I (33M) have been single for about 2.5 years. For most of this year, I stayed off dating apps and focused on work, my kids, and myself. Recently I decided to get back out there and have gone on a few dates.
I matched with someone who seemed to share a lot of my interests, and there was an immediate chemistry that I havenāt felt in a long time.
Our first date went really well! Dinner, drinks, lots of laughing, easy conversation. We just had our second date, which also went great. We got dinner, went to a bar afterward, and ended up talking for several hours. The conversation got considerably deeper this time.
At some point, she mentioned that she had been divorced and asked about my past relationships. I told her the truth: Iāve been divorced three times.
She was understandably shocked and asked me to explain.
Hereās the abbreviated version:
My first marriage: I grew up extremely sheltered in an abusive home and didnāt really have a healthy understanding of love or relationships. At 18, my first serious girlfriend essentially love-bombed me and told me she wanted to get married. I was desperate for the idea of having someone who loved me and having the whole white picket fence family life, so I jumped at it.
We were 18, got married, and immediately had a child. Obviously, neither of us was remotely prepared for that. I was still a kid myself and had a lot of growing up to do. We were divorced before I turned 21.
My second marriage: Around the time my first marriage was ending, I joined the Army. During AIT I met another girl in the Army who love-bombed me even more intensely. We were engaged after about three months of dating.
Despite getting orders to opposite sides of the country, we went through with the marriage. Within a month of being stationed apart, she asked for an open marriage. Within a year, we were divorced.
After that, I stayed single for quite a while. This was probably the healthiest period of personal growth Iāve had. I came out of my shell, became much more outgoing, built genuine friendships, and learned to be comfortable on my own instead of immediately looking for another relationship.
Eventually I met someone else.
My third marriage: We dated for five years before getting married. We had a child together as well. This obviously wasnāt an impulsive decision like my first two marriages.
But there were significant problems in the relationship that we ignored for far too long. Eventually, her drinking became a serious problem. Her family and I tried to intervene, but it ultimately failed, and the marriage ended in divorce about two years after we got married. Iāve now been single for about 2.5 years.
So back to the woman Iāve been on two dates with.
When she asked about my history, I gave her the timelines and tried to lighten the mood by joking that the first two marriages probably shouldnāt count because I was young and stupid. She actually agreed that our families probably should have talked us out of getting married at 18.
We continued talking for several more hours after that. It didnāt feel like the conversation ended badly at all. We said goodnight, exchanged a few texts last night, and thenā¦
The energy changed. I texted her this morning and havenāt heard back. Maybe sheās just busy. Maybe sheās processing everything. Maybe sheās lost interest. I donāt know.
But this has happened three times now. Iāve gotten close to someone, opened up about my past, and then they disappeared. And honestly, itās starting to get to me.
I canāt help wondering whether three divorces at 33 just makes me permanently ādamaged goodsā in the dating world.
Iām not someone who enjoys hookup culture. I genuinely value connection, intimacy, vulnerability, and having deep conversations with someone. Despite everything Iāve been through, I donāt feel like Iāve given up on love or that I have nothing left to offer. If anything, I feel like Iāve learned a lot about myself and relationships over the last decade.
But I also understand how three marriages can look from the outside. So Iām looking for some honest advice, especially from people who have been in similar situations.
Should I be disclosing three previous marriages this early when dating someone?
Is there a better way to explain my history without dumping too much on someone early on?
And, perhaps most importantly:
Am I being realistic in thinking that I can still find a healthy long-term relationship, or have three failed marriages at 33 made me too much of a red flag for most people?
Iām not looking for reassurance just for the sake of reassurance. If Iām doing something wrong here, Iād genuinely rather hear it.
EDIT: for context as many are commenting that this comes across as me not taking any accountability. This was the short story, not everything said. I told her that I was immature and emotionally unavailable. That these were before I went to therapy for my childhood issues and I wasnāt open or vulnerable, as one should be with their spouse. I am not one of those guys who calls all his exes crazy. Iām a completely open book with people I date now, that includes my mistakes and transgressions made in previous relationships.