The Biggest Mistakes I Made When I Started Dating After Divorce

Dating after divorce can be scary but also exciting. It’s a chance to meet new people, rediscover yourself, and potentially find love again. But in hindsight, I made a few mistakes that slowed my progress and added unnecessary stress to the process. Here’s what I learned, and what I’d do differently now.

I Was Overly Concerned with What People Thought

I didn’t like the idea of people in my area knowing I was dating. The thought of exposing myself, especially to those who knew me before my divorce, made me hesitant. As a result, I probably didn’t meet as many people as I could have if I had been more open.

What I’d do now: Dating after divorce is incredibly common, and there’s no reason to feel self-conscious about it. While I’d still maintain some privacy, I wouldn’t let fear of judgment hold me back from putting myself out there.

I Didn’t Ask My Friends to Set Me Up

It felt embarrassing to admit to friends that I was actively looking for someone. I saw dating as a private journey, and I didn’t want to burden others by asking for introductions.

What I’d do now: Like Charlotte in Sex and the City, I’d reach out to friends and see if they knew anyone I might connect with. Even if nothing romantic came of it, expanding my social circle could lead to meaningful friendships or new experiences.

I Agreed to Dates That Didn’t Interest Me

Too often, I defaulted to the standard coffee shop or restaurant meet-up, essentially an interview in disguise. These dates felt repetitive and didn’t always allow for a real connection.

What I’d do now: I’d prioritize activities that genuinely interest me. A shared experience, like going to a museum, taking a cooking class, or attending a show, would have made the date enjoyable even if there was no romantic spark. I’d also pay attention to whether the other person was open to stepping outside their comfort zone to try something I enjoyed.

I Let Rejection Get to Me

If I thought the date had gone well but the person didn’t pursue things further, I’d overanalyze it. I’d wonder if I had said something wrong or if they had judged me in some way. I focused too much on whether they liked me instead of asking myself if I even liked them.

What I’d do now: I’d keep my focus on my own life and interests instead of placing too much emotional weight on someone I barely knew. Early-stage dating should be a small part of your life, not the main concern. If someone isn’t interested, that’s fine, it’s simply not the right match.

Final Thoughts

Dating after divorce is a learning process, and mistakes are part of the journey. What matters is recognizing what works and what doesn’t. If I could give my past self advice, it would be this: don’t be afraid to put yourself out there, prioritize experiences you genuinely enjoy, and remember that your time and energy are valuable. The right person will respect and understand that.