Taking yourself on a date is one of life's great pleasures. If you haven't tried it before, here are 8 ideas to get you started, from rank beginner, all the way up to taking yourself out to dinner at a Michelin star restaurant. Let me know your ideas in the comments!

Take yourself on a date!

“Oh, I can’t do that. I don’t have anyone to go with.”  If you’re like most of us, there’s a band, film genre, activity, or cuisine that you love and no one you know can stand. And, if you’re like a lot of people, you’re probably stopped doing that thing that you love, because you think that it’s something that you can’t do by yourself. I’m here to tell you that unless what you really want to do is go on a teeter-totter, there’s very little that you can’t find a way to do on your own. So go ahead, take yourself on a date.

If there’s a bright spot from the last two years, it’s that we’ve gotten a lot more used to our own company, though perhaps we still have some things to learn about how to enjoy it. We can leverage that skill we’ve developed to be brave and get out there. Pick something from your I Love This List (you made one, right?) and take yourself on a date.

A useful skill, regardless of your relationship status

The ability to take oneself out on a date is, I believe, an essential life skill, no matter what one’s relationship status is. To be comfortable enough in one’s own skin to go out in public and do something that one wants to do, even (especially) if no one else one knew wanted to do it is key to a healthy, fulfilled life. It helps to take the pressure off of relationships, if we aren’t reliant on others to be able to do the things we want to do. We won’t resent others if they don’t want to do what we want to if we’re confident enough to do things on our own.

A lot of people ask me how I can have a good time as a solo traveler. It starts with taking yourself out on dates and works up to grand adventures.

Take yourself on a date to a wine tasting class
I took myself on a date to a natural wine class at Dear Annie, Cambridge, Massachusetts

Getting some practice in taking myself out on dates

This past week, I’ve been getting in some practice taking myself out on dates again. In the Befores, I excelled at this, but it has been a while. I’m in the middle of a busy week!

Sunday, I went to another round of storytelling at Grendel’s (Odds Bodkin told us tales about Thor this time). A natural wine class at Dear Annie (if you don’t know yet, check out my Boston, Cambridge, and Somerville guide) caught my eye for Monday. I learned a thing or two and then stayed for a piece of pizza (Monday night’s pizza night). I’ll admit that I’m a bit out of practice sitting in a room full of people talking to friends and not talking to anyone, but my skill quickly returned.

I’m going to an event at the Gardner tomorrow evening (Third Thursdays are now First Thursdays), a book event on Friday, and a concert on Saturday. I’m taking myself out on all these dates (a friend might join me at the Gardner), and I’m having a great time exercising my long-lost skill.

Take yourself on a date! 8 ideas from beginner to expert

Here are eight ideas to inspire you to take yourself on a date, ranging from a simple trip to a café to taking yourself out to a fancy dinner. Be sure to share any of your ideas in the comments below!

1. Absolute novice: take yourself on a date to a café

If you’re really, truly uncomfortable doing things by yourself and you think a movie is too big a commitment, try this. Grab a book, go to a café you like, order a coffee (or whatever else you’d like), sit down, and read your book while you drink your coffee. People go to cafes alone all the time, and no one ever gives them a second thought. Before you’re ready to leave, sit for one minute without looking at your phone or your book. Just look around the cafe, observe, and breathe.

Congratulations. You just took yourself on a date.


If you feel uncomfortable, consider going during an off-peak time. That way, there will be plenty of seating and fewer people

2. Beginner: take yourself on a movie date

If you’ve never gone to a movie by yourself before, you are missing out on one of life’s true pleasures. No need to agree on what to see, no one talking to you during the film, and you get to pick your own snacks. I started going to the movies by myself in my early twenties, and I now prefer it. We have a culture that associates movies with dates with partners (for understandable reasons), but if seeing the movie is really what interests you, going on a date with yourself to the movies is the way to travel.

Last month, after two years away from the movies, I sat in the balcony of the Brattle Theatre, for a screening of Casablanca. Among my friends, I’m the Casablanca fan, so I go to screenings alone. I had a fantastic time.


If the theatre offers advanced ticketing, and you feel uncomfortable, show up just before the film starts

3. Beginner: Go on a date with yourself to a museum

There’s an exhibit at your favorite museum of an artist you love, and no one wants to go with you. Don’t miss it—just take yourself on a date to a museum. Going to a museum solo keeps your focus on the artwork. You can go at your own pace and see as much or as little as you’d like, and no one is going to get upset or cranky.

At the Museum of Fine Arts, Boston, there’s a painting of Saint Francis by the Spanish artist Zurbarán that I’ve spent hours and hours staring at over the years, staring when I used to be able to get in for free with my college ID. I can’t really tell you why, but I absolutely love this painting. I also find a lot of solace sitting with the Buddhas and there are other items in the museum’s collections that I try to visit when I’m there solo. When I’m with friends, we tend to stick to the main exhibit and possibly a wing or two. I enjoy those visits a lot, but they aren’t the same as me getting my very specific art fix.


For added fun, consider a "museum at night" event, if you museum hosts such things

4. Intermediate: Go on a date with yourself to the theatre

Along the same lines as a movie, but a little more down time, a theatre performance also offers another great opportunity to go on a date with yourself. As with a film, you don’t need to negotiate the type of play—do you love musicals, and your friends can’t stand them? Perfect. Or, maybe you love the ballet.

This is a little bit more formal than a film, so it’s up the scale a bit. The same tip applies, though. If you feel more comfortable showing up just in time to be seated (obviously don’t be late—you might not get seated), that works here, too.


