How I turned my casual relationship into something more

Couple having coffee on a date talking and smile together.
A couple having coffee on a date. (PHOTO: Getty Images)

Welcome to A Millennial's Dating Diary series, where we explore real-life interactions and the hurdles of dating in Southeast Asia. The series will feature the dating stories and misadventures of Arika – a 26-year-old, straight female marketing manager with a penchant for over drinking — and fellow millennials.

On a recent lunch date with a girlfriend of mine, I was asked: “How did you turn your casual relationship with *Mark into something serious?”

Now, this isn’t the first time I’ve been asked this.

Pretty much all my girlfriends, who have tried casual dating, struggle with talking to the one they like about two things — the status of their relationship and how to take it to the next level.

In all honesty, even I’ve struggled with it. When I first started dating in my early twenties, I was almost always too afraid to have ‘the talk’ out of fear that they would leave me if what we wanted didn’t align.

Now that I’m in my late twenties, my attitude towards asking for what I want has changed slightly — in part because of how jaded I’ve become but, that’s a story for another day.

So how exactly did I turn my casual fling into something more serious?

  • Communicate better

Whether it’s asking for what you want, being honest about your feelings, or even just being open to know about what he’s been up to, it’s important to keep communication lines clear and open between the both of you.

Don’t quite know what to be honest about? For starters, if you’ve both agreed to date casually for a little while, you need to discuss STDs, STIs, and the like.

When Mark and I started dating, we both talked about still seeing other people. We both knew when the other was going on dates (sort of), and we established from the start that we were going to be extremely honest with each other — even if it could potentially hurt. For example, in the past, whenever I asked Mark if he had gone on a date the night before and slept with the girl, he would tell me if he did (most of the time it was a yes), and while I would get jealous, I also appreciated the honesty.

From this experience, I knew that if we were to become a couple in the future, Mark would always be honest with me.

A couple enjoying drinks at the bar. (PHOTO: Getty Images)
A couple enjoying drinks at the bar. (PHOTO: Getty Images)
  • Play the long game

Remember, you’re in it for the long haul, and when it comes to trying to win someone over, it’s a process that will take some work.

Once you’ve decided you want to take things to the next level, you’re going to have to really commit to doing two things: getting to know this person on a deeper level and opening yourself up to them.

Every once in a while, make it a point to do something outside of the bedroom, talk to them about things outside of sex, and most importantly, be yourself. Ultimately, feelings need to grow organically between the two of you, and these things take time.

  • Get to know them better

One of the best ways to connect with people is to let them talk.

Let them talk about themselves, give them a safe space to open up to you, and make them feel like you genuinely care about what they have to say.

This is especially important when you’re trying to turn something casual into something a little more serious. If you’re already dating casually, chances are, you know the shallow details about them.

You know what they do for work, which countries they’ve been to pre-COVID, and which countries they wanna see when we’re finally allowed to travel again. While this is all great, let’s be real, these questions are LAME.

Think about it, what kind of questions do you want to be asked if you want someone to get to really know you?

Want to get to know them better? Ask them what their friends might describe them, what they were like in school, or what they wanted to be growing up. If your date is worth their salt (which they should be if they want to be dating you), they’ll likely give you a backstory about themselves. From there on out, it’s up to you to start a conversation about it and earnestly listen to what they have to say.

multiethnic group of friends sitting on a table in a bar restaurant eating a muffin making faces. diverse people celerating sweet breakfast together enjoying happy holidays. lifestyle and joy concept
Friends catching up over lunch. (PHOTO: Getty Images)
  • Test the waters sometimes

If you’ve established that you like each other and want to take things up a notch, why not let them meet your friends through something super casual like a bike ride or dinner?

When I first introduced Mark to my best friend, Natalie, it was spontaneous. We were already out for drinks, and I asked Natalie if she’d like to come along just to see what Mark was like.

Just be sure to ask your date if they’re OK with the idea. If you both decide to meet friends, don’t put any expectations on whether your friends will like them.

Once, my ex-boyfriend tried giving me a ‘pep talk’ before meeting his friends because he was so worried they wouldn’t like me. The whole experience was unnerving.

  • Be honest with yourself

When I started getting unbelievably jealous about the other girls Mark was seeing, I knew then that I had developed feelings for him and that continuing casually wasn’t sustainable. Still, it took me a while to properly realise my feelings and tell him about them. So, be patient and kind with yourself.

While I can’t guarantee that all of these things will turn your casual relationship into something more, these were some of the things I did — most of them subconsciously — that I think could have possibly led to my relationship going serious.

Yahoo Dating
Yahoo Dating