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‘I like a woman but don’t know whether to follow my head, or my gut’

Ask Roe: My gut feeling is that we won’t have a deep connection, but she has some lovely qualities

Dear Roe,

I’m a single male in my mid-30s and over the years “gut feelings” have played a key role in my relationships and dating — each time leading me to end things (without regret). I am as certain as can be that these feelings haven’t been because of any fear of intimacy, but because of the opposite: they stem from a healthy desire to have a deeply nourishing connection with someone on a similar wavelength as me. However, I have just encountered a person (a friend I’ve recently made) who “I”, my conscious/thinking self, would like to ask out on a date. But the more I demonstrate interest, the more my gut has been giving me the same feelings that has led me to end previous relationships. I know it’s because my gut feels the much sought after “deep connection” won’t be possible with this person, but in my mind I’m thinking, she’s got some lovely qualities and I won’t fully know unless we both have the opportunity to explore the deeper parts of ourselves through dating and perhaps beyond. I’ve been left exhausted by the internal conflict and I’d really appreciate your view on whether this is a situation where I should or should not trust my gut.

For someone so focused on feelings, you’re wildly overthinking this. Ask her out.

A date is not marriage, nor a lifelong commitment. A date – in this case, a first date – is spending an hour or two together see how you feel around each other. That’s it. Of course you will get to know a bit about the person, and if you’re looking for a particular relationship structure or if you want to ascertain whether a person shares your values, you can ask about these subjects directly. But a lot of going on a first date is simply gauging whether someone makes you feel comfortable and engaged, and whether you want to go on another date.


You are currently viewing dating as very end-goal specific – and sometimes that can be understandable. Maybe you want to get married in the next few years or have no interest in even causally dating someone that you don’t see a long-term future with. In that case, remain friends with this person, enjoy getting to know them in a platonic way, and keep your romantic attention for someone who feels more closely aligned with what you want long-term.

Relying on your gut could mean relying on what simply feels easy and exciting

However (you knew there was going to be a “however”, right?), for someone who values their “gut feelings” so much, there’s an interesting contradiction at play here. You trust your gut instincts so deeply that you have ended relationships because of them – but you also do have an instinct to ask this woman out. I wonder how you’re differentiating between “gut instinct” and your “thinking” self, and if you are underestimating where they overlap – or if actually, maybe you have them reversed? I ask because you have met this woman and like her enough to want to spend time with her, yet you are intellectualising your way out of that feeling by analysing her, holding her up to the (apparently yet-fulfilled) idea you have in your head of a “deep connection”, and convincing yourself – despite an “internal conflict” – not to ask her out. That doesn’t sound like you are following a gut instinct, that sounds like you are intellectualising, over-analysing and ignoring your embodied and emotional desire to ask her out on the basis of an idealised hypothetical. Are you actually listening to your gut? Or are talking yourself out of opportunities to connect with people?

This idea of a gut feeling is important – and often deeply misunderstood. Studies have shown repeatedly that our “gut” is very useful when it comes to things like safety and comfort, as our body can pick up even tiny signals about a situation or a person that feel unsafe. However, our gut can also be misled. For example, people with an experience of trauma or hyper-vigilance may repeatedly feel that safe situations are dangerous, because their “gut” is over-primed to look for danger. Similarly, people often talk about things like “gut instincts”, “spark”, and “chemistry” when they meet someone new or start dating, but often, people who talk of “chemistry” aren’t actually experiencing excitement but anxiety, insecurity and even stress, which can be triggered by people who are inconsistent, hard to read, or don’t make us feel secure, keeping us in a heightened state.

This heightened state of early dating can be intoxicating, and some people can become hyper-focused on this early “honeymoon period” when the excitement and uncertainty keeps every communication with the other person feeling visceral and intense. They can then lose interest when the relationship settles into something more long-term, serious and stable, believing that the feeling of security is the loss of “sparks”. But as anyone in a happy long-term relationship will tell you, what comes after the honeymoon period isn’t a loss of connection or intimacy, but another, deeper layer of it.

How often have you stayed in a relationship long enough to reach another layer of intimacy, or to work at maintaining intimacy when life becomes routine?

So I’m curious about your gut feelings. Are they embodied? Is it a state of comfort, or a heightened state of “sparks”? Which do you value, which do you turn from, and why? It is interesting to me that you have ended all of your relationships, and I’m curious about how long your relationships usually last and what precipitates the break-ups – is it a loss of the “spark” that initially attracted you? Is it when the relationship begins to feel more serious, stable and less exciting? And importantly, how do you balance your “gut” instincts with the effort, work and commitment required in long-term relationships? Relying on your gut could mean relying on what simply feels easy and exciting – but how often have you stayed in a relationship long enough to reach another layer of intimacy, or to work at maintaining intimacy when life becomes routine? How often have you tried forms of intimacy that fall outside of the version you have in your head?

There is something rigid and slightly arrogant about your assumption that you know, even before going on a single date with someone, that it won’t be possible to deeply connect with them. Ironically, you are shutting down the hopes of a connection before it can even begin. What would it mean to expand your ideas of what intimacy could look like? For example, if you value a lot of emotional intimacy quickly, how are you underestimating the deep connection that comes with respecting boundaries and building up trust over time? If you value intellectual sparring, how could you learn to meet someone on a more embodied or emotional level? And for someone who values having a clear idea of what you want and not even going on one date with someone who might not match up, what could you learn by remaining curious, by being vulnerable, by trying to forge a connection that you aren’t trying to analyse and evaluate from the jump? What could you learn by paying attention to the ways another person views deep connection, and how they choose to build it?

This woman may not turn out to be the love of your life, and that’s fine. But trying something new, choosing not to write someone off, and listening to your desire to go on a date with her will be valuable. Don’t lead her on, take things slowly, and try to stay in the moment. See what you can learn. Pay attention to the times where you would usually disengage, and try to stay present. See what different forms of connection you can forge.

If nothing else, going on a date will end your “internal conflict”, which seems like a pretty good deal. Good luck.