Once upon a time in my twenties, I was Condola, the new character Lawrence is dating on this season of Insecure. She is Lawrence’s love interest, unbeknownst to Issa, who has developed a business relationship and personal rapport with her. When Issa finds out they are dating, she decides to continue working with her. Molly advises against it, and although things are not the best between the besties, her thoughts do have some merit. I know this from experience.

My experience was very similar to Issa’s. I was out and about, met and connected with a beautiful, sweet, astute and cool as shit kindred spirit. It was in a professional capacity, but I could tell we would probably also become friends.

We were both new educators, she had already been teaching for a year, so we started meeting up and chatting on the phone about lesson plans, best practices, night life and other common interests. I am pretty private about my personal life, especially when meeting new people, so I hadn’t divulged details or even the name of my new boyfriend. I did however, mention her to him in conversation a few times, and after a few weeks of talking about her, he asked more questions and discovered it was his ex-girlfriend.

Pause. What is a girl to do?

It was very awkward initially, but we actually worked through it. Or, so I thought.

Like Issa, I immediately said I could handle it. I was mature. We were mature. They had broken up almost a year prior and our situation was new and going well. So, although I had some reservations about it, I continued building a rapport with the ex-girlfriend. I talked about it with them separately and she and I agreed to just keep our dealings with each other strictly professional.  He and I decided to not discuss my conversations or outings with her.

This went on for about three weeks before I discovered they had reconnected behind my back. When I talked to him about it, he told me they realized they still had a thing for each other and they chose to explore it.

I don’t have any regrets because I know I can’t control what other people do. That situation taught me I was dealing with two people who were comfortable with being deceptive and who probably needed closure or togetherness. Either way, they did me a favor by showing me I didn’t need to be with him or be friends with her.

Looking back on it, I should probably say do not become friends with the ex of your current partner, but I believe it is on a case by case basis. It depends on so many things, including your level of feelings for that person (should be none), how serious the relationship was, maturity, and willingness to communicate and be open and honest about how you feel, what your boundaries are and what you want.

What can you handle? Can you really have a real friendship? Is it organic or forced?

I think it’s commonplace for this dynamic to develop when it comes to blended families because if the relationship is serious enough (marriage, long-term), you are raising children together to some degree. Whether you are the ex or the current, you have to ask yourself if you can handle it, set boundaries with your spouse and friend and make sure the friendship is organic and not forced.

I’ve had friendships develop through stranger things. It happens. Just make sure it’s authentic and it works for you.