How I Married My High-School Ex (After 11 Years Of Me Wanting Him And Him Not Wanting Me!)

I want to finally share the story of how I married my high-school ex-boyfriend after 11 years of me wanting him and him not being interested in me at all!

I’m not super comfortable being so open and vulnerable (I’m an Aquarius, after all!), but I know my story will resonate with most of you and it will help and inspire you so I’m going out on an emotional limb even though it terrifies me a little. 

The reason it’s taken me so long to share the story is I can’t tell it in a vacuum. In order to fully understand how I was finally able to have a healthy, stable relationship for pretty much the first time in my life, you need to know a little more about me and my past relationships. 

OK, so let’s begin. 

So growing up I wouldn’t say I was “unattractive” but for whatever reason, I was an “undesirable.”  I realized it around my tween years, so maybe like age 10 when boys and girls started really taking notice of each other and I was never wanted. 

I can’t totally put my finger on what it was, maybe because I was always so much taller than the other girls? At the time I felt like a big fat hideous monster, but when I look back at pictures of myself during that time I wasn’t at all! I was actually really cute, but I got annihilated for my appearance, especially by boys. 

I was in the popular clique- so my best friends were the prettiest ones who all the boys liked, and I was always the second fiddle. I wasn’t a threat to anyone because I was so undesirable, I was just the supportive friend who was there to listen to all the boy drama they were experiencing. 

My best friend was the queen bee of the group and it was really sad because anytime I would have a crush on a guy, it would turn out he was desperately in love with her. And this happened every time. 

I got made fun of a lot, I got called fat a lot even though I wasn’t. I felt horrible about myself and that led to a lot of self-loathing. I developed an eating disorder at age 12 and it was on and off until 17. 

When I was 17, it got really bad and I was hospitalized for a month. 

When I got out of the hospital, I was healthy for the first time in many years… and all of a sudden I was getting all this male attention, and it felt surreal. 

It started slowly. All of a sudden guys started taking notice. Up until that point I had so much shame around my lack of desirability. I felt invisible, and when I wasn’t invisible, I just felt like I was too much, too grotesque.

I got out of the hospital at the end of March and I met my husband in mid-June at a party. 

I gave you this background because our childhood basically sets the foundation for our adult relationships, so this part will explain a lot of what came later. 

OK, it’s June and the end of my junior year of high school and I’m at a party and meet the man who would become my husband. 

We meet, we talked, we flirted, we kissed. And I was flying. I remember feeling this electricity running through my body, nothing I’d ever felt before. 

He got my number and I was ecstatic- in my mind it meant we were going to be boyfriend/girlfriend because that’s how it always goes in the movies… but he never called me. I was understandably really hurt and really confused but I was also very distracted by the copious amount of men who all of a sudden did want me. 

I’m telling you this just to illustrate how confusing and absurd my life was- I had no idea who I was or what the world thought of me because for my whole life I was told one thing, and now suddenly I was being told another. And I had no sense of self to fall back on- I was letting everyone else tell me who I was and it was utterly confusing. 

I felt like it wasn’t real, like I was in some sort of dream. 

But I loved the attention. I also didn’t know how to handle it. I was on this endless hamster wheel just desperate for validation, and no matter how much I got, I desperately needed more more more.

My good friend’s boyfriend’s mom was a caterer and she was looking for some waiters to help out with events on weekends. My friend asked if I wanted to do it, and I didn’t at all, but then she told me the other guys who were going to be doing it and the boy from the party happened to be one of them, so I was like: Sign me up! 

My plan was simple- look really hot and ignore him and make him rue the day he decided to get my number and never call me. 

And I really handled it perfectly. I looked amazing, and he saw me walking over to put napkins on a table. He was staring at me intensely, and he walks up to me and said, “Hey, how’s it going?” And I casually glance in his direction and say, “Good” with a sweet little smile, and then I walk away. 

It didn’t take long for him to actually utilize the phone number that he had added to his contacts so many months ago and we were talking and texting (and of course, talking on AIM, this was the early aughts!) daily.

He was a year older so he was a freshman in college but his college was 45 minutes away so we were able to see each other. 

And I fell for him, HARD. 

At this point, there were guys who desired me, but none of them knew me.

Having someone who actually, genuinely seemed to care about me was just so unbelievable. And I honestly think I really loved him, although I know he didn’t feel that way about me at that point. 

Our relationship wasn’t serious by any means, but it was very significant, at least to me. 

So this went on for a few months and then I decided we should have “the talk” to define our relationship.

I had a whole council meeting with my friends and we decided that I should be straight up and ask him “What are we?”

So I waited until the next time we were together in person and I just went for it. And he went white. He fumbled over his words and said “Uh, I guess we’re just hanging out?”

