How to Make Dating Fun From a Girl Who Went on a Date a Week for a Year

Practice makes perfect.


Welcome back to “Six and the City,” a dating column where I share my experiences dating in New York City. If you’re new here, here’s the short version: I was chronically single for seven years, avoiding dating until about a year ago when a date called me out on my avoidance. My best friend and I committed to going on weekly dates, which we tracked through a spreadsheet. This column is about those dates and everything I learned from my year of dating.

If you read my last article, you know about my “Billys,” or the two guys with the same name that I hooked up with back to back (it was fun, okay?). Now, the reason I bring this up is for that exact reason: the fun of it all. Let me backtrack a little.

Sometimes being single sucks, and the media loves to remind you of it too. The idea that you can’t truly be happy if you don't have a significant other is CONSTANTLY being shoved down our throats. But I am here to tell you that the idea that being single is miserable does not HAVE to be true. Being single is exactly what you make of it. So if you’re focusing on the fact that you have no one to watch movies with on a snowy day or someone to give a cheesy gift on a holiday, yeah, you’re probably going to hate being single.

I started the dating series as a way to get over some of my insecurities and anxiety about dating, but what I didn’t realize going into it was that what I needed was a way to make dating fun. Instead of feeling like dating was a chore I dreaded, like the pile of laundry that never seems to go down, I wanted dating to be something I looked forward to. And if you want this to be the year you stop being the chronically single person always complaining about it, friend, I suggest you do the same. So here’s my advice.

How to make dating fun

Make goals

If you’re goal-oriented, make some dating goals that are specific and achievable. My goal was one date a week, and being able to check off “date” each week on my to-do list WAS fun. If one a week is too much for your schedule, try every other week!

Lean into the data

Speaking of to-do lists, I went a little type-A and also created an Excel sheet of my dates. It started as a way to keep track of my friend and my dates (so we could hold each other accountable/know who the other was talking about), but it quickly proved itself to be a helpful data tool as well. It allowed me to see where I was meeting most of my dates, where dates went better than others (drinks vs. coffee), and what traits I was generally more attracted to.

Get clear on what you want

“Vision board” your ideal date/partner/dating life. It's important to have a general idea of what you want. If you don't know what you want, that's ok too! But keep in mind your intentions as you go through your dating journey.

Involve your friends

Find a friend to date with. Sometimes easier said than done, I know, but dating is SO much more fun when you have someone going through the same thing you are. You can swipe together, go out to matchmaking events together (or even just the bars) or take it a step further like my friend and I did and go on secret double dates. This is where we would schedule our dates for the same place, same time, and have dates across the room from another. This is in part due to safety, but I found that having someone I knew in the room, even if I wasn’t interacting with them, made the date so much less nerve-racking. And it’s fun to have a mid-date check-in in the bathroom with your girl.

Shift your idea of what success looks like

Change your mindset around the idea that bad dates (or even dates that are fine but don’t lead to a second) are a waste of time. Think of it as meeting a new human, getting to hear what makes them happy, and how they like to spend their time on earth. Or maybe you’re like me and love to talk, and what better place to talk about yourself than on a date? If your date is truly awful and boring but you don’t see yourself making an escape any time soon, start making things up. If you’re not getting a good, meaningful, or fun conversation out of your date, you might as well get a good story out of it. Take one of my friends, for example. She went on a date with a guy who confessed to her halfway through the date that he considered himself an “alpha male.” Talk about an immediate ick. But in her mind, since she already knew she wasn’t considering continuing to date him, it was hilarious. A good bit that she could keep up while having another drink to share with the group chat later.

Habit stack

Habit stack your dates by going to new places. Living in New York City means I have an ENDLESS list of restaurants and bars I want to try so I figured a weekly date was a good way to go through that list pretty efficiently.

Talk about it

My final suggestion is to document or vlog your experience. Even if you're not posting it anywhere or only sharing with the group chat, memorializing the experience helps to make it more of a “bit” and less of a chore. I personally do the same with both dating AND cleaning, and it really does help sometimes.

Lastly, remember that nothing is THAT serious. Let go of the expectation that every date has to be the “one” or lead to something serious. Actually, let go of expectations as a whole. He didn’t text you back? Ok onto the next. Do you want to double-text? Go for it. Sent a risky text and now you’re doubting it? Oh well. Let go of the little things. If it won’t matter in 5 days or 5 weeks, it’s definitely not going to matter in 5 years. Dating can be fun if you let it be, so let it.





A self-proclaimed “body neutrality advocate,” Sixtine uses her platform in the hopes of inspiring others to embrace their bodies regardless of their shape or size. She has modeled for notable brands such as Target, Warby Parker, Ulta, SKIMS and Aerie. Born in Brussels, Sixtine and her family moved to Fort Worth, Texas, when she was 3 years old. She moved to New York City at the age of 18 to pursue a career in modeling and attend NYU’s Gallatin School of Individualized Study, where she obtained her B.A. with a concentration in psychology, human rights and politics, with a minor in child and adolescent mental health studies. Sixtine makes her SI Swimsuit debut in the 2023 edition.