I’m on holiday in Lisbon with the best wingwoman a single girl could ask for and we’re being served champagne by a charming Portuguese waiter. ‘She’s very beautiful,’ the suave, dark-haired man says to my companion, gesturing towards me. ‘I know,’ she smiles, ‘she’s single too.’ I grin through a blush I hope is dimmed by the candlelight.
This was the second holiday on which I’d found myself shamelessly flirting with bar staff and hoteliers at her prompting.
And you might imagine my partner in crime was a best friend or flatmate of my own age.
Instead, it was my 72-year-old mother, Caroline, who was encouraging me to find love, or at least a little holiday romance.
I’d begun to see the potential when we arrived in Amsterdam for a city break earlier this year. Knowing we’d be out all day exploring, I’d booked to stay at the Generator, which is actually more like a hip hostel than a hotel.
At 35, most of the patrons, milling about reception with their ratty backpacks, were over a decade younger than me.
‘Oh my God, I feel old,’ I told Mum, apologising for booking somewhere so unusual. She looked at me like I was mad. ‘This is going to be so fun!’ she trilled.
My mother is not your average 72-year-old by any stretch – last year, she walked 100km of the Camino de Santiago walking trail in Spain and is in far better shape than I am – but the atmosphere of the place buzzed through her in a way I’d not expected.
Lucy Holden says her 72-year-old mother, Caroline, encouraged her to find an ‘exciting’ holiday romance to boost her confidence after being single for a year
It was March but warm, and people were sitting all over the streets enjoying the sunshine with a Dutch beer, students gossiping and young couples hand in hand.
It seemed to throw her back to her own single days, decades before, and she started not only pointing out eligible-looking men in bars, but making a beeline for them, too.
‘I’m here with my daughter,’ she’d say, bringing them over to say hello.
Her targets seemed utterly disarmed by this sunny approach, and as a pick-up line it worked precisely because it wasn’t a pick-up line at all – at least not for herself.
I was charmed from the start, too. By now I’d been single for a year after a painful break-up and knew Mum was still cross with my ex.
‘I bought the b*****d a Carhartt shirt for Christmas… and £150 shoes,’ she said.
She was determined I should find a man worthy of me – and perhaps a few more besides to boost my confidence again – and I was happy to let her help.
She was 34 when she met my father (they’ve now been together for 37 years) so I think my age was also an unconscious prompt for her matchmaking.
Back at home, Mum would go on my Tinder profile and swipe right on fairly boring types I’d never go for. But in Europe, she seemed to realise I needed something different. Returning from the loo to find me flirting with a man at the next table, she’d simply ask how ‘exciting’ he was.
It was in Paris that her excellent French language skills paid off.
At a coffee shop opposite Notre Dame, she struck up a conversation with our waiter and I felt the chatter turn to me halfway through.
‘He asks if you’d like to have dinner later?’ she translated. But we had plans.
‘Go!’ she said.
She apparently didn’t mind. The idea I’d not spend time with her in favour of a date with a stranger seemed too disloyal though.
I took his number but didn’t text – still, I couldn’t get over how easy it had been for her to get me a date.
Did they feel they couldn’t say no to me because they didn’t want to say no to her?
She’d also leave the hotel earlier than me in the mornings and walk the streets for several hours in case I wanted to see a man I had met, for example, the previous evening.
It was hard to stage an assignation in a hostel – the beds were single for a start and I wasn’t about to stay out all night – but she breathed the possibility into the mother-as-wingwoman idea.
Not in the pushy way you see mothers in Jane Austen novels trying to secure a dowry. There was nothing exasperating, or exasperated, in this – I felt no pressure, and found the whole thing immensely amusing.
She was an amusing and easygoing wingwoman who was always up for possibility – not the pushy kind that you see in Jane Austen novels, Lucy writes
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On the follow-up work trip to Lisbon two months later, we were staying at a beautiful five-star palace and even had our own driver, Gabriel, which stirred a quick, mutual attraction. He was tall with clear blue smiling eyes and impeccable manners.
This beautiful man and I would text initially about pick-up times and destinations.
But soon, the lightly flirtatious messages included the kind of pick-up that didn’t require his Mercedes. The fact Gabriel seemed to love my mother as much as he liked me brought a new side to romance. It felt like a respectful, old-fashioned style of courtship, even if Gabriel and I, sending each other longing looks in the rear-view mirror, were quite keen to introduce some of the more modern elements of dating.
‘It’s been so good for me to spend time with you and your mother, and see how much you love each other,’ he messaged.
‘She goes walking in the mornings,’ I shot back.
‘I’ll be there tomorrow at 10am,’ he replied with a heart emoji.
And it was perfect – this fast-formed affection in our hotel suite.
We were having coffee outside the hotel later when Mum returned from her walk and he got up to kiss her on both cheeks. She just looked between us and told me I was ‘a minx’.
‘Thanks to you,’ I smiled.
I meant it too. It was thanks to her that I was even open to the possibility of romance.
I felt very lucky during our trips to have a mother so up for travelling and fun and possibility. I understood that, more deeply, she thought I’d found everything I’d wanted from life but love.
And when I do find love – proper love, not just the distraction of a holiday fling – she’ll be the first to know.



