Are thoughts of your boyfriend’s ex keeping you up at night?

Is there a part of you worried about your boyfriend’s ex, and threatened by their relationship?

Worried that your boyfriend might be “settling” for you?

(Transcript below)

When you think of the word “settling,” what comes to mind?

“Settling down?”

“Settling for someone?”

“Settling in?”


When I hear the word “settling,” I cringe.

To me, “settling” in the context of relationships implies a choice to be OK with OK. To “settle” for mediocrity. To “settle” for someone who isn’t worthy of you. And, to rob someone else of the chance to be with someone who’s a better fit for them.

The phrase “settling down” might be even worse. I don’t ever want to “settle down.” There may be marriage, kids, etc. in my future, but you won’t ever catch me using that expression in conversation, even if I have the white picket fence, 2.5 kids, minivan and all the rest some day.

Maybe I’m just a strange guy OK, I’m definitely a strange guy, but the word “settled” is too limp, too uninspiring for me.

I have another question for you…

Would you ever “settle” for someone who is “settling” for you?

Would you choose to commit to someone who doesn’t see you as the absolute best fit for them?

Would you be OK with being someone’s “second choice” for a partner?

Maybe I’m not so strange after all, because I think most of us don’t want to “settle,” or for others to “settle” for us.

Most people don’t “downgrade” when they seek a new romantic partner. Most of us (hopefully) are growing into better, more self-aware people with each passing day. Thus, it logically follows that when we seek a new partner what we really want to do is “upgrade”–or, in other words, find someone better suited to us.

This is not to suggest that the dating pool is a rigid hierarchy of people who are “better” or “worse” than each other, but that we’re all perfectly-flawed individuals who are really good for some people, and really bad for others.

Example: I don’t think George Clooney is “better” than me. Though is he a better fit for his new wife? Probably. (Though in my defence, Amal has never met me…)

This is not me being arrogant. I truly believe that I would be a better match for a lot of women than George Clooney. And I think, once they got to know both me and George, many women would agree, even if, on paper, George has many advantages that I, on paper, don’t.

So why do I bring this up?

A reader sent me an email concerning retroactive jealousy recently that I’ve received, in different forms from different people, many times before.

Nora from the US writes:

Hi Zachary,

I have somewhat of a juvenile question, but please hear me out.

What do you do if your boyfriend’s ex is actually “better” than you – better looking, more successful, highly intelligent, wealthier, etc.?

I know existentially none of us is more important to humanity than the next person.

But let’s say, for example, my partner’s ex was some beautiful model. Empirically speaking, most people would say she was better looking than me.

How could I compete with that? And how could I not be overwhelmed with insecurity about that?


Thanks for your letter, Nora. This isn’t a “juvenile” question. It’s an important question.

If I was a betting man, I would wager a hefty sum that your boyfriend–if he’s like most of us–doesn’t see his ex as “better” than you.

Your partner’s ex might be Jennifer Lawrence or Beyonce or something, but if your partner is in love with you, and is like most men in love, you are the apple of his eye. The sugar in his tea. The Yoko to his John. The… you get the picture.

If you struggle with thoughts of your boyfriend’s ex, remember: most of us are very present-oriented when it comes down to it.

Let’s break this down: even if you don’t fully realize that your memories are all phonies, how much time per day do you spend contemplating your ex-boyfriends? A few minutes a week, maybe?

Or, more likely, do you spend more time thinking about your next cup of coffee, or that report that’s due on Thursday, or how obnoxious the traffic is today, or trying to remember to remember to bring home a pizza for supper, or how cute and sleepy your boyfriend looked in bed this morning, or…

Most of us spend most of our time thinking about the present. (Unless, of course, we’re suffering from retroactive jealousy.) Most of us spend most of our mental energy on the things that are important to us right now–our job, our relationship, our partner, our current triumphs and challenges. Most of us spend most of our time being interested in what’s interesting to us right now.

