‘I’m sleeping with my ex-boyfriend and want him back – but don’t want to scare him off’

Dear Roe,

I’m a 28-year-old woman, and at the beginning of the year, my boyfriend and I broke up. We had been together for two years. He told me that he had slept with a woman he knows through work after a night out. He told me that it only happened once, that he wasn’t in love with her and didn’t want a relationship with her but that he had realised that I was “the type of girl you settle down with” and he wasn’t ready to settle down.

I think I took it quite well, considering, and while I was obviously upset, I understood and appreciated that he had been honest with me, had taken responsibility instead of blaming me or our relationship, and ended the relationship before having a full-blown affair. I was clear that I wanted to be still be friends, and we continued to text each other regularly and meet up for coffee every few weeks.

When lockdown happened, we were talking a lot, and eventually, a couple of months ago, we started sleeping together. I’ve realised that I want to be together again, and I don’t know how to broach this with him without putting pressure on him. How do you have the relationship chat with someone you’ve already had a relationship with?

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When I write this column, I’m very aware when I’m about to tell someone something they don’t want to hear. I usually make this explicit, and assure the letter writer that I’m genuinely not trying to make them feel hurt or angry, but that I’m trying to give them some insight that will protect them or empower them.

Today, I’m going to tell you some hard truths that I hope will protect you and empower you. But this time, I am actively rooting for you to start feeling hurt, and start feeling angry. You need to start feeling something, and you need to stop burying those feelings down under five million layers of shame.

I don’t know who it was who told you that in order to find love, a relationship, a man, you have to be the Cool Girl, but someone did. Someone or some ones or some of the five billion social and cultural messages that are encoded into this world we’re living in told you that getting emotional is something shameful and embarrassing; something only weak women do.

Someone told you that expressing what you want is needy, that setting boundaries is high-maintenance. Someone told you that men need to sow their wild oats and that you should accept this and wait for them to eventually realise that your patience and understanding and lack of neediness marks you as a Cool Girl, the kind of woman you do indeed settle down with.

Any and all of the messy emotions that are swirling around inside you are valid, and you need to stop being ashamed of them

This is why when you found out your boyfriend of two years slept with someone else, your main focus was to make sure you “took it quite well”. Who told you that you needed to take it “well”? And who told you that “well” meant shutting down any of your feelings and instead focusing (not for the first time, I’m guessing) on him? I’m not saying you have to key his car and burn all his belongings in your front garden, but I am wondering why you believe that when you’ve just been betrayed, it is your responsibility to be calm and understanding and make your boyfriend who has just cheated on you and is breaking up with you feel comfortable?

Because he already felt pretty comfortable. Comfortable enough to not feel the need to wait, respectfully end his two-year relationship, and then have his one-night stand. He was comfortable enough to disrespect you and your two-year relationship not because he had fallen in love and was having some serious inner conflict, but because he felt like it; because this woman was right there; because waiting a day longer would have been inconvenient; and because above all else, this man appears to value convenience.

And instead of expressing any completely justifiable pain or anger or betrayal or confusion or exasperation, you were “clear” that you wanted to be friends – immediately. You refused to even contemplate taking any time to grieve this relationship, or be annoyed at him, or to get some headspace, and instead launched into being his Cool Girl Friend, the Coolest Ex-Girlfriend in the world, the Cool Girl With No Feelings Just Texting Her Ex Regularly And Having Coffee and now you’re the Cool Girl Having Casual Sex With Her Ex Like Cool People With No Feelings Do.

Except you do have feelings. You always did. And instead of admitting that to either yourself, or to him, you’re wondering how to broach restarting your relationship without “putting pressure on him”.

Because we all know that your desire for a relationship with a man you were with for two years and have been sleeping with for months could, if you’re not careful, be easily perceived as having feelings, and feelings are utterly terrifying and could crush a man to death unless you public relations the hell out of them, and present yourself as a Cool Girl.

You do not need to be cool.

You loved this man, he hurt you, you still want to be with him – and you are allowed to express all of that. Any and all of the messy emotions that are swirling around inside you are valid, and you need to stop being ashamed of them, need to stop pushing them down in order to present a Cool Girl façade.

Because being the Cool Girl isn’t working.

Your boyfriend cheated on you. And he is, I fear, sleeping with you during a pandemic only because his options are limited and you’re there and not asking anything of him. You are convenient to him. You have always been convenient to him. You have made yourself very convenient for him for over two years, and he is still not offering you the love and respect and relationship you want and deserve. So what have you got to lose by finally, finally expressing what you want, out loud?

Nothing. You will lose nothing. Either this man will tell you that he wants to try again – or he will leave. And if he leaves, you will not have lost anything – because you do not have him.

And what you will have gained, is the rest of your life. A life where you express what you want and what you need and what you feel, and aren’t afraid of that. A life where you know that people love you and respect you not because you shrink yourself down to a convenient empty slate, but because you are messy and complicated and gloriously human. A life where your ability to express your feelings attracts people who express theirs, who are honest about their desires and open about their needs and confident setting boundaries. A life filled with honest, rich, complex, loving relationships – including the relationship you have with yourself.

And you know what that life is? Pretty goddamn cool.