My ex-boyfriend, Philly Matt, and I see each other two or three times a year. In a typical month, we’ll text and email several times a week and talk on the telephone every other week. Even though we haven’t dated since 2006 or had sexual relations (using the definition of Former President Clinton) in four years, we’ve grown closer. He’s my sounding board and one of my best friends.

Several readers and friends in real life have asked why Philly Matt and I don’t try dating again. I felt like it wasn’t worth jeopardizing our friendship for the possibility that we might be able to work as a couple. I was thus very surprised when Philly Matt informed me in May 2010 that we weren’t together because I was always in a relationship or getting over someone.

Thanksgiving 2010 found me in casual relationships with Best Boy and Mr. Agency, and Philly Matt in a serious relationship with Tammy from New England. When I talked to Philly Matt on the phone, he relayed to me how upset Linda, the mother of his children, was at how much time he had been spending with Tammy.

Philly Matt: Linda keeps saying that she might not want to be with me, but that she doesn’t want anyone else to be. I told her [Linda] that she had her chance. She can’t be upset that I found someone else.

I started thinking about how odd this exchange was. Why would Linda care if Matt was dating someone since she and Matt haven’t been together in almost a decade? (When I met Philly Matt in 2005, he said that he and his children’s mother hadn’t dated since his youngest child was a baby.) Wouldn’t Linda want Philly Matt to be happy?

Me: A little jealousy is normal, but it doesn’t make sense that Linda would be so upset about this. You said that she’s been making similar comments about you and Tammy since the summer, right?

Philly Matt: Yep.

Me: Have you guys been together recently?

Philly Matt: What do you mean?

Me: Well, that sounds like comments that someone would make if they still had feelings for you. Have you and Linda been together since Chloe was a baby?

Philly Matt: Yeah.

Me: You have?!?

Philly Matt: Yeah. We’ve been together on and off for years.

Me: Really?!? So…when was the last time that you guys were together?

Philly Matt: We were trying to make things work earlier this year. [My jaw drops, and my eyes become as big as saucers. I want to ask why that hasn’t come up in the past five years, but I just let him keep talking.] We tried, and she said that it couldn’t work between us. I wanted it to, but what could I do? So, I moved on.

My mind was scrambling, and I realized that I needed to collect my thoughts about this. Matt and Linda had started dating 17 or 18(!) years ago. I might not have even dated him had I known this back in 2005 since I would never get between a man and the mother of his children. It also crossed my mind that if I was just finding this news out now, did Tammy know?

I figured it best to change the topic and discuss this more in our next call. It wasn’t pressing since Philly Matt's relationship with either Linda or Tammy didn’t affect my relationship with him. But, it was definitely a game changer and reaffirmed in my mind why Matt and I weren't meant to be more than close friends.