What It's Like Getting Into a First Relationship in Your Late Twenties

"For a long time, I felt like romance was just something that other people did."
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Photo: Bob Foster

Most people get into a relationship as soon as they start feeling even slightly horny. From swapping saliva behind the bike sheds at school with another gangly preteen to thinking that your uni boyfriend Mark is “definitely the one”, the majority of people treat romantic relationships as if they're as important as eating, or sleeping.

I was not one of those people.

In fact, I didn't get into a relationship until I was 31 – which is a few years after most people get married. Instead I went through my teens and 20s without even a hint of romance. Relationships in general felt like a completely foreign concept to me – something for other people, sure, but not for me.


There were probably a few reasons for this. Being gay meant that it took me longer to come to terms with my sexuality than many of the hetero people around me. Instead I remained in the closet, treating work like a significant other and funnelling all my time into extra-curricular activities. By the time I accepted that I was into guys – in my late 20s – relationships were the last thing on my mind. I was more preoccupied with swiping through Grindr, with flings never lasting more than two or three dates.

But while I might have been in the minority (a 2015 Pew Research study says that 35 percent of American teens have been in a romantic relationship), I'm definitely not the only one.

Dylan*, an MBA student from Virginia, didn’t enter his first relationship until he was 26. Like me, he cites being gay as a contributing factor. Heteronormativity is spooned into us from such an early age that it can often take queer people longer to find what they want. “I think in the LGBTQ community, development happens at a different speed for everyone,” he muses. “For the older gay men that came before us, many never felt comfortable until they were 40 or 50.”

Dylan also cites the fact he was a career-focused introvert, meaning that having a boyfriend wasn’t really at the forefront of his mind. “I think it’s a privilege of being a male; we can wait longer since we don’t have to worry about not giving birth.”


Kelly, based in New York, linked up with her first boyfriend at the age of 26. Before that, she says, it was self-confidence issues that held her back. “Anytime anyone ever asked me out in high school, I thought they were joking and I genuinely did not believe it,” she says. “Even in college, I remember the first time I was texting a boy and thinking, ‘Oh my god, this guy likes me.’ It was the first time I thought anybody liked me. After I began to gain confidence, It was only a matter of time.”

Kenny, from Massachusetts, didn’t have a girlfriend until the age of 29. He thinks that his hesitancy was based around his perception of the meaningfulness of romance. “I think that I put a lot of pressure on love to be something very special and a lot of weight on the idea of a first love and the narrative I thought it required,” he explains. “I was also so paralysed and nervous to put myself out there, and whenever I did I felt awkward, vulnerable and uncomfortable in my own skin. So romantically, I kind of kept to myself.”

Getting into your first relationship in your late twenties or older can come with its own unique set of challenges. You've never been properly heartbroken, for one, meaning you might either be too heady or too cautious. Constant communication might also be difficult when you’re so used to being an independent single unit. Fortunately for me, I got with someone who also was experiencing all of this for the first time, and the result was us not only moving in half-speed, but moving in slow motion while on horse tranquilizers. Which worked fine for us.


These challenges are something Kenny can relate to. Once he was in a relationship, it wasn't all light and ease. “It felt like being 16 years old again, it was so nerve-wracking,” he says. For him, instead of slowly easing into the swing of things, he hit the gas. “It was such a step out of my comfort zone, but I think it is a very rewarding step to take. Things were really intense very quickly and there was a lot to process very fast.”

Dylan says a similar thing. “In terms of me and my boyfriend, I noticed I became emotionally invested much quicker,” he says. His partner also had more experience when it came to relationships. “I let things fester for longer,” he says. “I also let things slide by, like even being patronised for feeling a certain way or having not as much experience.”

When it comes to relationships, there's no one-size-fits all way of approaching things. Some people will never get into a relationship. Others might never want to. And “relationships” as a concept look different for everybody – especially if you’re aromantic or asexual. But for those that do, waiting until your older can also be kind of rewarding. “It was thrilling to experience things freshly that I had felt might never happen,” says Kenny. “It makes me feel centred and alive and connects me very deeply to my emotions – both good ones and difficult. It’s tough, but I know it's worth it.”

*Some names have been changed.