I’m 35 & My Boyfriend Is 25. Surprisingly, It Works.

Like, "best relationship I've ever had" works.
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If you had told me that, at 35 years of age, I would have a 25-year-old boyfriend who was the most emotionally mature, supportive guy I’d ever have dated, I would have laughed in your face. I was all for dating younger men, but not THAT young.

I definitely wasn’t searching for a younger man. If anything, I was questioning whether I should raise the age limit on my dating apps from 28 to 30. See, I’ve always dated younger, but consistently found that age, well, MATTERED. I repeatedly got my heart broken by guys three, four, five years younger than me, and was getting pretty sick of it, to be honest.

But then, Paul Mescal was in town.

Paul (we’re on first-name terms) for those who didn’t binge Normal People in lockdown, was the hot Irish star of the wildly popular romantic drama series. He was in Sydney to film, as every celebrity seems to be in 2021, and had been spotted in my area many times. Then, I heard rumours he was on the dating apps – and matching with people.

I was hell-bent on finding him, so I Googled his age. TWENTY. FOUR. Yikes. Still, I lowered my limit to 24 and got swiping. I didn’t find a Paul Mescal but I did find a Tom, 25, who was cute, loved dogs, and had the kind of app-banter I loved. 

After a few days, he asked me out. I was surprised – I’m 35. Why would a 25-year-old want to go on a date with me? 

Now, you can probably tell that I write about my love life a lot, and I also have a dating podcast, Jeans and a Nice Top. So I went out with Tom, primarily for “the story”. Whatever happened, dating a guy ten years younger than me would definitely be *a story*.

We went for drinks at a local bar, then ended up at dinner at a cheap Italian spot. Conversation flowed and he made me laugh. It wasn’t the most magical date of all time, but it was pretty special and I knew I’d want to see him again.

Flash-forward seven months and we’re in love. It’s been the easiest relationship I’ve ever been in – we’re yet to have a serious fight, but I also know when we do, Tom won’t freak out and run away like many men I’ve dated have done. He’s supportive and constructive with his advice on everything from complex work stresses to friendship problems. He can handle my relationship anxieties. He makes me laugh, and I can be myself around him. It’s just easy, and I’m the healthiest and happiest I’ve ever been in a relationship.


Surprised? Same. I didn’t expect dating a younger man to work, particularly given our respective ages. Putting it simply, I figured we would be in different stages of life – far too different to be compatible. But, save for a few serious conversations which I’ll detail below, it’s been smooth sailing.

I do think, if you’re venturing into an older woman/younger man relationship, it’s worth having a few chats prior to getting serious, and asking yourselves some questions. Here were ours.

1. Do you both want kids, and if so, when?

By far the most pressing issue for me with this relationship was the Baby Chat. I’m 35, and I’m still not 100% sure I want kids, but I’m leaning towards yes. Because of that, I’m aware that I should be taking the next few years seriously, as the window in which I’ll likely need to start trying for a baby.

When I was 25 I definitely didn’t want kids. But I’m not Tom, and as he said to me when I blurted out that we couldn’t possibly work because why would he want a baby before he’s 30 – “why are you assuming you know what I want?”

In short – don’t preempt your younger partners wants and needs. Just raise it with them, and make sure you’re on the same page. 

2. Do you fit into each other’s social circles?

Another issue some older women with younger men (or younger partners in general) may face is friendship circles. I have a core group of friends and they mean a lot to me, so it therefore means a lot to me that my partner gets along with them. 

You may find that the interests of your respective friendship groups differ. In my case, Tom’s friends enjoy the same stuff my friends do – going to the pub and sometimes having a house party. But if, say, he and his friends were still club rats or big on festivals, that would be fine – as long as I could happily compromise from time to time and enjoy those interests, too.

You don’t need to have friendship circles that could seamlessly merge, but you do have to assess if you can feasibly enjoy time in your partner’s circle, at least sometimes.

3. Are you on the same page?

This is a question for ANY new relationship, but I felt it was particularly pertinent given I was dating a 25-year-old. Basically – do you want something serious? Do they? There are no wrong answers here, but you don’t want to be assuming things are getting serious.

Dating culture in 2021 is very, very complex and there are many relationships without labels or commitments. It’s likely their dating culture is a bit more casual than yours, so it’s worth checking. I know that’s a stereotype and if Tom reads this, he’ll totally yell at me for it because he got super annoyed when I assumed he wanted a casual fling. But hey, you’ve gotta protect yourself! Just check in before you get too invested.

4. Can you get past what people will say?

My GOD, you get some opinions when you date a younger man. They will, too – both Tom and I have been met with raised eyebrows, words of concern and doubt about our relationship. Most people have been open-minded and happy for us, but you have to be prepared for some of your nearest and dearest being… not so happy for you. 

The main concern is that you won’t work, because the age gap is too wide. But that’s really for you to decide. I can imagine there are numerous 25-year-olds I could never date, but Tom and I just… work. 

At the end of the day, it’s your life. If you’re feeling it, go for it.

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