You can sometimes score last-minute solo theatre tickets. Check your box office or website for specifics

5. Intermediate: take yourself on a date to a concert!

Go see that band you love. You know you want to. Instead of trying to convince one of your friends who doesn’t hate the band to go with you, only to have a so-so time (and perhaps ruin your good time), get yourself a ticket and go yourself. Dance. Whoop (if that’s appropriate). Have yourself a great time.

This one is a little bit more of a commitment than a movie, because it involves a fair amount of milling about time, and there’s more time to feel self-conscious. There’s a couple of ways to deal with this if it’s your first time. If it’s an event with assigned seating, you can show up with just enough time to get to your seat.

If it’s general admission, and you want to be sure to see (and you’re on the short side like me), you might want to get there in enough time to stake out some territory (though it’s easier to move around when it’s just you).


Be careful with alcohol. See general safety tip below, and definitely never leave a drink unattended

6. Intermediate: Take yourself on a lunch date

You’ve gone to a café, now take yourself out on a date to lunch. Someplace decent, maybe have a couple of courses. Sit up straight, put your phone away, and have a proper lunch. People have lunch by themselves all the time, for lots of reason, and you’re far more likely to be the only solo diner.

This is a great time to practice more mindful eating. Eat slowly, put your utensils down between each bite. Pay attention to what you’re eating. It’s a good practice, especially after a couple of years of eating by ourselves at home.


If you’re really feeling a little bit weird about eating lunch by yourself, take a long lunch and go on a weekday. It’s far more common to have solo diners having lunch on weekdays

7. Advanced: Take yourself on a dinner date

Taking yourself out on a dinner date takes a little courage, but yields great reward. It’s a different experience—you can spend more time noticing what you’re eating as opposed to focusing on conversation. It also allows you to cultivate a little air of mystery about yourself. If you’re having a lovely meal and just enjoying  your own company, you are far more likely to elicit envy and admiration, and anyone who feels sorry for you doesn’t know what they’re missing.

If you haven’t done this before, it can take a little practice, and you might feel a bit awkward the first time you do it. That’s why we have a couple of levels here.

Whatever the level, dress appropriately, hold your head up high, and don’t stare at your phone the whole time.

Level 1: Sit at the bar

Solo diners can usually find a spot at the bar for a meal. It’s a low-key experience, and not unusual for people to do this solo at all. Maybe you’re traveling on business or breezing through town. Your fellow bar companions aren’t going to be staring at you as an object of pity (unless, of course, you order a bunch of tequila shots and start dancing on the bar).

People at the bar tend to be friendlier, so if you’re worried about feeling lonely, you might be in for a pleasant surprise (it’s also totally fine to just keep yourself to yourself and eat your meal in peace).


This works great for last-minute decisions, but popular spots are likely to have people with the same idea. You might have better luck showing up a little later or a little earlier than peak time.

Level 2: Dine at a table

Remember how we did this for lunch, and you had a wonderful time? Now’s the time to test your skills and have dinner sitting at a table. Order at least a starter and an entrée, and get dessert. Take your time between bites. Observe your surroundings. Sit up straight.

Unlike dinner with others, a solo dinner is a highly introspective experience. It can be highly relaxing. It also takes a bit of practice if you aren’t used to it. Try it at least a couple of times. My guess is that you might find that you really enjoy it.


If you want a table, make a reservation whenever possible. And then make sure to tip your server well if you're in the US

8. Expert: Take yourself out to a fancy dinner

When I went to Budapest, I booked a table at Onyx, which had 2 Michelin stars (sadly, it has been on hiatus since the pandemic. They are now undergoing renovations, and it looks like they plan to reopen). I’d been to nice restaurants before, but this one definitely took service up a notch. I had a little stool for my handbag. I was helped with my coat. There were white gloves, and I had a main server, the sommelier, and others attending to my meal. I don’t think I’ve ever had more fun at dinner before in my life.

I was the only solo diner in the restaurant. I paid attention to every bite, from the little breads with pumpkin oil to the forest fruits dessert, and every sip from Champagne to an aged Hungarian spirit. The dining room, all in blue velvet and understated elegance, was somehow both comfortable and formal at the same time.

It took me a fair amount of practice to work up to feeling comfortable dining solo for such a meal, but it’s one of my favorite travel memories. And, I will tell you that I definitely had more fun than the couple quietly arguing, and another couple wolfing down their food (maybe they were in a hurry?).


Do a little homework about whether or not the restaurant is a good pick for solo diners before making a reservation

A few pointers for taking yourself on a date

I have a motto when it comes to solo activities: Be Brave, Don’t Be Stupid. We want to have a good time and stretch ourselves, not wind up a cautionary tale.


Not every activity is suitable for a solo date, but the ones I’ve suggested generally are.

  • Use your judgement with late night activities and the like.
  • Do a little homework before you decide to do something.
  • For those of us carrying handbags: graduate to a cross-body, and keep it on you at all times (exceptions are finer dining, but even then, don’t lose sight of it).
  • Use general street smarts. Mind any drinks and food (this is important—don’t leave a drink unattended, ever, and don’t take drinks from strangers).
  • It doesn’t hurt to let someone know where you are (you probably don’t need to do this going to a museum for the afternoon, but you know what I mean).


Learn from my mistakes. Especially in my youth, I did not follow the advice I’m about to dispense, but this is an important one when hanging out by yourself: watch it with alcohol. It’s a tempting crutch, but it won’t help you. By all means, have a drink. Have two, especially with a meal. But use caution and see the point above about never leaving your drink unattended. You want an air of mystery, and there’s nothing mysterious about getting all sloppy.

What are your ideas for taking yourself out on a date?

Have you ever taken yourself out on a date? What’s your favorite thing to do? Let me know in the comments below. Be sure out the other Happily Single posts and more on the Happily Single page!