Can’t get over girlfriend’s past? You are far from being alone.

Today’s letter comes from an American named Ron who can’t get over girlfriend’s past.

It raises several important, and widely resonant issues for sufferers of retroactive jealousy, and sexual jealousy in general.

Ron writes:

Hi Zachary,

I can’t get over my girlfriend’s past. My gf has been with a lot more people than I have. I’m jealous of her, jealous that I haven’t been with as many people as her. I’m jealous that I haven’t experienced a “wide variety” of people.

I’ve only been with two people and that includes her. Basically, I’m embarrassed and disappointed that I didn’t have the “college experience”. During my four years in college I didn’t sleep with one individual. And society suggests that the “norm,” is for college to be that time where you “get it out of your system.” You go on dates, you experience people in the bedroom, so on and so on.

Now I’ve been dating my partner for nearly a year. I don’t know what the future holds. I’m in no position to get engaged, but what if she’s “the one?” I’m very much in love with her. But, now I fear, that if she is the one, I haven’t lived enough, I haven’t experienced enough.

Basically, what it boils down to is that I’m jealous she got to be with other people in college. And I didn’t, and might never get that opportunity again, because what if she is “the one?” What if I can’t get over my girlfriend’s past… ever?

Any advice?



Thanks for writing, Ron. I’m going to tackle each of the issues you raise one by one.

My girlfriend has been with a lot more people than I have. I’m jealous of her.

If you read my guidebook, or took my online course, you’ll know that I like to talk about jealousy and victimhood.

Often, as sufferers of retroactive jealousy, we hold some kind of resentment toward our partner for having the experiences they did; for couples with, shall we say, “imbalanced” sexual histories, like Ron and his partner, this can mean resentment toward our partner—either conscious, or unconscious—for having more sexual experience than we.

Let me share a not-so-secret secret: it isn’t hard to find sex.

Any woman, and most of the men reading this, can walk out of their home right now, find a crowded public place, and find a lover, if just for a night (or morning, or afternoon, as the case may be).

And with “hookup apps” such as Tinder, nowadays you don’t even have to leave the house; all you need is a smartphone. Now, this is less true in some of the more socially conservative regions of the world, but still: in the 21st century, it’s easy to hook up.

Can’t get over girlfriend’s past? Think more experience might help?

Remember that you are not a victim. You have a choice:

You can have more sexual experience right now, today, if you so choose.

If you can’t get over your girlfriend’s past, you might think that more experience will help you. And you absolutely can have more sex, and more sexual partners, if you so choose.

You probably already realize this, but I think it’s important to remind you of your power. Often, we resent ourselves and others because we feel powerless—like circumstances are “beyond our control,” that we have no agency, that other people have all the power. This is simply not true. We can be, choose, and do just about anything we want.

So, first off, acknowledge your power.

Realize that you’re not “stuck” in an undesirable situation. Decide what is more important to you—remaining monogamous with your partner, or finding new partners—and choose it deliberately, decisively.

If you decide that, for now at least, your partner is the only woman you want to love, celebrate her, celebrate her beauty and spirit, love her without reservation. Monogamy, even if only temporary monogamy, can be a wonderful, life-affirming, deeply inspiring and exciting choice. The important thing is to make the choice consciously. You have that power.

Moving on:

I’ve only been with two people and that includes her. Basically, I’m embarrassed and disappointed that I didn’t have the “college experience.” During my four years in college I didn’t sleep with one individual. And society suggests that the “norm,” is for college to be the time where you “get it out of your system.” You go on dates, you experience people in the bedroom, so on and so on.

I found the phrase “the college experience” interesting. I know exactly what you’re referring to, and you elucidate the idea with great clarity, but I find the term misleading.

john belushi can't get over girlfriend's past

I’ve always been a bit of a social butterfly.

Since middle school, I’ve always socialized among varied friend groups. The music kids, the jocks, “cool” kids, I have friends who fit just about any student archetype you can imagine. And guess what? Their “college experiences” vary widely.

