Very First Date After a Divorce

by Molly Undercover on May 17, 2017


To date post divorce you just have to dive in.

In her famous Ted talk on vulnerability, Brené Brown says, “vulnerability is. . . the first date after a divorce” I couldn’t agree more. I was terrified before my first date! Three months after my husband and I separated, I wasn’t looking for someone to date yet. I felt repulsed by the idea of being in a relationship again and hopeless that I’d never be able to connect with a man again. But I was also worried that if I passed up dates, I’d calcify and never get back in the game. I did miss romance, for sure. When someone cute but not ‘my type’ asked me out, my fear of becoming a lonely cat lady if I didn’t start dating pushed me to just try it and see what happened.

And then the first post-divorce date finally happened…

Over text messages, I awkwardly informed him that he was a true rebound. I was just looking for fun and flirtation. He reassured me that fun was the whole idea. Putting me at ease, he stated that he’d probably be a awkward when we met because he thought I was gorgeous! I got excited. I arranged for my son to go home with a friend so that I could meet him for a patio happy hour one afternoon.

We met at a fun neighborhood bar. I was still nervous that he might expect something. I just wanted to flirt. I was excited to show up and trying something new.

We were the only people there, which amped up the awkward feeling. But contrary to his warning, my date was actually laid back and fun, totally confident, and looked and smelled great. He put me at complete ease.

As we played giant Jenga on the patio, his confidence and masculine presence infused me with my own confidence. He was starting to get a little handsy. Brushing my wrists and finding other ways to make contact as we goofed around and talked. He was making me laugh and dammit, this was fun! At one point he leaned in for a kiss. Nervous and feeling vulnerable, I did the old ‘cheek turn’ trick and let him plant one there. Then I changed my mind, and we kissed. OMG. I was kissing a man! I had almost forgotten how fun it felt to kiss. And I had thought this would never happen again.

We enjoyed each other’s company for a little while, then I had to go and pick up my son. I went from feeling closed off and hopeless that I’d ever date again to goofing around with a sexy man on a patio on a sunny June afternoon. If you’re like I was and a little scared to try out dating, know that it can be fun!

Based on what worked well for me about this, here’s my advice for the first date after becoming a single mom:

  • Be clear with him upfront if you’re on the rebound!
  • Obviously but worth stating: have your own way there and home and let someone know where you’ll be.
  • If you’ve been in a relationship for a while: don’t turn someone down because they are not ‘your type’. Someone very different might be just the thing!
  • Plan to keep it short. Happy hour or coffee when you’ll have to pick up your child is one idea. Your time is so precious as a single mom and realistically, you may not see this person again.
  • Just be yourself.
  • Be easy on yourself. You don’t have to meet prince charming on your first time out after marriage and parenting.
  • Remind yourself to be open and not compare your date to your old relationship. They are two totally different situations for many, many reasons.


Ms. Single Mama II , aka Molly Undercover

{ 2 comments… read them below or add one }

Hanna May 22, 2017 at 11:35 am

Welcome to Single Mama dating! I’m 3 years into my post-baby daddy relationship, and it’s going well. Vulnerability and risk are some of the scariest things to embrace, especially when it involves you kids! Good Luck and Brave On!


Molly Undercover May 24, 2017 at 5:21 pm

Thank you so much for your encouragement and kind words!!


Leave a Comment