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Dear Damon,

I met my husband in high school. I had our first kid my junior year, as a result of a fling after we had left our high school sweet hearts.

We broke up right before I found out I was pregnant. While I was hospitalized (water broke prematurely) he called me everyday and asked if I’d take him back. He had went off to college to play football and we were together long distance.

During that time a lot happened, I was homeless at one point and moved to where he was for a better life. 4 years of marriage and a second child later, I found out he dated someone for about a month (they only went on one date) while I was away. And he still maintained an on and off relationship with his high school sweet heart.

Sometimes when we’re really going through it he would contact her and do the whole “what if” thing and then blame it on drunkenness. I feel like I was just the plan B girl, because of our child together, and because we’re so young I always hear comments about how I trapped him (which I would never do). I just want to know why he would stick around so long if he had feelings for his ex or wanted to see other people. Did I trap him without even knowing it? He’s a great looking guy and played football so he has no problems getting anyone he wants… Just wondered why he would stick around if he really wanted to be somewhere else, knowing I would let him go if that’s what he wanted. Sorry this was so long I felt I had to explain everything in detail.


The high school fling that turned into the real thing



Dear High School Fling,

For several months last year, I was working on a side project with a few friends. I won’t go into any details, but we had a great idea, a great plan, and were committed to executing that plan. But, a couple months or so into the project, something just didn’t feel right. Didn’t know exactly what it was, but things didn’t feel the way we expected them to, and weren’t progressing the way we wanted them to. The simple decision would have been to just regroup and start over, but it was almost like none of us wanted to admit what was happening wasn’t working, because we had to much time and thought already invested in what we were doing.

In business terms, this is known as a sunk cost. This mindset, however, applies to many relationships, where good and well-intentioned people stay with each other just because they’ve already invested so much of themselves into it. What eventually happened with us — and what needs to happen with you — was a “come to Jesus” conversation where we finally admitted that things weren’t working and needed to change. Because as much as we wanted to respect the time we already put into that work, we were losing even more time — and wasting effort and energy — by not changing things. Fortunately you’re both young and literally have your entire lives ahead of you. And trust me, you don’t want to be having the same  shoulda/woulda thoughts at 45 that you’re having at 25.


Damon Young

Pittsburgh native Damon Young (aka “The Champ”) is the co-founder of the ridiculously popular Their first book “Your Degrees Won’t Keep You Warm At Night: The Very Smart Brothas Guide To Dating, Mating and Fighting Crime” is available at   
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