There’s a lot of advice for healing and finding love after a divorce. There’s not much advice for single women considering whether or not to date someone who has been previously married. Dating a partner who has already planned a wedding, had a marriage, and built a life with someone else is tricky. 

For some, the idea of dating a divorcee, might be an automatic no. For others, it might not be a big deal. Some might see it as an asset. It might be a possibility to date a partner with more experience and who has learned from a failed marriage. 

While everyone’s experience is different, I wanted to share my experience dating someone who’s been previously married. 

The Beginning of Something New

Dating a divorcee might seem uncommon. When I began dating my boyfriend, I quickly found this not to be the case. If you are in your late 20s or older, dating a divorcee is not unusual. There is a community of people dating or married to someone who was previously married.

When I began dating my boyfriend, I had an open mind about this topic. I know that the older the men you date, the more life they have lived. They have also walked through more adult situations. After all, the average age for couples going through their first divorce is 30 years old.

Again, every dating situation is different. My boyfriend did not have kids from his previous marriage. I would have still been open to date him if he had kids, but I would have had hard-hitting questions. I also would have wanted to understand his relationship with the kid’s mother and the dynamics with his kids. 

When to Have the Conversation

It is important to have the “I’ve been married before,” conversation. It is critical to have this conversation sooner rather than later so that there are not any secrets. This is fair for both parties. 

For the divorcee, it allows for him to know early on if you can accept this part of his story. For the other person, it is important to know this information before they fall head over heels. 

My boyfriend and I had this conversation before we became an official couple. He was very nervous to share with me, and he feared possible rejection. I genuinely appreciated his candidness not only about why the relationship failed, but what he learned from it.

Addressing Fears and Insecurities

It can be easy to feel insecure when dating a divorcee. You might have doubts or questions about every experience. Further down the road, you might have questions about the engagement or the wedding planning. While certain experiences might be new to you, you might worry that those same experiences won’t be exciting or meaningful for him.

The best way to address this is to lean into the hard conversations. My boyfriend has been very open about his past marriage, and he hasn’t withheld information. I do not pressure him to share anything he isn’t ready to because it was his personal experience. At the same time, he doesn’t overshare and only shares what I ask of him. The further along we go in our relationship, the deeper we dive into past relationship wounds and lessons learned.

We each do our part to create our own memories and to leave the past in the past. While he may have had some experience that I have not, he has never had these experiences with me. So in many ways, these experiences are new to him too. 

In general, both my boyfriend and I have lived full lives before we met each other. There’s a lot of lessons learned that comes with that. As we walk down this road together, we work together to take the nuggets of wisdom with us while letting the past stay in the past.