Love/Life: The “What If” Guy


Watching HBO’s hit show “Insecure,” I couldn’t help but to think about my own experience as a young black woman navigating love. In the series, Issa (the writer and main character) is in a relationship with Lawrence (played by the handsome Jay Ellis)…but as Lawrence attempts to figure out his career, Issa’s ex–or “what if” guy–pops back in her life.

It made me reflect on my own “what if” guy, a guy I had dated in college. I believe all straight women have one–that guy they think about often, wondering what could have been: What if the timing was right? What if we really gave it a shot? Where would we be now? 

My “what if” guy? We didn’t go to the same college, but somehow connected. I would go to his football games, he would come back home to hang out. At points, we would not talk for months. At other times, we were talking constantly. After he graduated, I broached the idea of a serious relationship. He dismissed it, so I let our “situationship” go.

We both entered into other relationships, only reconnecting through likes on social media. One night, he called me drunk at 1 a.m., asking to hang out. I declined, knowing it would disrespectful to my current relationship, but he went on to express his real feelings for me–feelings I never knew existed. We talked for a while, acknowledging that we were both in other relationships.

Unfortunately, the conversation didn’t end that night. We texted constantly that week, discussing the great college memories we shared…and that lingering “what if” remained in my mind.

What if we could’ve made it work?
What if we would’ve just told one another how we felt instead of playing it cool?
What if the perfect story I had in my mind about us could come true?

Eventually, he asked me if I thought our chapter had ended, and I told him I did. His response shocked me: “I don’t think it has,” he said. “If it had ended, we would not be having this conversation.”

I paused before replying, meditating on his words as if they were a Bible verse. I thought about my current relationship and the man I had spent the last two years with. He was nothing less than amazing. We had our disagreements and arguments but he treated me the way I deserved. He showed me he cared about me. I never had to guess how he felt about me. I loved him and I knew he loved me. The feelings I had for him was stronger than any feelings I had ever felt.

So why was I dwelling on “what ifs” with another man?  In the words of Issa, “[he] was an itch I needed to scratch.” I had created this idea in my head that we would be in a relationship after college, get married, have kids, live happily ever after. Though I had started a life with someone else, the thought of realizing that dream after all these years seemed magical.

But it was just that: a thought. It wasn’t about him or who he was, it was about the idea of him. It didn’t work out for a reason. The same lack of expression during our “situationship” would continue in a relationship. And the real love I had for my boyfriend superseded any idea. We were not meant to be. 

I realized, too, that he was right. By texting and talking to him, I was proving that our chapter was not over. So I told him that we were indeed over, that he should give his girlfriend his heart. I no longer needed to scratch that itch. I didn’t need a “what if” guy–I had a “what is” man.


Do you have a submission about love, life and everything in between? Submit your post for Love/Life to Jessica Gregg, STYLE’s managing editor, at [email protected].

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