And I was actually OK with that, I wanted to be his girlfriend but I didn’t care that according to him we were just “hanging out” because I just wanted him in my life. 

But after that, he wasn’t anymore. I just stopped hearing from him completely. 

And I was gutted. I mean beyond. But I didn’t reach out… at least not yet. Weeks went by and I didn’t hear from him and then I found out he was telling people it was over between us. 

And I was crushed. I never felt such levels of despair in all my 17 years. I confronted him and he said he didn’t want to be serious with me and he could tell that’s what I wanted. I remember him going off about why do girls always ruin things by wanting it to be so serious? 

And I tried telling him I was OK with it being casual but he was basically like, no you’re not. It’s done. 

At that point, I was interning at US Weekly Magazine which was a really cool experience. My high school had an internship program for second-semester seniors and by a stroke of luck I ended up there and what I remember most vividly was taking the train into New York city every morning and evening and replaying every interaction with him over and over in my mind (to this day I can recount conversations we had back then verbatim and he thinks I have a photographic memory but it’s just because it was a tape played on loop all day every day for many months!). Everything I said and he said and as I sit here right now telling you this story, I can feel that blade in my heart again.

After a few months of obsessing and dwelling and crying, it was clear to me he wasn’t coming back. So I tried to move on. I found a new guy we’ll call James who was really hot, but he was a garbage dumpster fire of a human being who treated me horribly. 

He was a raging narcissist and just awful. I honestly blocked out a lot of my memories of him because he was so terrible. He wasn’t physically abusive but he was extremely emotionally abusive and I just took it. I took it because I honestly thought that’s how I deserved to be treated. And he was very hot and to me, being with the “hot guy” was so validating, it fed something in me and that was enough to keep me around. 

 Me and him had a few breakups, one of them by the girl he was cheating on me with texting me from his phone to let me know me and him were done. 

That relationship did a number on me psychologically, and I was already in such a fragile place. 

Fortunately, I went away to college in Boston so that was the end of him, even though he tried repeatedly to get back in my life for several years. And like any naive girl with zero self-esteem, I did let him back several times, but I was mostly done with that mess. 

College was fun- I partied hard, I continued to live for the attention, I was just like a little girl lost trying to find her way and figure out her worth. It looked like the time of my life on the outside, but when I reflect on that time all I can feel is this emptiness that existed within me.

OK, moving on. My Junior year is the year I decided I wanted a boyfriend. I needed a boyfriend. And a few weeks into the school year, I met Eric Charles- yes, my business partner on A New Mode.  

Just like with my ex, when I met Eric I had this overwhelming feeling that this person was meant to be in my life. And my instincts were right. But Eric and I were not meant to be a couple, at all.

So I won’t get too into the details of my relationship with Eric because I’ve written about it a lot over the years.

The fact is, he and I were both two broken people trying to hide from our brokenness. And it was nice being together so that was a distraction. He wasn’t in a position to be in a relationship and neither was I really. I was just a lost puppy starved for love and he couldn’t give it at that point, and he told me so! From the beginning, he told me he didn’t want to be in an official relationship but I stayed anyway even though it killed me inside. 

And we did love each other and we did spend literally every waking moment together but it wasn’t a healthy relationship, and it wasn’t even an official relationship. The fact that he wouldn’t give me that title just confirmed my long-standing belief about myself- I wasn’t worthy of love. I was damaged and unlovable and I better take what I can get. It’s this or nothing. 

So that relationship ended after about a year when he left me for someone else and I was devastated. Beyond devastated. I felt like I had been gutted from end to end. I felt like an essential organ has been ripped out and I could no longer function. 

I didn’t properly cope with the grief and the trauma of it all and instead, I went cold- I just turned my emotions off. I numbed myself out. 

By my senior year of college, I became a self-proclaimed Maneater. I would go out and find the hottest guy in the room and make him ache for me, just for the fun of it. 

Now up until this point, I was always the one being treated badly, but after that, the roles were reversed and I was just awful. Any guy who dared try to love me or date me, I was just awful. I was mean and cold and selfish. 

After I graduated, I moved to New York City and started working as a fashion and beauty editor. I was living a really cool and glamorous life. I was going to Fashion Week and awards shows and interviewing celebrities and getting tons of free stuff and I had an amazing group of friends and my life was fast and fun. 

I was mostly focused on work and with the guys I dated, I was either not interested and acted cold and aloof, or I was desperate and needy. 

I met this guy named Kyle who I did really like, and at first he really liked me, but then the relationship devolved into what my relationships usually devolved into– it was me being super needy and him calling all the shots and me just trying to make him love me. 

I could write a whole other essay on him and the lessons learned by the TLDR is this: he started distancing himself and pulling away, I tried everything to get him back, and he ultimately ghosted and then called me a few weeks later but he wasn’t calling me… he meant to call the new girl he started seeing. 

