I’m a lawyer in my late 30s and at the point now where I’ve got my s*** together. I earn a good salary and own my flat in east London, but I really want to meet someone – all my friends are coupled up and I often feel quite lonely.

A couple of months ago, I started dating someone really great. We had an intense connection and I definitely saw a future with her. I wanted to take things to the next level and show her how I felt about her so I surprised her with a reservation at a fancy restaurant she’d mentioned a few times. We had an incredible date, but it all fell apart at the end.

When it came to paying, the bill came to £320 with the wine pairing. I suggested we go halves – as we always have done – and ever since then she’s been cold with me. Now she’s sent me a message saying that it’s been great but she doesn’t see a future with me and she’d love to be friends. I am so confused.

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I read your message and it reminds me of how hard dating is – even if you do everything absolutely “right”, there might not be that magic click. And what is right for one person isn’t for another, anyway. 

With this “friendzoning”, my suggestion to you is to put yourself in the shoes of your date. It sounds as if you put real thought into the restaurant reservation by choosing somewhere she’s mentioned a few times; I imagine she was touched by your planning to create a memorable surprise. No wonder you had an incredible date, and I don’t doubt that you both felt this.

Then comes the bill and you suggest you go halves, just as you’ve always done. I wonder how that felt for her. It was a surprise dinner so she might not have budgeted for an expensive meal this month; she might have to save for fancy restaurants whether she’s on a similar salary to you or not with high rents, mortgages and living costs swallowing such a large part of people’s income.

So it’s possible that what was meant as a hugely thoughtful gesture on your part inadvertently pushed her into the red – and might have meant she had to cancel other plans she’d arranged before the next pay day comes around. Few people would say anything in a restaurant at the time, but she might have felt a little disgruntled that this night out cost her more than she could afford. 

Even if it was comfortable for her to pay, I wonder if she felt like she’d come crashing down to Earth. She’d perhaps been thinking this was a romantic gesture – and I can see how through your eyes it was – but asking to split the bill when you’d presented her with a surprise night out might have felt transactional and a tone clash from the date that had come before.

Not because she doesn’t believe in paying her way – it sounds as if she’s been very happy with this and she’s not out for a free meal ticket – but the nature of taking her out might, to her, have implied that it was a gift and you were footing the bill. Similarly, if she’d presented you with surprise tickets for a show, she might have seen that as a gift, rather than presumed that you’d reimburse her.

Love isn’t transactional, and not only is dating complicated, but money and generosity often is too. I suspect this isn’t simply about the meal, but echoes your date’s attitudes towards money when she was growing up. 

It’s possible that generosity is a core value for her and was important in her upbringing. You might value fairness and justice more, which no doubt makes you an excellent lawyer. If you see dating as finding a shoe that fits, then a clash in core values can lead to blisters throughout a marriage. If this is the case, you might find that finding someone who you have a similar connection with but who also shares your core values might lead to a natural understanding of each other better. 

It might be that your family structures are different and there was a different emphasis on sharing and fairness when growing up; sometimes even sibling order can have an effect – for example, I’m the eldest sibling in my family and sharing was very much expected of me in childhood. This doesn’t make me more generous-hearted, it’s simply second nature.

Or it might be that your date has told herself that your decision to split the bill after this surprise meal is pushing her away, rather than a move to become closer and take things to the next level. If she feels pushed away, it’s unsurprising that she in return seems cold over messages and has made it clear she sees this as a friendship.

But neither of us know what she felt unless you ask her – and I would recommend this is what you do. There’s still a connection between you and having an open conversation about how she felt when you suggested splitting the bill will give you an insight into her, and might also help you deepen your relationship.

You can honestly explain why you chose to suggest splitting the bill, too. If it’s true, you can tell her you regret rushing to make that suggestion. This gives you both an opportunity to explore issues around money, families and values with an open heart. Whether you rekindle the relationship or not, such a conversation would surely be invaluable for yourself – and potential future relationships. 

It’s honest of you to say you feel lonely. It sounds as if you’re very high achieving in your life, but lacking the vulnerable love that you hope to find. Even if this woman is no longer interested, this experience gives you a chance to reflect on how you would want to live on a day-to-day basis in a long term relationship. How do you see your future? What would daily life look like? Did your parents split money and would you like to do the same, or something different? You might never have thought about these things, but considering the values that are most important to you and the future lifestyle you hope to lead is helpful in meeting a partner. 

I’d recommend considering whether you – like many people – rely on facts and figures, patterns and habits to give you a sense of safety, structure and even control when navigating the world. In order to grow beyond what you’ve known in the past, you will need to be vulnerable: that’s where you will find, in time, the love that you long for. 

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Kenny Mammarella-D’Cruz