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‘I’m about to propose to my girlfriend, but can’t stop thinking about a fling I had’

Ask Roe: The excitement of it still lingers in my mind. How can I overcome this shame?

Dear Roe,

I (mid-30s male) have been in a relationship for the past five years, and I intend to propose to my girlfriend soon. She is beautiful, caring and thoughtful, and I can see a bright and happy future for us together. What fills me with shame, however, is how often my mind flashes back to a girl I had a brief fling with before starting this relationship. Honestly, I was treated terribly during this fling (lots of dishonesty and game-playing) and I called an end to it for my sanity after a few months, but the excitement of it still lingers in my mind. It’s not like I’m going to ever leave my current relationship to go and find this other person (who now lives abroad), but I do wish I had some way of simply removing this memory. How can I overcome this shame?

You’re in luck! There’s some exciting technology that can assist you with this problem! Lacuna Inc, founded by Dr Howard Mierzwiak, provides a revolutionary service. Lacuna will eliminate the memory of anyone you choose from your life, be it a dog, a lover, a deceased loved one, or of course – the popular choice – an ex. The aim of this service, as explained by a Lacuna associate, is “to let people begin again. It’s beautiful. You look at a baby and it’s so fresh, so clean, so free. Adults, they’re like this mess of anger and phobias and sadness, hopelessness. And Howard just makes it go away.”

Sounds fantastic, right? Or fantastical, I should say, as that’s actually the plot of Eternal Sunshine of The Spotless Mind. If you’ve seen the gorgeous 2004 film written by Charlie Kaufman, you’ll know that Jim Carrey’s Joel and his ex-girlfriend Clementine (Kate Winslet) have a bad break-up and decide to erase each other from their memories to help them move on. Except, as it turns out, memories of important relationships aren’t that easy to erase, as memories of love can seep into the very foundation of our being, intertwining with our emotions and ideas of love, affection, conflict, family and the self.


The good news is that you don’t actually need to erase your memories of this person because your memories of her aren’t the problem. The problem lies in how you’re framing the experience of thinking about this ex, and your sense of shame around thinking about her at all. This shame isn’t necessary and isn’t helping you – it’s actually adding a deep emotional charge to the memories, making the very act of thinking about your ex feel tinged with a sense of danger, transgression, betrayal and even excitement, in the adrenaline-filled way that secrets can make us feel. What’s interesting is that the way you’re feeling about the memories you have of your ex sound a lot like how the relationship itself made you feel: exhausted, toxic, destabilised, self-destructive, lacking in honesty and transparency – but also excited, obsessed, maybe a little bit sexy?

You don’t need to never think about your ex, but you need to stop giving these memories so much power. You’re not planning on betraying your partner, you’re not looking to seek out your ex; she no longer lives in your orbit. (I am going to assume, hopefully correctly, that even if she did live in the same country as you that you still would not be seeking her out.) You thinking about her isn’t a betrayal or an infidelity, and framing it as such is adding to the transgression-shame-obsession cycle.

You left your old relationship for a reason, knowing that intensity is no match for respect, trust, honesty, loyalty, clear communication, shared values and a possible future

You’ve been with your girlfriend for five years and are thinking about proposing and making such a big decision, even happily, might naturally bring up some thoughts or memories about previous relationships as you prepare to commit to someone forever. It also is natural that memories of this ex in particular might linger as the relationship was defined by toxicity, drama and game-playing. It sounds like the experience was possibly a constant cycle of intense conflict or insecurity and then passionate reconciliation, and this kind of toxic cycle can feel addictive as every emotion is heightened. The lows feel very low and in contrast, the highs feel intoxicating – even though the highs short-lived, unsustainable, and actually not that great. But compared with the happy, drama-free contentment and even routine of a healthy, long-term relationship, the acute daily intensity of feeling may be lesser now.

But that’s not a bad thing. You left your old relationship for a reason, knowing that intensity is no match for respect, trust, honesty, loyalty, clear communication, shared values and a possible future. You ended your fling because you knew it wasn’t working – and that relationship helped you clarify what you actually want from a partner. You’re viewing this fling as some shameful secret of your past, when the reality is you enjoyed parts of it, were tortured by others, but ultimately it was a relationship that helped you grow and evolve personally, define your values and find your person. If you stop viewing this fling as a clandestine competitor to your current relationship, and see it as part of the journey that found you your future wife, you may start feeling more comfortable about everything.

And if you ever start getting caught up in some overly rose-tinted nostalgia about the excitement of your former fling, remember that it’s easy to romanticise and idealise flings precisely because they’re short. They remain in the obsessive, intense honeymoon phase that’s filled with projection and pheromones and often lacks grounding in reality. You’ve been with your girlfriend for five years, which means you’ve likely settled into a routine, you’ve navigated the mundane details of life together, you’re no longer performing for each other and feel comfortable and settled. With your ex, you never had to discuss chores or schedule visits to each other’s families, you never had to go through the unromantic responsibilities of life together. It remained in the honeymoon stage – but was still, don’t forget, an absolute disaster.

Trust me: endless drama gets boring too, in a very different and far more damaging, exhausting, soul-eroding way

So if you ever start overly romanticising your former fling, imagine what it would be like if you had stayed with that person for five years. What would it be like to marry and even have children with someone who was dishonest and insecure and dramatic and disrespectful and who played games instead of communicating honestly? Imagine what it would be like to navigate the hardships of life with someone who couldn’t be trusted or counted on, what would it be like to go through a divorce and custody battle with someone who, even at their best, enjoyed playing games and manipulating people? I think some of your shame around thinking about your ex comes from the guilt of comparing the excitement of that fling with the steadiness of your current relationship. But trust me: endless drama gets boring too, in a very different and far more damaging, exhausting, soul-eroding way. If you feel your current relationship could do with a bit more excitement, then invest in creating it by planning some new experiences and breaking out of your routine. But don’t confuse conflict and drama with positive excitement, because they’re not the same thing.

You don’t need to shame yourself for thinking about an ex, but you do need to start consciously reframing how you’re thinking about her. I believe that all relationships, no matter how short, can teach us something about ourselves, if only we take the lesson. You learned that you wanted a relationship filled with trust, honesty, respect, care, thoughtfulness and long-lasting love. You made a choice and found it. Your fling got you where you are. That’s not shameful, that’s life and growth and evolution.

Best of luck with the proposal.