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I’m a man in my 30s. I want to date women casually but don’t want to hurt anyone

Ask Roe: Even after going on multiple dates, I still feel like I haven’t found the person for me

Dear Roe,

I am a straight man in my 30s and am writing to you for your advice on dating ethics. I was in a long-term relationship for seven years, and I thought that my partner and I were going to get married, however, in the end, as we both wanted different things from life, we broke up. I was devastated by this, and took a long time to recover, going to therapy, and taking time away from romance to instead nurture my relationship with my friends, my family, and myself.

About a year ago, I finally felt ready to start dating again, and so I started using dating apps. I feel very fortunate, as the dating apps seem to work quite well for me, and I have met a lot of smart, charming, lovely women on them. Nevertheless, even after going on multiple dates, I still feel like I haven’t found the person for me. While I would have loved to have spent more time with these really wonderful women, become intimate with them, slept with them, and formed memories with them, because I didn’t want something long-term with any of them I broke every potential relationship off.

I know it’s possible to enjoy short-term relationships. Yet because I am ultimately seeking a long-term relationship, and because, despite clarity of communication, people can still develop contrary hopes and expectations, I always feel that it’s wrong to extend these encounters beyond a few dates for fear of causing any hurt. My friends (both men and women) are constantly trying to assure me that there is no problem with sleeping with someone even if you don’t have serious intentions with them. Yet I know that those very same friends, when they themselves had invested a lot of time and energy in a potential partner, have been devastated when they learned that said partner wasn’t actually interested. I would love to explore the world of dating fully, and to be open to every possibility, but I don’t want to be someone who hurts others. Could you please advise?


You write that you know that some people have been “devastated” when they realised that the person they were dating wasn’t as interested in them as they were. But there’s a difference between being disappointed and sad that a casual relationship didn’t develop further, and feeling betrayed, misled or manipulated. People feeling a range of emotions and developing hopes and having those hopes disappointed is a natural part of dating and of life. Experiencing negative emotions isn’t inherently a bad thing – it’s part of the beauty of the human experience and the process of seeking out love and connection.

Feeling sadness or disappointment isn’t just a part of life and dating: they are emotions that can tell us about ourselves and lead us closer to what we want, if we pay attention. Having a casual fling and building up our hopes before being disappointed when it peters out could tell us that we’re putting people on a pedestal or jumping too far ahead in an attempt to fast-forward through the work of dating in our desire to meet someone.

Getting overly invested in someone beyond what they have offered us could be a sign that we need to work on our self-esteem because we’re ready to accept any good attention. It could tell us that we need to set boundaries for ourselves and move more carefully through connections, focusing on people’s actions instead of our own fantasies.

It could also be a good sign, if we’ve traded in some cynicism or jadedness for the romantic idealism of hope, that we’re healing and are ready to embrace the world again. It could show excitement and priorities that we’ve met someone who has qualities that are really important to us, and moving forward we could remember to look out for those qualities, while also looking for someone who matches our level of commitment and enthusiasm.

Actor Lili Reinhart once gave an interview to former monk Jay Shetty about her experiences of mental health and spirituality, and one quote has always stuck with me. Reinhart said: “If I started out as this celestial being, just energy, and the universe or God or whomever said, ‘Hey, do you want to go to Earth for an incredibly short amount of time, like a blip, and experience every emotion that you could possibly feel as a human? You get to have all these experiences: love, heartache, anxiety, joy, euphoria, whatever. All of it. Do you want to do that?’ Yeah, I do. And so when I am feeling these intense feelings, it’s sort of like a reality check to step outside and say, although this is a very uncomfortable, painful feeling, it’s quite beautiful that I have the capacity to experience it. That is something that I use to ground myself when I am stuck in a feeling of darkness.”

I often think of the heartache and disappointment of dating and love in these terms; they’re part of the exquisitely wrenching, beautiful, occasionally painful experience of being alive; of being someone who cares about others and connects with them.

So I don’t think you should concern yourself with trying to ensure that no one you date ever feels sadness or disappointment through the relationship. But there are two things I do want you to think about. I want you to make sure that you are genuinely being honest and straightforward with those you’re seeing, and that you’re not ever future-faking or indicating to others that you’re more invested than you are, for example, by making plans for the future that you know will never materialise, or taking actions that might easily be construed as being very emotionally invested, such as introducing people to friends and family. If you can stand over all your actions and behaviour and feel comfortable that you’re being honest and not manipulating emotions, then enjoy yourself, and don’t worry about protecting people from experiencing human emotions if it doesn’t work out.

The other thing I want you to consider is whether you are actually open to a long-term relationship and whether you’re giving yourself and others a chance. You seem to be pre-emptively deciding that a lot of these connections won’t work out long term and then cutting off the connection, and I’m wondering if this is due to your investment in finding a long-term relationship, or is it actually a defence mechanism designed to help protect you from getting hurt again?

You were in love and planning a life with somebody. That’s a deep loss, and it would make sense that you would be somewhat fearful of getting invested again. But crafting impossible standards of how an early relationship should feel without giving it the time, investment, intimacy or opportunity required for it to grow seems like a sure-fire way of cutting down potential connections in their tracks.

I wonder if the concern you feel for other people’s feelings and your desire to avoid causing any pain is actually a subconscious desire to avoid pain yourself. This may be something to explore with your therapist.

You’ve been through a lot, and deserve to have help navigating your feelings around your past experience and this new phase of your life. You seem committed to acting with respect and integrity. Just be sure that you’re as open to embracing joy as you are to avoiding heartbreak, and that you’re not building walls that are impossible for others to climb over.