10 Lovesick People On The One Person They Wish They Would Have Waited For


We all have regrets. Some of us choose to accept what’s happened and move on with our lives while others can’t help but dwell on what could have been. Even if we know we can no longer be with someone I think we all have someone from our past we wonder “what if” about. I asked people across the internet who that person is for them and here’s what they told me.

1. “He begged me not to get married.”

“Nick. I’ll never forget him. He had this sandy brown hair and these deep blue eyes I could get ridiculously lost in. I met him the last semester I was in college while he was getting ready to deploy for another tour in Iraq. When we met he only had three weeks left and our attraction and chemistry was undeniable. The first night we met at a party and while everyone else was getting drunk we sat off to the side and just talked. It was like nothing else or anyone else mattered. We left the party and walked around the neighborhood, ending up at the old Elm Campus which was a popular spot to just sort of chill and relax. We stayed up until 4 a.m. telling each other everything about each other, revealing all our secrets, all our dreams. I don’t think, even to this day, I’ve ever been as honest as I was that night. So that was how we met.

We were inseparable for those 3 weeks leading up to the time he had to leave. We told each other we loved each other and made all sorts of promises to each other. I was getting ready to move to Seattle for my residency and I gave him my new address. I told him to write me. I never heard from him, though, and I was heartbroken. It took me such a long time to get over him.

Fast forward 3 years and I’m engaged. I went back to my college town to see old friends and as I’m walking down the sidewalk I see Nick. Of course, he’s just as handsome as ever. We got coffee and talked. He said he did write me but that his letters were returned. Turns out I had given him the wrong address. This was back in 2006 and I wasn’t on Facebook yet, hadn’t even joined Myspace. I just wasn’t ever a big social media person and my name is pretty common, so he couldn’t find me. That day at the coffeeshop Nick begged me not to get married. He told me he still loved me. He said he would do anything to be with me. But I couldn’t do that to Mark (my fiance). I loved him. I wanted to be his wife. I had already made that promise to Mark and everything was already planned. I just couldn’t back out for someone I’d only spent three weeks with years ago.

Mark and I are married now and we have a beautiful little girl but I still think about Nick almost every day. I think about what we would be like if we were together, how things would be different. I love Mark, I do, but it’s not the same as what I had with Nick.” – Karen, 34. 

2. No job, no girl.

“There was a girl Elizabeth I met on the subway one day on the way to an interview. We ended up getting stuck on the train and for a moment it felt like time stopped. We sat there talking for an hour until the train started going again and when I had to get off at my stop she asked me to stay and spend the day with her. We had an incredible connection and I really wanted to but I really needed to take the job interview. I didn’t get the job and some days I still wonder what would have happened if I stayed with her that day.” – Ryan, 29.

3. “I really care about him but I don’t know.”

“My situation is a little different. This isn’t someone I wish I had waited for but someone I’m wondering if I SHOULD wait for. After I graduated college I was kind of lost and unsure of my next move. I had been accepted to some grad schools and had another opportunity to travel to Europe on a fellowship and so all these things were up in the air with my life. I met Steve at that inbetween period of my life. We dated casually for a bit until I had to leave but we stayed close friends after. I always wondered what we could be between us.

I came back to our college town a few weeks ago and we reunited over drinks. Drinks turn into more drinks and we end up back at his place where we’re kissing and he’s telling me how he can’t believe I’m finally here and how he’s been waiting for this moment for so long. He says he loves me and knows that it probably doesn’t change anything but he had to tell me. Since then we’ve been seeing each other about 3-4 times a week and I think I’m really falling for him. I’m in town until Easter is over and then I’m supposed to go back to Berlin. I really care about him but I don’t know. Should I wait for him? Will he always be the person I wonder what could have been?” – Kim, 26.

4. Different cities, different jobs.

“Kelsey. We fell in love the summer after college graduation but then we both had job offers taking us to different cities. We kept in touch and visited each other a few times until she moved to my city for a project with her job. We were in the same city for a month and then I had to head to Australia for an important consulting gig. She begged me to stay with her but I didn’t. Now she’s happily married and I see the life she’s living on Facebook and I’m struck with guilt wondering if that could have been me and her.” – Brian, 33.

5. “How will I ever know if we could have made it work?”

“I dated a guy on and off for a couple years and although we were close friends and spent a lot of time together, nothing ever became a serious relationship. When I announced I was moving across the country he told me that he had feelings for me and that he thinks we’re good together. I’m sitting here, now, in my apartment in San Antonio with these boxes all around and I’m wondering if I should just go back home to him. How will I ever know if we could have made it work?” – Brianne, 25.

6. Life is too short to wait for someone.

“There was a time I used to long for the past. For past loves, past relationships, even if I was the one who ended them. There was in particular that used to haunt me. I broke up with him even though nothing was really wrong. I graduated college and we had been together 6 years. I felt like I needed time to be single, to be on my own finally. Then after a year or so alone I thought I wanted him back. For a long time I felt guilty and sad about not waiting for him to finish school and for not waiting for him to grow up and make the same decisions as me. But eventually I grew out of that. There’s no sense in longing for the past or waiting for anyone. You can only live in the present moment and move on with your life. Life is too short to wait for someone it didn’t work out with the first time around.” – Lisa, 34.

7. She always had a boyfriend.

“I wish I would have waited for Megan. She was the kind of girl who always had a boyfriend, always had someone on her arm. Her and I would flirt a lot when we both worked at the radio station together and I grew quite fond of her. I always had this idea that if she would finally leave whatever loser she was dating and take a chance with me we could have had a good life together. Who knows.” – Paul, 24.

8. “I wish I would have believed in him more.”

“I watch way too many movies and I have an idealized version of love and dating and ‘happily ever after.’ I wished I would have waited for my last boyfriend. He was an addict and he used money I had saved up in my sock drawer to buy more coke. I broke up with him and told him I couldn’t deal with it anymore. A year has passed and now he’s moved on, successful, no longer an addict. I guess I wish I would have believed in him more and believed he could do better. I wish I would have waited for him to get stronger.” – Kim, 26.

9. “I don’t want to wonder 5 years from now if breaking up with him was the biggest mistake of my life.”

“I would have said my ex but right now I’ve just decided I’m going to give my ex-boyfriend another chance. We have this incredible connection I just haven’t been able to find with anyone else since we broke up. It’s been 7 months since the break up, which I think is plenty of time for us to figure out what we want and if we both want each other. He’s been sending me love letters and telling me how he feels. I don’t want to wonder 5 years from now if breaking up with him was the biggest mistake of my life. I want to give this 2nd chance a real shot. If it doesn’t work out this time around then I’ll know it wasn’t right.” – Kelly, 22.

10. Should have said yes.

“Oh, my ex-wife. I miss her a lot. We were married for 10 years. We were very young when we married and so we both made a lot of mistakes. No one tells you how to be married or how to be a good husband and so I was young and dumb and probably treated her worse than she deserved. Before we signed the divorce papers she asked me if I wanted to wait on it but I said no, let’s just do the damn thing. Looking back I wish I would have said yes.” – Carl, 44. Thought Catalog Logo Mark

Former senior staff writer and producer at Thought Catalog.

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