Some people find a partner in first year and stay with them for the next four, others have a few unsatisfying one night stands and decide it’s not for them, others are so focused on their studies they remain celibate, others lose themselves in casual sex right up until they graduate, and some people go through distinct “phases” involving a hookup (or two, or three, or…), and then a relationship, then another hookup, then a friend with benefits, then a relationship, whatever.

Some men experience retroactive jealousy, and can’t get over their girlfriend’s past, in their first relationship–and stay celibate for years.

My point is that everyone has a different “college experience,” and yours was not necessarily out of the ordinary.

(Recent research even suggests that our generation is having less sex than our parents did, illustrating the myth of the “college experience” still further.)

Now, you might regret missing out on “college sex,” and I understand that entirely.

And unless your name is Marty or Doc Brown, you can’t go back in time, but again, you have a choice. Judging by your letter I assume that you’re still young (20’s or 30’s), and thus you still have more than enough time to explore new relationships and sexual partners.

Once again, you have a choice.

Now, your girlfriend made a different choice than you did during college, and I can completely understand why that might sting a little, or be a little embarrassing. And if you genuinely have a moral incompatibility, if you genuinely can’t get over girlfriend’s past, I understand.

But remember that your girlfriend isn’t necessarily more sexually or romantically “enlightened” than you are.

More sexual partners does not always equal deeper inner knowledge or more sexual experience in general. Let’s say Bill has had sex with one woman 100 times, and his friend Ted has had sex with seven different women, one time each.

Who has more sexual experience?


Now, I’ve been dating my girlfriend for nearly a year. I don’t know what the future holds. I’m in no position to get engaged, but what if she’s the “one?” I’m very much in love with her, but now I fear, that if she is the one, I haven’t lived enough, I haven’t experienced enough.

Aha, now we’re getting somewhere. “What if I can’t get over girlfriend’s past, and what if she’s the One?” (Capitalization mine.)

The myth of the “One” first impacts us as small children, watching Disney movies and witnessing heroic male archetypes such as Simba or Aladdin find their “Ones” with great drama and fanfare.

Think about it: for our immature, developing infant minds, these enormously captivating stories usually represent our earliest exposure to the idea of romantic love.

It’s little wonder that some of us are still looking for our own Jasmine, even decades later.

Popular media reenforces this notion of the “One” as we age, in magazines, romantic comedies, TV dramas, etc. Every summer, our Facebook and Instagram feeds are plastered with wedding photos featuring captions with couples pledging their endless love for each other. We might even have parents who seem to have found their “Ones” when they found each other. It seems, everywhere we turn, just about everyone has found their “One.”

But here’s the thing:

I don’t think anyone has one “One.”

Some of us find people who are extremely well-suited to us, and that’s a beautiful and rare thing. But are they the only potential “One” for us?

There are seven billion human beings on the planet, roughly three and a half billion of them women. Excluding young girls, married women, lesbians, and otherwise ineligible candidates, that leaves you with around a billion different options. Have you ever received the following counsel from a friend in the wake of a breakup: “Ah don’t worry pal, there’s plenty of fish in the sea?” It’s a tired, clunky old analogy, but it’s true.

Right now, as of this moment, there are thousands of potential women who could make you very, very happy, and who would make wonderful life partners.

They may not live on your street, or in your small town, but they are out there.

I’ve been fortunate to live in several different countries on several continents around the world, and explore relationships with different women in those countries. And I learned something important—I can be drawn to many different types of women. And different types of women can make me equally happy.

In certain phases of life we might think we have a certain “type,” or that we’ve found our “ideal” partner, but we’d be wrong.

The “perfect” woman or man doesn’t exist.

There are simply some people who are better suited to us than others, and we make the best choices we can based on their merits, chemistry, etc. Hopefully, we change as we age–we grow and evolve as people–and thus, our “taste,” our idea of the “perfect” woman will also change.