At that time, my roommate sublet her room to this incredibly hot guy who was my roommate for a month, and living with him is actually how I started gaining all my insight into men. After that fateful call, he and some of his friends sat me down and explained everything about the relationship and where it went wrong.

And I actually felt better after hearing the honest truth. I didn’t even feel the need to obsess and spin my wheels… and I was the queen of that!

I also remember thinking: this is what the world needs, the world needs to understand how men think as told by actual men. 

Fast forward a few years later, I got back in touch with Eric and in an attempt to get him back I tried making him jealous by talking about all these guys who were after me… it didn’t have the intended effect but instead, Eric suggested I write about this and share my knowledge with other women and that’s how ANM was born back in 2009!

I really committed myself to understanding personal development and relationships. I became the go-to guru for all my friends and many of them will tell you that I’m the reason they were able to have success with men and relationships. I was really good at understanding relationship dynamics and I made it my mission to understand men and women and how they relate to one another. 

Things were starting to look pretty good for me and around this point, my parents had a charity event at our house and I vividly remember turning a corner and suddenly being face-to-face with my high school ex. 

I literally went weak in the knees. 

He looked at me, shocked, and asked: “What are you doing here?”

And replied, “I live here. You’ve been here!”

And he said, “I thought this house looked familiar.” 

Our conversation was super brief because I legitimately felt like I was going to faint. I just couldn’t talk to him. I went off to some other part of the house and our eyes would lock from across the room but that was it. 

The next night he messaged me and we talked for hours. We basically caught up on what we’d been up for for the last five years plus. And he kind of apologized for what happened in the past without directly doing it. He told me how he had changed, how he used to be a selfish terrible person who didn’t think about other people. Umm yeah, I know! 

And that night I was convinced we were getting back together. I was absolutely ecstatic. 

But it didn’t happen … I didn’t hear from him again after that. 

Time marched on and I really started getting a grip. I started seeing an amazing therapist and really getting to the heart of some deeply rooted issues. I finally developed some self-respect and learned how to have some boundaries, 

I took a very long hiatus from boys and dating and just focused on me. 

I think it was about two years later, I ran into Mr. Ex again, this time halfway across the world! I saw him, and I got this feeling that just came over me, I thought, I’m going to marry him. I know I am. 

So we talked a little and he messaged me, but he didn’t really seem to have any interest in getting back together with me. We would talk a little here and there, but then it fizzled out. 

A year later, I ran into him again. This time in my hometown. But this time, he wasn’t flirty or warm to me at all. It was just, “Oh hey- how are you?” In the past our interactions were always full of intense chemistry, but this time it wasn’t there. I found out much later that he had a girlfriend at the time. I just thought he wasn’t interested in me which was devastating because I still desperately wanted to date him and was still carrying an almost decade-long torch for him! 

A month later I met a guy who I fondly refer to as Kevin the damage case. If you’ve been a reader of mine for a while, you know all about him because I’ve written about him a lot. He is a classic example of a guy who just won’t or can’t commit, and my behavior toward him is a classic example of what many women do when faced with these kinds of guys. 

I’ll give you a quick summary here. He and I had a lot of mutual friends and someone set us up. We went on a few dates and then he dumped him. I was devastated because he was the first guy (aside from Ex), that I really liked in a long time.  He and I did this dance for a full year where we would run into each other, things would start up between us, then he would disappear. 

Every few months I would see him, and this would happen and every time I would be crushed. What do they say about insanity? It’s doing the same thing over and over and expecting different results? Well then, you could say I was totally out of my mind at this point! 

Now this one really got me because I knew better at this point. I was a really successful relationship writer. I had bestselling books on relationships. And I was still playing this game! I honestly felt like a fraud but I couldn’t help it. I just wanted him so badly. 

It all came to a breaking point that June. It was so clear to me that while he liked me and was attracted to me, he couldn’t give me anything. And I realized with crystal clear clarity what I was doing and why. 

I was still that 12-year-old girl who was home alone on a Saturday night while all her friends were at the movies with their boyfriends. I was still that girl who was voted ugliest girl in 7th grade by the popular 8th-grade boys. 

I didn’t feel worthy of love because my most significant relationships were with guys who wouldn’t call me their girlfriend. 

I would chase after these gorgeous, emotionally unavailable guys because getting a hot guy validated me, it told me I was no longer that sad undesirable girl from middle school. 

I tell you guys this a lot- the subconscious is always looking to prove itself right. If you believe you are unworthy, you will seek out relationships that confirm this. And that’s what I did. I dated plenty of good-looking, wonderful, emotionally available men who treated me so well, and I was repulsed by them. I thought something must be wrong with them. 

It wasn’t them. It was me. I was the damage case. 