With only 24 hours in a day (and seven or eight of those hours spent sleeping), most of the time we’re so busy, and focused on what’s going on in the present, that we have neither the time nor the inclination to ruminate on what happened a year, or two, or ten years ago. Your partner is, in all likelihood, no different.

This is to say: your boyfriend is present. Your partner is with you. And your boyfriend’s ex probably isn’t much of a factor in his life anymore.

And, if he’s like most people in relationships, he’s not just “with you”–he’s really into you. Not his ex-girlfriend, not Jennifer Lawrence, not Beyonce. You.

Think about it…

When we’re in love, we feel like our partner is the sexiest person in the universe.

woman worried about her boyfriend's ex

And as our love for our partner grows, so does our attraction, our drawn-ness, our desire for them. Our appreciation of our partner’s unique attributes, character, magnetism, and charm expands at the same rate as our love for them.

I mean that if I’m in love with you, I want you. Why on Earth would I be pining for an ex? I’ve got you, after all. You are what’s exciting. You are what’s real.

What’s more, I have never “downgraded” in my relationships with women. Not once in my life. And I don’t know many men who have.

Sure, I’ve had different partners at different stages of my growth and development, and some were “better” for me than others, but in the end they were each exactly what I needed at that particular moment in my life.

But I don’t need them anymore. I need someone who is right for me right now. That’s who’s “best” for me. That’s always who is the “best” for me.

Let’s break down your questions, Nora.

How could I compete with [my partner’s ex]?

You don’t.

You realize that if your partner is like 99% of men in love, you are the one he’s focused on. You don’t “compete” with his ex because you don’t have to; you are right for him right now, you are what compels him, what moves his soul, and that automatically makes you the “best.”

Your partner doesn’t see you as “not as good” as his ex, and if he does: why on Earth would you waste your energy, your attention, your devotion on someone who doesn’t deserve you? Why would you choose someone who isn’t choosing you deliberately, decisively, definitively?

And how could I not be overwhelmed with insecurity about [my partner’s ex]?

Easy: you focus on competing with yourself, not your partner’s ex.

If there was a class called “Overcoming Insecurity 101,” the main lesson would be this: always be striving to be better than your former self. That’s personal development in a nutshell. (And also one of the main themes in my online course.)

First, identify exactly what you’re insecure about, or what about yourself you’d like to improve.

Second, find a plan, commit to it, and then work on yourself, constantly. There is no other way.

(And, if you find that there’s nothing about yourself you’d like to improve, you must be Jesus or something. Must be nice, but down here on planet earth we all have things about ourselves we’d like to improve.)

Acknowledging and committing to work on your insecurity isn’t about being unduly “hard” on yourself. It’s about aspiring to your best self, always. It’s about improving yourself, for its own sake, of course, but also for the sake of the people you love. Because, if you really care about them, then you know that they deserve a better version of you, too.

When you get serious about competing with yourself, your drive to “compete” with your boyfriend’s ex starts to fade away.

This is because nothing compares to the satisfaction, the thrill, the rush you get from looking in the mirror and realizing that you’re actively “leveling up” your life.

Realizing that you’re a better version of yourself than you were a year, a month, a week ago.

And, even more exciting, realizing that when it comes to self-improvement, the sky truly is the limit. (I hope you’ll pardon the cliche.) There is always another plateau to reach, another way to improve, a better version of you that is right around the corner, if you work hard enough.

In short: work on yourself, compete with yourself, focus on what’s really important, invest the necessary time to overcome retroactive jealousy, and your insecurity regarding your boyfriend’s ex will take care of itself.

Zachary Stockill
Zachary Stockill

Hi! I'm a Canadian author and educator whose work has been featured in BBC News, BBC Radio 4, The Huffington Post, and many other publications. I'm the founder of, the author of Overcoming Retroactive Jealousy and The Overcoming Jealousy Workbook, and the host of Humans in Love podcast.