I’m a 37-year-old man and I’ve been on Hinge for three years – I’m being left behind

‘Are you genuinely interested in your dates, finding out about them – or more concerned to upsell your own strengths?’ says Kenny (Photo: Milorad Kravic/Getty)

Finding love is a tricky business – and I’m honestly unsure whether technology has made it easier or harder. I understand why you’ve chosen to try to meet a partner online, and in the time-honoured fashion of a senior adman, it sounds like your instinct is to package yourself up to sell on dating apps. While this might work brilliantly for consumer products or services, your lack of success in getting beyond a first date over the past three years suggests it’s not effective when it comes to people.

In my experience, people want to connect with a real person, warts and all, if they’re considering a long-term relationship – and I wonder if you’re understandably so eager to show your positives that you don’t reveal any vulnerabilities? You’ve clearly got a lot in life sorted out, but I wonder whether you’re able to show up as yourself on dates – not as the polished product, but raw and available to grow into relationships? Are you able to let your masks slip and stop any peacocking so you show more than your surface self?

It’s interesting that you’re trying to meet someone on dating apps because you are so time poor. This strategy of convenience is understandable – though so far unsuccessful – but I wonder how you think prospective partners interpret this lack of time in your life? Many people get caught in the trap of equating being busy with being successful. But to a prospective partner, this might signal unavailability.

Might you be giving out signs that you don’t have the time to invest in getting to know a new partner and sustain a serious relationship? Do you actually want to make time in your very full, enjoyable life for a new relationship? Is there a possibility that this is why you received feedback that it seems like you’re looking for something shorter term? Also, do make sure you’re not closing down chance real-life connections – they do still come along.

I’m interested that you say that you desperately want to be ticking off the milestones that your friends are. I wonder how you think this sense of desperation comes across when you’re dating? Also, and more importantly, why do you want to get married, get a mortgage and have children? Would ticking these things off your list make you happy? Or would it ease your feelings of being left behind and overlooked?

At the risk of sounding glib, wanting to embark on a long-term relationship isn’t the same as wanting the same trainers as your friends. Your thirties can feel tough if everyone around you is settling down in unison and starting to build families. In subsequent decades, you’ll find there’s far less pressure as people’s lives follow their individual courses: some have children, some break up, some move away, some dedicate lives to careers. I wonder whether you’ve questioned what you really want from life, evaluated the expectations put on you by society and rebelled against those that don’t apply to your life? Do you know who you are, what makes your heart and soul feel alive? Can you let go of who you no longer need to be? Do you feel a strong need to be like everyone else?

I don’t know whether this applies to you at all, but so many of my clients don’t know their own needs – some don’t know they even have needs – as they’ve always wanted approval and have never had chance to explore how they want to live. Beyond others approval and liking, do you know yourself? It’s hard to bare your soul if you don’t know your own passions.

I once had a client who went on multiple dates. He was never interested in a second date – he didn’t seem to give anyone much of a chance. It was only years later that he was self aware enough to realise that while he was going through the motions, he hadn’t been available at that time because he wasn’t ready to allow himself to be vulnerable or be hurt.

He’d had difficult relationships with his parents and, understandably, wanted to protect himself from the risk of being hurt again. I would recommend that you ask if you’re allowing yourself to be vulnerable or if you’re keeping everything surface level to protect yourself from being hurt? Have you had your heart broken previously, within your family as you were growing up or in a previous relationship? What is your relationship with your parents? Have you considered their relationship with each other and whether you’d like a similar relationship or not? Are you happy to take the risk that your heart might be broken, perhaps not for the first time? This is the risk we all take when we fall in love – and it takes courage to open yourself to the joys of love if you know the sadness of grief.

You mention that your female friends have no idea why you’re single, and you say you’re polite and chatty. Are you genuinely interested in your dates, finding out about them – or more concerned to upsell your own strengths? Are you showing you want to invest time having fun, flirting, getting to know them, having adventures together? Or is it all about clinching the deal of getting them to commit to being with you long term? Are you really there in the present, able to enjoy finding out about someone, connecting and laughing together, or does the experience feel like it’s ticking the dating box?

The other question I’d ask is whether you’re in touch with your masculine side? You’re clearly comfortable in the company of female friends, but I wonder if there’s a side to you that’s more seductive, flirty and passionate – or whether that side of you is suppressed? If so, it might be time to explore it.

Dating is really hard; I don’t know many men or women who find it easy to navigate. Do know that if you want to open yourself up to a serious relationship, there are many others looking for the same. By getting to know yourself better and allowing others to see your vulnerabilities as well as your positives, you’re giving yourself the chance to find and enjoy developing deeper connections that go far beyond a first date.