If You Saw Your First Love Again, What Would You Ask Them?

We sent these former sweethearts out for dinner. Here's what happened next.



Tamara, an editor and content producer, 27, and John-Paul, a TV/film production assistant, 30, had an on-again, off-again relationship for two years while at university. Both currently single, they agree their relationship ended because it lacked a certain “intimacy” that they couldn’t entirely explain.


“John-Paul and I had one of those tumultuous on/off relationships you have in your late teens. We had this instant chemistry, really great banter, could talk for hours about anything. It was a great connection and meeting of the minds. But for some reason there was also this tendency for really extreme fights. I guess we were like magnets – attracting and repelling.

“It always felt like there was a third person in our relationship: our friends. It’s like that at uni. I feel like we never managed to have the privacy we wanted because everyone knew our business. He was very social – always had somewhere to be with his mates. I’m more of an introvert and found that hard. “When I saw him again he looked good. Once we got past that slightly awkward half-hug and kiss on the cheek it was fine – we chatted for five hours straight. 

“As the date went on it was hard not to be attracted in the same way.  We change over time but the cues don’t go away – the fact I find him good-looking and charming and interesting was still there. But as the night progressed we started to talk about recent relationships and at that point the night turned more towards supporting each other in our respective dating journeys now, which is fine. It could have gone either way but once we got to that it was like ‘OK, this is more like a good friendship.’ 

“When he walked me home he stood outside  my apartment and asked, ‘Shall we do this again, where do we go from here?’ I said, ‘Yeah, we should catch up.’ And I guess I really meant that. “But I don’t know if I see potential. I think on paper we would work and we’re both single, but I’m not sure we’d revisit the relationship. It’s a bit hard to read him sometimes. He’s a really great guy, but he’s always been an enigma to me.”



“I wasn’t nervous or awkward meeting up with Tamara again. In fact I was shocked at how much we fell back into conversing in exactly the same way. We see eye-to-eye – we’re both fairly neurotic, we both have a great appreciation for [the author] Bret Easton Ellis. We had so many things in common, which makes you realise why you thought it would work at the time. 

“When we were talking about the first time we got together we remembered things very differently: she recalled that someone else was vying for her affections, whichI didn’t remember.

“And I remembered her talking about a movie which she said I should watch and I still haven’t – it’s been on my to-do list for 10 years.

“Tamara and I had that rare experience of knowing when we finished things that we’d really given our relationship our best shot. Even when we were hanging out for this experiment, we had a fun dinner and it almost seemed like a great date. But really we were two people who knew we were just there to explore history and be nostalgic. 

“I still don’t know if I could really define what was missing in our relationship. We just didn’t get to a place where we both thought we’d [be on the same page] on things. Looking back on relationships I’ve had since that really ripped me apart, you can see that it was more one of those ‘young’ relationships where neither of you have a clue what you’re doing.

“I have this theory that there always has to be a diva in a relationship – either the male or the female. And if you have two very like-minded people you can basically get caught in a relationship that doesn’t bring out the best in either of you. Maybe we had the same sort of flaws and views on life that weren’t bringing anything to the table, except the same frustrations.

“We had a great time seeing each other, but it won’t be more than that. I think we’ll hopefully be friends.”

Tamara & John-Paul

Matilde-Rose, business owner, 25, and David, a copywriter, 28, dated for about a year in their late teens. After David broke up with her, Matilde-Rose was devastated. Today, though, she’s married, and David is married with a baby.


“Matilde knew what she wanted from life and I was immediately attracted to her. She was really easy to talk to, and as a socially awkward teenager, that was no small thing!m “Our relationship was great but very intense. I was in love with her, but the feeling of wanting to be in love was bigger. She was my first girlfriend; I fell pretty hard. Eventually I started spending more and more time at Matilde’s house, until I basically lived there. 

“A year in, I knew we weren’t compatible. The day we broke up was horrible. We were in the middle of this busy shopping centre, both in tears. I felt so guilty. When she left I remember falling on my hands and knees and sobbing. It sounds melodramatic, but it felt like a chapter of my life was over – and, of course, I’d just broken Matilde’s heart, the first girl I had loved. 

“Seeing Matilde again was fascinating. When she walked in, my first thought was, ‘Oh wow, she’s an adult!’ But she was still the same Matilde. She’s always been very confident, and you could see that immediately. She didn’t seem to have changed at all. 