So my advice would be to try to let go of the “One” fallacy. I’m still a romantic at heart, so I understand its appeal, but I also believe that it isn’t a healthy perspective for relationships.

Now, if we choose a partner in any sense—whether for one night, or for a lifetime—we should choose them deliberately, decisively. We might even offer our devotion to them for a lifetime.

can't get over girlfriend's past

But every relationship ends, whether it’s a result of breakup or death. 

And in such a sad event, there is absolutely another potential partner who can and will make us very happy. (Not to mention the fact that when we deem our partner “the One” we often become needy, jealous, possessive, insecure, sometimes even desperate to hang onto them. Pretty unsexy, counter-productive stuff.)

Let me be clear: I am not suggesting that we proceed in our relationships with a sense of cool detachedness as a result of knowing that there are other potential “Ones” out there for us. Absolutely not.

We should just remember that everything in life is impermanent.

Feelings change, relationships change, breakups happen, and death happens. Every relationship ends, one way or another. (More hastily if we genuinely can’t get over girlfriend’s past.) And as a result of this knowledge, we should love and appreciate our partners right now—today—all the more, as we may not have the opportunity tomorrow.

Going back to the issue of your girlfriend having more sexual experience, and whether or not you have “experienced enough,” this I cannot answer for you. That’s your responsibility. What I can do is remind you of the power of choice, encourage you to indulge in a bit of good old fashioned introspection, and trust your gut.

If you come to the conclusion that you genuinely can’t get over girlfriend’s past, it might be time to move on.

Moreover, if you’re questioning your commitment to the relationship over and over, and constantly thinking about other women, it might be a good indication it’s time to leave.

If the question of your inexperience continues to nag at you, it might be worth going out and pursuing those new experiences with other women. It might be a good idea to talk the situation over with a trusted, older male friend.

Here’s a very good video from the School of Life on the question of breaking up:

I won’t lie to you: I think it’s important for a man to feel capable of meeting women, seducing them, being a good conversationalist, and knowing that he will always have “options” should he ever find himself single.

Increasing your sexual confidence can increase your confidence in other spheres of life, and make you feel like a stronger, more self-assured person.

Can’t get over girlfriend’s past, and lacking experience with women?

There are ways to become more confident interacting with women, and expanding your perspective on sex and relationships without leaving your partner (making female friends is the easiest way). However, it’s easier to do this while single to say the least.

In keeping with this article’s tradition of corny old aphorisms, remember that the grass is indeed often greener on the other side.

If you choose to pursue other women, you’ll almost certainly have moments of missing your partner, and regretting breaking up with her. It will probably hurt. And if you stay with your partner for the rest of your life, you’ll occasionally think about missing out on other women, and have moments of regret. It will probably hurt.

Pain is inescapable, moments of confusion are inescapable. When you can’t get over girlfriend’s past, it might feel like pain and suffering is inescapable.

But suffering is escapable—it’s about shifting our perspective, making deliberate choices, and then accepting those choices, even when they hurt.

Nobody has “love” all figured out.

I certainly don’t. I simply try to make the best decisions I can through introspection, reading and research, talking with friends, meditation. And then, I try to accept those choices as the best decisions I could make with what I knew at the time. Thankfully, we humans have a remarkable gift for rationalizing our choices after the fact, so it’s rare that I feel real “regret” when it comes to my romantic decisions.

Many readers—particularly males—write to me with questions aimed at minimizing the potential for future regret, asking me to play Nostradamus for them. This is difficult, usually impossible.

We, humans, make a million decisions a day, and if recent years have taught us anything, it’s that the future is damned near impossible to predict, whether it’s the results of an election, the future of the world, or our own love lives.

I’m simply doing the best I can with what I know at the time. And that’s all you can do, too.

Hope this helps, Ron.

Can’t get over girlfriend’s past?

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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.