I’ve Maintained a Relationship with My Ex’s Family, and This Is How It Went

Over ten years ago I had my first boyfriend. I went on my first date to the Mandarin where I ended up throwing up a strawberry and making a huge embarrassment of myself. Somehow, he still wanted to date me.

I was 15 at the time and of course thought this high school relationship was going to last forever. I mean, what 15 doesn’t think that about their first relationship?!

Well almost  two and a half years later, that dream came crashing down. We were about to graduate high school and were off on our next big adventure. Sure he was planning on going to a school halfway across the country, but to me that didn’t matter. I didn’t think it mattered much to him either.

Until it did.

I don’t really know what a “normal” high school relationship looks like, especially not ten years later in this day and age. But as far as normal relationships go, I’d say we had it. We hung out almost every day before, during, and after school. We’d have sleepovers once our parents decided we were grown up enough to be trusted (even if I did sleep on a really comfy air mattress beside his bed). We talked about our future, we went to school dances and we said, “I love you” often.

I don’t doubt that he meant it when he said it, and I know I sure as heck meant it all the same. It was one of those all consuming first loves you still think about and reflect on, because how could you not?

I’ve been with my current boyfriend for almost seven years now, and it’s likely we’ll be getting engaged and married in the next couple of years. I’m not about to compare first loves to subsequent loves by any means, but because I still have a relationship and connection to my ex’s family, I think it’s important to note the current state of my relationship. A loving and caring, open and honest relationship, at that.

Sure he might not be totally comfortable with all this, but he takes it in stride. That’s one of the things I love most about him.

Anyway, back to the real reason you’re here. “Vicki, you still have a relationship with your ex’s family?!”

To really understand this, I think we need to learn a little bit more about me.

I am the only girl with four brothers. I did not grow up having a lot of girls around. Sure, my closest friends were girls and we spent a lot of time together. But, other than my cousins who I saw on a semi-regular basis, there wasn’t a lot of female presence around me other than my mom.

So when I started dating a guy with two sisters around my age, you betcha I clung on for dear life.

Sharing clothes? Yup. Need a hair straightener in a pinch? You betcha!

I spent a lot of time with his family, and he with mine. As time went on, they became my family too. But that ultimately meant I was spending more time with him then I was any of my friends.

So maybe we drifted apart a little the longer we were dating. Which made it that much harder when he broke up with me. I remember crying in a car, no idea who to call, and I dialed his older sister’s number for advice. She was there for me.

And in turn, I was there for her. We lived in the same city for university, which resulted in her sleeping on my couch when she didn’t have a place to live. One semester we even became roommates. And then I was a bridesmaid in her wedding.

It’s now been over eight years since we parted ways, but I still maintain a relatively close relationship with his older sister, and to a degree, his younger sister too. To make things even crazier, I’ve even gone out to tea with his now wife! Oh and did I mention I’ve also been friends with his cousin since before we even started dating?!

To the outside world, I know it’s pretty strange. I never really separated myself from that world, which at first definitely made it harder to move on.

What made it easier was that my friendship with his older sister was rooted in something more than us just having him in common. In fact, I wouldn’t even say we were really good friends while I was dating him. Our friendship blossomed as she became apart of my support system, and gradually I was becoming apart of hers.

I think that’s the biggest reason our friendship works out. Sure, sometimes she’s going to update me on his life, because I update her on my brother’s lives too. My older brother was even a bartender at both their weddings because they liked him so much. Because that’s just what friends do.


Separating your friendships from being only connected by your ex is deeply important in maintaining a relationship with them that won’t drive you, or your future partners absolutely crazy.


As cliche as it is, time plays a huge factor in it. When I was first hanging out with his sister after we broke up, things were still very raw and it reminded me of him often. Maybe it slowed down the healing process or gave me false hope, but overtime I think that friendship really helped me move on and grow to love someone else.


If this is a relationship that you truly want to work, you have to realize that time will definitely play a great role in how your friendships grow and develop over the years. I’m at a point in my life where friends that don’t live in the same city as me are somewhat drifting apart. That’s just apart of life, but it’s definitely something I’ve notice when it comes my relationship with my ex’s older sister. But with time it’s become just that, another friendship that has its challenges, but comes together nicely when we’re actually together.


When it came to maintaining these relationships, the hardest part was definitely interacting with their mom. Their mom had definitely become a second mother to me throughout the time we dated, and after we broke up, she didn’t treat me any differently.


We saw each other on a semi-regular basis, especially a lot during his older sister’s wedding. I was over at their home a lot helping with DIY projects and whatnot. And despite it being years later, and me having a long-term boyfriend I loved very much, it almost felt like nothing had changed.


Over the years I had come to realize my own breaking points in these relationships. Where I could maintain a healthy relationship with his sisters on the regular, maintaining one with his mother was definitely out of the question. It made things too familiar, and put me in a new reality of uncertainty.


You need to make sure you know your own boundaries and limits. Just because you can maintain a relationship with some of the family, doesn’t mean you have to do it with all of them. And even if you can’t maintain a relationship with them right away, doesn’t mean you won’t find your way back to them. True friendships often have a habit of doing just that.


It’s funny that I’m writing this essay when I am, because I’m actually heading to a family party of theirs this weekend. And they’ll all be there. But so will a bunch of my favorite girls from high school who were with me all the way, and still are to this day.


For those of you who feel like you’re losing your family when you’re splitting with an ex, don’t feel that it has to be that way. There are definitely ways to maintain a relationship with their family in a healthy and mature way. Sometimes they might be your biggest support system, and greatest cheerleaders along the way.


I don’t have a lot of ex’s in my life, but the only other one I have, plays softball with me every week. Trust me, life’s funny that way.