How To Know Whether Dumping Your Boyfriend Was A Mistake

Breaking up is messy business, whether you initiate the split or are dumped against your wishes. No matter the circumstances — his cheating or yours, falling out of love, discord of personalities, or just naturally growing apart — it's tough to move on. When you end a relationship, you can be plagued by pangs of guilt or feelings of regret that leave you second-guessing your decision. Sometimes those feelings are part of the natural cycle of mourning the loss of love and of letting go. But at other times, those emotions might have you rethinking your choice and leave you wishing you hadn't ended it.

I polled nine women — some friends, some random — about the feelings of regret they experienced after they ended a relationship. I even revealed my own experience of regret in love. Then, Dr. Jack Burke, a relationship therapist based in Maine and who appears regularly on NBC's WCSH, analyzed whether or not these feelings were signs of a mistake, indicative of something else, or simply a normal part of the process. Dr. Burke offered up this valuable nugget of wisdom on relationship regrets in general: "If you start a romance with hope, of course there is regret. The emotion is healthy and normal."

Names and certain details have been slightly altered for privacy purposes.

Let's begin with me — since I asked people to get personal, it's only right that I put it all out there, too. I ended a year-long relationship — one that was particularly brutal since the guy was in a band and often on the road. He was also totally unfaithful — something that his bandmates revealed to me. Despite how furious I was about his extracurricular activities, I remained jealous at the idea of him finding someone else, moving on, and being happier with someone other than me. Those thoughts told me that I wasn't really fully down with ending it.

Dr. Burke noted that my post-breakup jealousy was proof that "we always have regrets, since once the pain stops, we remember why we liked and cared about the person." It wasn't necessarily an alert from the universe, telling me that I needed to reconsider my actions. But in another set of circumstances, like if I had broken up with a boyfriend who practiced fidelity, my feelings of jealousy may very well have been a sign that I made an error when dumping my dude.

Iris broke up with her boyfriend because things became so... familiar. "I felt like it was time for a change, to shake up my routine," she said. "But when I was doing all the things he and I used to love to do together, but without him, I second-guessed myself so hard. We actually got back together for six months."

Dr. Burke pointed out that ending a relationship with someone who is similar to you can ultimately make you feel like you are "breaking up with a best friend." Dating someone just like you can be a safe proposition, which could lead to feelings of second-guessing your decision to end it. Whether or not you value safeness and similarity in a relationship is a matter of preference. In this case, they did reunite. Therefore it'd seem that having trouble doing activities a la carte when you previously enjoyed doing with your significant other is a sign of the breakup being a potential misstep.

Carrie briefly dated a high school friend after reconnecting with him during a college break. She explained, "He had this geek appeal that I love and we engaged in mild flirtation. As the holidays got into full swing, we were at the same gatherings and bars. So we hooked up. It was nothing serious, since we were both heading back to college. He asked if we would see each other on a more regular basis, since our colleges were only 90 minutes apart. I politely declined, saying I would be busy with internships and paper-writing, when in fact I had a couple of love interests back on campus I wanted to dabble with." However, when summer arrived, Carrie ran into Adam again while back home. She explained, "He still had the geek appeal, but had progressed to a whole new level. I was kicking myself. I should never have blown him off."

Dr. Burke brilliantly compared Carrie's pangs of regret up to the same psychology explored in those new Taco Bell "Order Envy" commercials — you want what you can't have. And when something is outta sight, it's also outta mind, too. "It's natural have second thoughts when you make one choice over another," he said.

Jenna dated an Air Force pilot she was partnered up with in a wedding. "We kept in touch and he sent me a plane ticket to come visit him for his birthday," she recalled. "It was magical in every way. I was being courted, by a gentleman, which, after years of dating broke, dirtbag musicians, was an incredible feeling." The literal and figurative distance became a problem. "He was looking for a conservative Christian wife with whom to breed children to be Christian missionaries, and I was looking for a good time and maybe a boyfriend. It likely wasn't going to be a match made in heaven," she remembered. "I adored him, but I wasn't ready to give him what he wanted, so I'm guessing he began looking elsewhere. The last straw came when I didn't hear from him at all for two entire weeks after he flew out of the country for a mission. I deleted his number, and he popped up again, asking what was wrong, saying his family was visiting and he was just so busy that he couldn't even shoot me a message to let me know he was alive."

She continued, "I tried to believe him and trust him again, but it just was irretrievably broken. To this day, I wonder what my life would be like if I had stuck it out. Would we be married? Would we have kids? It took me longer to get over that heartbreak than any other, because I kept telling myself if I were just a little more patient, a little more understanding, or a little less needy, I could've had the man of my dreams. It worked out for the best, but I'm still human, and sometimes still miss him, even though it would never have worked out."

