I’m Dating a Man Who Dated a Model and I’m Feeling Really Insecure.


The man I am involved with is a fashion photographer, whose latest ex is a model. I am in general quite self-confident (I have a great career that I love and have been dreaming about, and in general am happy with everything else in my life), but I am starting to feel inadequate about our relationship, or rather, how he sees me and why he is with me. I don’t look even close to how models look and I don’t want to look like them, to be honest. I have always been comfortable in my skin until I met him.

Now all I can think about is how he sees me and all my imperfections, which are many – I’ve gone through many surgeries and other related medical treatments. This has given me strength and taught me to love myself, but it certainly left its marks on my body. His involvement with models bothers me and most of his friends are from the industry. I believe that since it’s just the beginning, it’s probably easier to end the relationship not to hurt anyone in the future. But something stops me as other than this, he’s everything I’ve always wanted in a man. I am scared to bring it up with him as I don’t want him to think I am not the self-confident and strong woman he thinks I am, and I obviously don’t want him to quit his job or to unfriend anyone, as it’s his life and his choices. What would you advise in this situation?


Once upon a time, there was a very confident dating coach. He had gone out with hundreds of women, hooked up a decent amount, and never had any doubts about getting a second date (Of course, he was wrong about 20% of the time, but that’s neither here nor there.)

Then, one day, the dating coach met a SEX coach. He was flummoxed. Not that he was previously insecure with his performance in bed, but, really, a SEX coach? Belying his experience, he interviewed the sex coach like an insecure, needy intern, and although they did hook up (he’s proud to say), he was EXTREMELY self-conscious about the entire thing (and somewhat surprised that she was so selfish in bed.) They did not continue beyond two dates — largely because of his insecurity. He simply wasn’t confident enough to be himself around her.

99% of us are NOT models.

That’s personal anecdote #1. Here’s a similar story from the other side — your letter reminds me of an ex-girlfriend of mine who used a similar line of thinking to justify breaking up with me:

“You like looking at models. I don’t look like a model. You must not be attracted to me. I’m going to make a big deal about the fact that there are more attractive women on Earth and ruin what was previously a great relationship over my own insecurity.”

So let’s get this straight, Lainie:

I have no idea who your fashion photographer guy is — whether he’s the guy you’re “involved” with, which might just mean he’s fucking you, or whether he’s a “boyfriend,” which means he has committed to exploring a long-term relationship with you. But I do know this:

99% of us are NOT models.

I have never walked into a party and felt like the best looking guy in the room. I’m okay, but my self-esteem derives from my intelligence, my wit, my moral compass, my heart, my sensitivity and so on. I realized that I didn’t have to win a beauty contest with all other men. I just had to really, really like myself — to the point that I never worried whether women would like me.

It was that CONFIDENCE — not intelligence, money, or looks — that served me well for 10 years and 300 dates. And it’s that same confidence that will either allow you to recognize that you’re a prize for this photographer…or sabotage it with your own insecurity.

Put it this way: if he’s with you, he’s attracted to you. Case closed.

Put it this way: if he’s with you, he’s attracted to you. Case closed.

What’s going to KEEP him attracted to you is your confident, positive, queen-like attitude — where you can be yourself at all times and realize that if this guy doesn’t appreciate you as you are, it’s HIS loss, not yours.

Don’t break up with him, Lainie.

Break up with this negative self-talk and you’ll be just fine.

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  1. 21

    Due to my dating patterns in the past, I get this all the time from women who worry they won’t measure up. It’s frustrating and a turn off. If I’m with the woman it’s because I want to be–not because I don’t have a better choice at that time.

    Ive always been partial to “blonde bombshell” types–classic 36-24-36.   I also like “taller” women with long legs. So, then if I dTe a woman who happens to be a brunette, or she shorter at around 5’4″ or less, she worries. If I hadn’t thought she was cute, I wouldn’t have bothered to ask her out.

    Women, in my experience, have very fragile egos. They’re also incredibly competitive with one another.

  2. 22

    Lynn– anytime a guy starts telling you how much he’s into you after one or two dates–major red flags. Reminds of the boys in HS or college who did that to get laid not knowing it wasn’t necessary. Or maybe it was for them. Anyhow, when a woman acts like that with me, I run. I’ve learned to know cray cray when I see it.

  3. 23

    on the topic of models, they generally do not look like their pics in real life. They have bodies that are great for hanging clothes on and large faces that are great for painting. In the morning when you wake up, it’s a whole different animal.

    Every once in a great while you may come across one that is a genuine Amazonian beauty. But that’s even rarer than a guy over 6’2″ that doesn’t resemble Lurch in some way.

  4. 24

    My oldest ex dated a woman who was ‘model material’, blond, tall, big boobs, very pretty. im petite, brunette. I had no insecurities because he chose me. i am a confident person and have an engaging persona (when i want to have lol). i am vivacious. i like who i am and most of my personality and ive never had problems getting a boyfriend and neither have i compared their exes with myself. if it was that good theyd still be together. however (theres always an however with me :-), my last ex went with a 23 year old before me (im 45) i didnt feel threatened by her age but i did feel threatened because of my boyfriends actions, he was an immature 36 year old and was better suited to a younger woman, thats the only time ive felt pretty crap because i knew he was better suited to this 23 year old attention seeker (she was trouble btw). However 🙂 i was more mature and i dont think he understood that i questioned our compatibility because he showed signs of being immature and that he was well suited emotionally to a 23 year old ( not generalising oc). He wasnt for me. He also very rarely complimented me. Very superficial.

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