Once I saw my patterns for what they were, once I saw what I was doing and once I saw Kevin the damage case for who he truly was, it lost all appeal to me. 

Now I didn’t grow a sense of worth overnight. I worked on myself. A lot. 

I spent that entire summer living my best life. I worked out, I spent a lot of time writing, I spent a lot of time with friends, I traveled. I was just so on top of my game and so thoroughly, truly, genuinely happy. 

At the end of July I was walking in Central Park with my friend and she was really upset about a guy and I spotted Mr. Ex talking to this girl I also went to high school with. And I told my friend, we have to go over there. I only run into this kid like once every few years, I have to say hi!

So I dragged her over, and I pretended I was going over to say hi to the high-school girl, not him, and then pretended to suddenly notice him.  “Oh hey, I didn’t even see you there!”

Then he and I started talking and our chemistry was back and stronger than ever and I walked away feeling confident I would hear from him. 

Finally, after all these years our stars had aligned. We were both living in the city, both single, both settled in our lives … but I didn’t hear from him. 

So I decided to reach out. I messaged him on Facebook and he was friendly and receptive, and I opened the door wide for him to ask me out … but he didn’t. 

But this time I wasn’t devastated. I was fine with it. I just figured he’s not into me, if he is, he knows where to find me. 

So I continued being my best self. And I had an amazing summer. 

At the end of August, I went to Italy with a friend and while there, I noticed he started liking my status updates, which he had never done before. 

I had a strong feeling he was thinking about me … that he wanted to ask me out … that I would hear from him as soon as I got back into town. 

My friend thought I was being delusional but lo and behold, two days after we got back he messaged me and asked me to grab a drink and catch up. 

I honestly didn’t even know if it was a date or not but I was so nervous all day. Like couldn’t eat, couldn’t focus, couldn’t even walk in a straight line or take a full deep breath nervous.  

Our date was seven hours long and while I was very excited about the possibilities, I really tried to reign it in. 

On our second date, I think we both knew we were going to get married. I remember him making some comment about how we should try to move slowly because this did just seem so right and so perfect but we should try not to get too swept away too fast. 

And then I did what I tell you all to do- I kept my options open. I did not want to fully invest in one outcome. Did I desperately want it to work out with him? Yes! But I did not want to set myself up for heartbreak. I had been through enough of that already. 

So I was still talking to other guys and keeping my options open. But I didn’t do that for very long because we were an official couple within like a month, and he told me he loved me I think in the second month. 

And I wanted him and I loved him, but I was also so scared. I had never been in a reciprocal relationship. I had never been in a healthy relationship. The night after he told me he loved me I started panicking and trying to figure out what was wrong with him.

And I tried pushing him away, I tried sabotaging the relationship. 

But here’s the thing. When a man truly loves you, it will take a hell of a lot to talk him out of it! 

The thing is, love will bring up all that is unloved within you. And it was bubbling to the surface. But I was honest with him and vulnerable and we worked on it together. He told me that nothing I could do would make him stop loving me. I could stab him in the chest and he would still love me. 

But I didn’t put it all on him to validate me. I really worked on it myself and it wasn’t easy. 

We got engaged after six months of dating and married six months after that. Our wedding was actually one year to the day from our first date the second time around- that was just how it coincidentally worked out. 

And we now have three delicious children, the product of over a decade of back and forth and heartbreak and healing. 

Our relationship is far from perfect because none of them are, but I know without a shadow of a doubt I am with the person I am meant to be with and there isn’t anyone I can imagine doing life with. 

I look back on all those other guys and I realize how miserable I would have been with them. Life isn’t just excitement and having fun. That was great when I was single, but when you settle down and have kids, you need stability and security. You need a guy who is a good person and a good dad and I found all of those things. 

Now a lot of you ask what made him change his mind and want me after all those years. 

And believe me, I asked, but he doesn’t really have an answer. According to him, he just thought about it a little more and it made sense. Before that, he just saw me as a girl he dated in the past and it didn’t work out so that was that. And that’s how a lot of guys think. 

I have a different theory. I think my vibe just shifted. I was no longer that desperate, needy woman he once knew. I finally had a purpose and a sense of self and I was genuinely happy. I think that’s what drew him back in. It wasn’t just the same old thing. This time I was someone different. 

Also, we can’t discount timing. But the right person at the wrong time is the wrong person. So over those 11 years, we just weren’t ready for each other. We both had to grow individually. And you can’t control timing… all you can do is clean up your side of the street and get yourself to a solid, healthy place so you can have a happy, fulfilling relationship.

So that’s my story. 

And the moral of this very long story: Work on your feelings of worth. Work on recognizing and realizing that you deserve to have what you want in life. Recognize your faulty patterns and deal with them because your mind isn’t going to re-program itself.

Do this, and you’ll get where you want to go, I promise.