Dr. Burke commented that Jenna's emotion cycle was incredibly healthy and she truly examined her motives and feelings. Since she has moved on, the looking back is normal but not an indicator of a mistake and here's why. "When you think, 'I could have made it work,' it's because you are remembering the more positive aspects." Indeed, hindsight is 20/20.

Kelli revealed that she once "broke up with a guy because he vented about a fight we had to one of my friends, who he had only just met. He was very unapologetic about airing my dirty laundry to her and didn't quite understand why I was upset. When the dust settled, I thought I was being irrational. He had always been nice and I realized he wasn't being malicious by telling her about our fight; he needed to vent. I really felt I made a big mistake by abandoning someone who I believed to genuinely cared about me over something so silly."

They briefly reunited. But she eventually learned they were not compatible, saying, "It turns out my initial reaction and instincts to leave were correct."

Dr. Burke noted that most of this scenario is common and perhaps things could have further improved during the reunion if the couple had a frank discussion about privacy versus secrecy and about setting boundaries and sticking to them. In this case, the ultimate end result, which was the second breakup, was inevitable. It's clear that other problems asserted themselves and caused the permanent split.

Lola revealed that she struggled with the end of a serious relationship by looking inward. She admitted, "I regretted that it failed, but I did not feel like it was a mistake, since I put everything into it or that I left no stone unturned." While it's true that one can always look back and feel that they should have done more, that can also be a sign of perfectionism.

Dr. Burke encouraged anyone enduring this emotion in the middle of a breakup to think long and hard about whether or not they feel the split was a mistake because of the person or because they ultimately had to let go and give up on the relationship. Clearly, it can go either way in any pairing. But if one is a perfectionist, she might continue to blame herself and consider not being able to fix it the biggest mistake.

Sonya shared that when she was young and dating her first boyfriend, another guy came onto the picture. "My ego thought I could do one better or maybe I thought could have two boyfriends and play the field a bit," she recalled. "What a jerk I was. So, I broke up with my boyfriend and the person I broke up with him for eventually left me for someone else. I questioned if I shouldn't have indulged my ego."

While making mistakes in life is an ageless experience, Dr. Burke stated that this is the painful and normal reality of learning the ropes of love and of growing up. Thinking there is always something better or tastier on the menu and wishing you were having what the person sitting next to you is having can be a mistake, since it distracts you from appreciating what's right in front of you.

Marnie shared that she and her significant other broke up for reasons she can't even remember. What she does remember is that it wasn't a clean break. "I kept going back to him to hook up and have sex, which felt like a sign that breaking up was a mistake," she mused. "If it was the right thing to do, why couldn't I fully walk away? Trust me — it wasn't just about good sex, either. It was about him. It was him and his personality that kept pulling me back."

Dr. Burke's assessment in this case is that if you keep going back, there might be more to it. "That draw was still there and it could be out of utility," he explained. "But there is something still there. If the person was sitting across me in my office, I'd ask is about the situation or the other party. I'd ask, 'What are you holding back?'" It's pretty obvious, though. If you keep returning to the well, it's because you are getting a need met or a satisfaction from doing so. That's also a pretty definitive sign that the spark remains and maybe the break needs to be reconsidered.

Maria confessed that this is how she knew that she made a massive mistake when she broke up with her long-term boyfriend, but she couldn't break up with his family. "I couldn't stop texting his mother, meeting up with her for lunch, and going shopping with his sister. I was so close with this family and I continued to stay in touch with them. He and I eventually got back together and got married." That might not be a common scenario, but it's also indicative of the importance of familial bonds as they extend to and support romantic relationships.

When you also fall in love with the other party's family, those attachments are strong, Dr. Burke explained, further noting that as long as the two parties in the romance actually still love each other, all the while loving their family members, then it was a good decision to get back together. If you can't let go of his family, then it was likely a mistake letting go of him.

After Liv split up with her boyfriend, she struggled to do things she liked, because they reminded her of her former love far too much. She reminisced, "I couldn't do any of the stuff we used to do, like go to football games or [watch] scary movies. I struggled to do the things we used to do together. It reminded me too much of him, even though I enjoyed doing all that stuff before we start dating and doing it together."

This is a complex experience, since missing your partner this much could be indicative of your split not being the right thing to do. Dr. Burke explained that this can also be a pain avoidance reaction and that the sentimentality towards the past might not have as much to do with the ex as it does with memories invoking emotion.

After speaking with Dr. Burke, here are my main take-aways about thinking of feeling that ending a relationship was a mistake: There are always going to be plenty of things that make you feel like you did the wrong thing, but they are part of the normal grief cycle. But there are also situations that spring up to tell you, "Hey! You may want to rethink this." You just need to follow your heart, look deep into yourself and figure out what you need. Believe your gut when assessing whether or not a relationship is truly right for you.