How to Take Yourself on a Date

I’m an introvert in a long-distance relationship, and I work from home. This all means that I spend a lot of time alone. For me, that doesn’t just mean sitting around at home: sometimes it means taking myself out. For as long as I can remember, I’ve enjoyed solo outings – though, as I’m occasionally reminded when someone gives me a weird look, not everyone is as comfortable with the notion of the self-date.

However, if you’re introverted or single or otherwise relegated to frequent solitude, I think it’s imperative to make your alone time not only as frequent as you want but also as special as you want! So here are some of my best tips for taking yourself on a date…

Psych yourself up. It can be hard to drag yourself to a traditional date activity, like dinner or a movie, on your own if you think people are going to judge you for it. So just remind yourself that no one really pays that much attention to strangers in public, and people do this kind of thing all the time. Get hyped for your outing: put it in your calendar, plan it out, make it something you look forward to, just as you might with a “regular” date.

Pick an activity you love, even if other people might not. Some of my favorite solo dates are dinner, going to see a movie, or attending a comedy show. Sometimes the restaurants, movies, or shows I pick are ones I like but that other people might find strange (oysters and a documentary about an obscure queer icon, anyone?). That’s the beauty of a date with yourself: your input on the activity is the only input that matters! So pick something you adore, and if potential companions might turn up their nose at it, well, so much the better.

Make getting ready a ritual. I often think of getting dressed for dates as a sort of magic spell. I’m adorning myself in totems and trappings that make me feel confident and beautiful: a cute dress, kickass boots, pretty lipstick. This process builds excitement about the date for me in an almost Pavlovian way, so I don’t skip it even if no one else is going on the date with me! This little bit of extra effort could help you elevate a sad, perfunctory night alone into a celebratory occasion.

Bring a diversion of some kind. I always have a book (or my Kindle) with me when I go on a solo date. I also usually bring my journal and a pen, and my phone with some podcasts loaded onto it. While it would absolutely be a power move to eat dinner alone while simply looking around and enjoying the atmosphere of the restaurant, that’s not something I’m interested in doing – it makes me feel awkward, and I get bored. A book can entertain and captivate me in the same way that another person would, if they were sitting across from me at dinner.

Spoil yourself. I know I’m guilty of often thinking I don’t “deserve” nice things, especially if I’m by myself on a mundane Tuesday night or somesuch. But you deserve that extra mile. Sometimes this can be a pricey thing, like a trip to your local fancy cocktail bar or a decadent multi-course meal, but it doesn’t have to be – it could be as simple as adding an extra apple pie to your McDonald’s order, springing for extra butter on your popcorn, or bringing a plush blanket to the park so you don’t have to sit on the damp grass. You’re worth it, baby!

Take photos. We live in an age when it often seems that something only really happened if there are pictures of it on the internet. While this has its pros and cons, the benefit of photographing and sharing aspects of your solo date is that it may help legitimize it in your mind. When you put your meal on Instagram or text a patio selfie to your best friend, you’re saying, “This is nice and deserves to be remembered.” And hell, sometimes those moments can be perfectly Instagrammable!

Stay open to adventure. Many times while on solo dates, I’ve gotten into an interesting conversation with the stranger next to me, or discovered a new hangout I didn’t know about, or tried a new-to-me food and loved it. A beautiful thing about being alone is that you can follow your own impulses; you don’t have to check with someone else first to see if they’re on board. So if you find yourself wandering into a shop with an eyecatching window display, or considering a weird-sounding cocktail on the menu, go with that gut feeling – it could lead you somewhere lovely.

End on a high note. If I skip this step, I often end up wallowing in loneliness, so it’s important to deliberately plan an uplifting ending for your solo date. Mine often involves listening to a comedy podcast on my walk home, or watching something funny on Netflix once I get there. If I’m really absorbed in my book while I’m out, I might continue reading it once I get into bed. Ah, bliss.

Do you ever take yourself on dates? What do you like to do/where do you like to go?