’d look at an extended relationship like that and assume that we lasted that long because we had a strong relationship. But the fact of the matter is we lasted that long because we were comfortable. We almost never fought, rarely challenged one another, and when I honestly look back on it, I didn’t respect her. To be clear: I didn’t DISrespect her either — we treated one another well and we had fun. But at the end of the day, we didn’t love one another enough to care to make one another better people.

MARY: I think the biggest thing I’ve learned (the hard way) is to know when to walk away. I’ve dated some great guys — but being a “great person” often isn’t enough to make a relationship work. Sometimes two great people just aren’t a great fit. The hardest thing for me is letting go of someone who is wonderful, but not the right person for me. Although I don’t regret any of those experiences, I would have saved myself a lot of time (and a lot of heartbreak) if I had walked away when I knew, deep down, that it was time. I know this sounds cliché, but I think women, especially, tend to stay longer in toxic relationships. We try to hold on and make things work when the relationship has passed its expiration date.

Don’t dwell on your exes’ flaws

BEN: After I broke up with my ex, the more I tried to analyze what had been wrong with her, the harder it was to establish a relationship with anyone new. By pondering what was “wrong” about her in retrospect, I effectively dismissed a majority of potential future relationships by thinking I may be attracted to her same faults again but in someone else. So yeah, do not over-analyze your ex’s flaws and past actions. Not good.

STEPHANIE: I feel embarrassed when I reflect on the fact that it took a lot of humility and self-examination to view my ex-boyfriends as people, and not just as experiences on the way to my marriage. When I began dating my husband, I unintentionally developed a mindset of viewing mistakes in past relationships as just “practice” for the real thing, and coming to believe my own broad narratives of my stories — narratives that largely focused on my exes’ defects — as an oversimplified version of reality. I can see now that this mindset made me dehumanize these men and, for a long time, blinded me to some of my own defects.

Pain is necessary for growth

OLIVIA: In my last relationship, there were a lot of ups and downs. I was constantly confused and never knew where the relationship stood or how he felt. In all of this stress, I started turning toward God for support, comfort, and guidance. The guy and I eventually broke up, but because I was so close to God at the time, it was the best breakup I ever experienced because I felt God with me the whole time. Staying close to God through your entire relationship can make a huge difference — no matter what the outcome — and I think that’s the goal for every relationship.

KIERNAN: I was madly in love with a guy who, quite frankly, didn’t treat me all that well and ended up breaking up with me because of my religion (which is a whole other topic). While I knew in the long-run he made the right call, it didn’t stop me from being completely and utterly devastated. I had never experienced that kind of heartbreak before and I thought I would never recover from it. I discovered, however, that seemingly unbearable pain is absolutely worth it in order to bring you one step closer toward the person you’re supposed to be with. It took a few years and a couple of other “failed” relationships, but I always tried to embrace pain as a necessity in order to prepare my heart for the person I was meant to love forever.

See the person first, not your expectations

MATT: For the longest time, I always set a standard of non-negotiables as a means to find the best partner — one with the same values, standards, and interests. One thing I’ve learned is that setting those standards too high can act as a wall; a barrier in truly getting to know someone for who they are.

You can’t force love

JUSTIN: Growing from a relationship is never easy, and I guess the first tough lesson I learned was that you can’t force attraction. I don’t mean just physical attraction. I mean you can’t force a connection, sparks, or romance. You can’t make someone want to be with you. I certainly learned this the hard way. I was hung up on why my relationship ended and wanted some sort of explanation. Every phone call, conversation, and text message from this person in our post-breakup phase gave me hope that maybe we would get back together or that I would discover the real reason that we broke up. One day, I realized sparks would fly and I would choose to love someone — I would find myself deep in conversation with someone and understand what I wanted more than anything was their happiness. No explanation needed, no trying to make someone like me. I could choose to love them every day after that, and if they chose to love me back, well, that is something worth waiting for.

Grotto quote graphic about lessons from failed relationships: "1. Don't forget your own worth; 2. listen to your gut; 3. your fulfillment doesn't come from your significant other; 4. don't stay because you're comfortable or idealizing; 5. Don't dwell on your exes' flaws; 6. pain is necessary for growth; 7. see the person first, not your expectations; 8. you can't force love."

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