Dear Roe,
I’m a heterosexual man in my mid-20s who has recently finished college. I have been single for six years after breaking up with my only ever girlfriend. I have enjoyed my last year of college far more than previous years. I finally made some meaningful friendships, many of which were with women. Other than my girlfriend, I never had even a minor friendship with a female. I have come to realise that I enjoy women’s company more than men’s. I spent most of my life either struggling or not wanting to form deep friendships and so spent a lot time alone, which I generally liked. Since my break-up I also spent a lot of time wanting to be single forever; I wanted more freedom financially and with my time, and I have seen my parents struggle with their marriage. I also had a fear of engaging in penetrative sex (I am still a virgin) even though I have had plenty of sexual thoughts like most males in their teens/20s. I am not sure if I am over this fear, though slowly it is getting weaker. Since my break-up I have not gone on a date or had any intimate contact with anyone. I have become more open to the idea over the past few months of some day getting a girlfriend, or at least dating casually to see what I like/dislike. I don’t want to go looking for my life partner yet (if I ever do) but instead just want to have fun with women and not get too serious – sexually of course but also things like going out for dinner, outdoor activities, travelling, going to concerts and events together and so on. How can I start going about this plan?
There’s a piece by Anaïs Nin about moments of transition – when we are no longer quite who we were, but not yet comfortable with who we are becoming. It speaks to the tension between safety and growth, the fear of change, and the quiet pressure of our own potential. She writes, “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” That’s where you are now. Your day has come.
Since your break-up, since witnessing your parents’ struggles, you have shut parts of yourself down to keep you safe – the parts that long for connection, romance, the vulnerable parts of you that you didn’t want anyone else to have access to. It has resulted in some black-or-white ideas, and a fear here that opening up a little will result in everything crashing in; that if you allow yourself to want, you will lose control. To keep yourself safe, you’ve created rigid identities and absolute conclusions: “I enjoy being alone, so I don’t need friends.” “I was hurt once, so I’ll be single forever.” “I’m not ready for sex, so I won’t pursue intimacy at all.”
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It makes sense that you wanted to protect yourself. But it’s important to remember that these are not truths; they are strategies. Strategies designed to keep you safe. But remember: they are not you. Strategies are walls, not identity. And what you’re noticing now is that the walls are shifting. And it might feel scary, but it’s wonderful.
[ ‘I’ve realised I’m attracted to women – but my friends are reacting weirdly’Opens in new window ]
You’re already experiencing the benefits of being more open to the world, through your enjoyable last year of college, your new friendships, your new connections with women that have shown you that being close to people can feel enriching and energising, not draining. You have realised the importance of connections where you feel safe and accepted. You have realised you like depth and getting to know other people, and you have met people who bring put parts of you that you like about yourself. This is your bud loosening.
So your plan – to date casually, to explore connection, to learn who you are through shared experiences and intimacy without trying to leap straight into a life partnership – is not only reasonable, it is perfect and appropriate for where you are right now.
But just as a word of warning: don’t turn that into a rigid rule or an identity either. Don’t tell yourself that you’re only going to date casually, or that you have to avoid anything serious, or that you do or don’t have to have sex. Don’t try to pre-emptively decide who you will become, or what kind of connections you will accept, or what script you have to stick to.
What if, instead, you decided to just enter the world with curiosity – about people, experiences, connections and, most importantly, yourself? What if you remained open to learning about what makes you feel good and connected and interested and appreciated and seen? What if you remained curious about where your boundaries are protecting you and where they are holding you back? You might be surprised by what you discover.
You might date someone casually and realise you enjoy that freedom, or it might make you feel a little anxious, or you might notice your heart opening in ways you didn’t expect. You might realise that dating a lot is a great way to explore connection and learn about yourself without feeling tied down, or you may realise that relationships feel more fulfilling, or one may lead to the other, or you may go through phases. It’s all possible, so don’t limit yourself by pre-emptively picking one path to walk. Your only task now is to show up to your life as it is happening.
[ Should I tell my friend of the rumours about his girlfriend?Opens in new window ]
Begin in the kinds of environments where you already feel some ease – places where conversation flows naturally and where there is room for warmth and curiosity. When you feel drawn to someone, you don’t need to perform or impress; you can simply say, “I’ve really enjoyed talking to you. Would you like to get a coffee some time?” That is enough. Try the apps, filling out your profile with things you enjoy and experiences you’d like to have. Be respectful, ask questions. See what happens.
And remember: this isn’t only about dating. It’s about building a life. Let the life you want to live lead your social world, not the other way around. Seek out experiences you’re excited by – music, travel, hikes, exhibitions, restaurants – and invite others into them. Even if the connection doesn’t become a lifelong friendship or great romance, you are still building your life outward from joy and curiosity, rather than from fear or avoidance. And that means every experience will be worthwhile.
If intimacy does begin to unfold – emotional or physical – you are allowed to go slowly. You don’t need to rush or avoid. You can say, simply, “I like taking my time”.
It may also help to have support as you explore this new openness. A therapist could help you understand how your past shapes your present, to trust your own feelings and to discern which fears are trying to protect you and which are simply holding you back.
But embrace this phase, of allowing, of curiosity, of exploration. Pay attention to all the world has to offer, and what you have to offer the world.
There is no rush. You are not late. You are not behind. You are unfolding. It will be beautiful.