“I was surprised at how easily the conversation came – it was like no time had passed. We talked,for two hours straight. There were quite a few things we both looked back on fondly from our relationship. But there were some odd moments, too. We ran into a friend of hers and Matilde had to explain, ‘This is David, he was my first boyfriend. No, it’s all fine, my husband knows we’re meeting!’

“Before we parted ways, we discussed the possibility of meeting up again. Matilde hasn’t met my little son, so I hope that will be the next thing we do together.

“I know that our break-up really came out of the blue for Matilde.  I did wonder if she would bring it up with me but she didn’t. I think it would have been too awkward, even this many years later.

“I guess if she had asked I would have said that I was sorry, and that I was too young to know how to act in the moment. I wish I’d done things differently.”



“David was my first serious boyfriend. He was very charismatic, and just my type: tall, skinny, good-looking. We got along so well – I’m a bit weird and he’s a bit weird!

“Despite what we felt for each other, there was always a sense of disconnect between us. Looking back, we really didn’t have anything in common. Still, the relationship is one I treasure. David was always very caring; he always looked after me.

“I was totally heartbroken when David broke up with me. It came out of nowhere. He sat me down outside the cafe I worked  at, and held my hand and told me he didn’t want to date anymore. It was like something out of a sappy teen movie. Even though I was sad, I remember him being so kind to me, and really taking care of me. That’s the kind of guy he is.

“I didn’t bring up the break-up with David, but we did talk about what came straight after, which gave me some closure. He told me about the different relationships he had after me and I knew that the problem wasn’t me, he just wanted to get out there.

“I didn’t feel an attraction between us, but there was a definite sense of familiarity, of warmth. I don’t harbour any ill will towards David at all. Strangely enough, I noticed a lot of similarities between him and my husband! Maybe it just means I have a type – creative weirdos, I guess.

“Seeing David was a really nice experience. He was a good boyfriend and I’ll look back on our relationship as a nice stage in my life.”

David & Matilde-Rose

Ali, a make-up artist, 30, and Gavin, a production manager, 28, met at church in their early 20s. But when the church disapproved of their love, Ali returned to her hometown without telling Gavin.


“I was 22 when I met Gavin. I was studying at bible college, and did a placement at a regional church three hours from home. I didn’t know anyone, and there was Gavin – he was so funny and friendly and warm. I’m a sucker for a bad Dad joke, and he had them down to a fine art!

“The college didn’t approve of us dating and there were a lot of people working against us. When it all came to a head, I left the church – and the area – to go home to my family. I didn’t handle it very well. But how many young relationships end up with the white picket fence, you know? Deep down, I knew Gavin and I weren’t really compatible. I thought the best thing to do was to cut off from him completely.

“There was a part of me that always thought, ‘I wish I’d handled that differently.’ So when the opportunity came up, I thought, ‘I want to see him.’

“When Gavin and I met up, there was a really nice  sense of nostalgia – like hearing a song you used to listen to in high school. He looked exactly the same as he always did but with a better haircut and better clothes – something I’ll credit his new girlfriend with! I wouldn’t say I felt a sense of attraction, but it was surprising and refreshing to know that we could still connect. Our conversation, even though we hadn’t seen each other in almost 10 years, never felt forced.

“It was good to see Gavin so happy. I wasn’t looking for closure, but I think he was. For me, it was confirmation that I’d made a good decision. There was a reason it ended the way it did, and I’m glad I trusted my gut.”



“At the beginning, we had a great relationship. I hadn’t experienced much and Ali opened my eyes to a lot of things.

“About a year into dating, Ali basically left without telling me. We were technically still together, but neither of us were emotionally intelligent enough to deal with the situation. We got into a big argument on Facebook, which shows you how immature we were! When we met up, we apologised for the words we used.

“I was nervous but excited to see Ali. She looked pretty much exactly the same, just a little older — there wasn’t really any attraction though.

“As we chatted about the break-up I realised how much I’d regretted what I’d said and how I’d behaved. It was a relief to be able to apologise to her after all this time. I’m happy that she’s found a great guy.

“Ali and I got along like a house on fire, we always have. I’m so happy I saw her again, even though it was weird initially. It was good to get some closure and change our ending – now it feels like it’s a good one.”

Gavin & Ali

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