The Art of Solo Dating: There's Levels to This... Which One's Yours?

Ahh, there’s nothing like a good solo date.

As a young mom, sometimes having something to do outside of the everyday routine is the perfect little reset. And when the grandparents are grandparenting, I do dabble in a little nightlife too, LOL.

The idea behind a solo date is pretty simple though: being able to take yourself somewhere, sit at a table alone and actually enjoy being there without feeling awkward just because nobody’s sitting across from you.

But if that does sound a little awkward to you, one thing I’ve learned is that there are definitely levels to this. Maybe you just haven’t found yours yet.

So, let’s get into it.

1. Start Easy

These are what I call soft outings. If you’re new to doing things alone, you do not have to start with the most socially intimidating event you can find. Some of my favorite solo dates are also the easiest ones.

Take the Walk

D.W. Field Park in Brockton is one of those places I grew up going to, and still go to. Headphones, comfortable clothes and a walk or run, that’s really it and sometimes that’s all I have time for.

Parks, walking trails and waterfronts are some of the easiest places to start because there isn’t much pressure attached to the experience. People are walking, running, biking and generally minding their business, which means you can do the same.

Give Yourself Somewhere to Wander

The Rose Kennedy Greenway is another fun option. Start with a walk and figure out the rest from there. Depending on the day, there might be an outdoor market, food trucks, public art or something happening that gives you a reason to stop for a while.

Boston Common works too. The point is just to give yourself somewhere to start without planning the entire afternoon.

Walk around. See what’s happening. Stop when something catches your attention.

Finally Try the Restaurant

You know that restaurant you keep saving? Go.

If you’re not ready for the whole table-for-one experience, start somewhere casual. Sometimes the solo date is simply finally trying the place you’ve been eyeing and finding somewhere you know you’ll be back to.

A walk, somewhere to wander or the restaurant you’ve already been wanting to try is low pressure, easy exit and you can spend as much, or as little, as you want.

2. Give Yourself Something to Do

Okay, now we’re turning it up a little.

A class, a networking event, live music, a community event, this is where there’s an actual time and place attached to the plan or activity. Something where, depending on what you choose, you might not be alone for very long anyway.

I think that makes a difference.

So here’s the trick: start where your interests are.

It may sound obvious, but you’re choosing something you already know you’ll enjoy while also putting yourself in a room with people who chose to be there for the same reason you did.

That’s where the outing starts getting a little more social. And if you don’t talk to anybody? You still did what you came to do.

A friend told me earlier this summer that even though the area feels huge, you’re always going to know someone or meet someone cool.

That’s been weirdly accurate.

I keep running into people I knew growing up, including people I haven’t seen since we were kids, and I LOVE it. But it’s also made me realize that those run-ins probably aren’t as random as they seem. If we haven’t talked in years but both independently chose the same R&B event, networking event or community event out of everything we could’ve been doing that day, apparently we still have something in common.

The same goes for people I’m meeting for the first time. Little by little, Boston starts feeling more familiar.

That’s why going alone can actually work in your favor in spaces like these. Without a friend to stay attached to all night, you’re a little more likely to look around, introduce yourself or have conversations you may not have had otherwise.

3. Lastly, Make It a Production

Okay, now we’re in "get a babysitter for the night" territory. These are the events that social anxiety hates, the ones that you might plan ahead for because they can easily take up the whole evening.

Bent Brunch. Watch parties at The Grove. Concerts. Nightlife. Big social events.

These require a different kind of solo-date confidence because there’s no hiding behind your headphones, and they’re probably the plans most likely to get stuck in the group chat while everyone waits for somebody else to commit.

So, get there at a time when something is already happening when you walk in. The first few minutes might still feel awkward, but when everybody looks like they already know somebody and suddenly your phone becomes the most interesting thing you’ve ever seen, look up and find something to do.

Grab a drink or two if that's your vibe (but remember you did come by yourself, so make sure you can get home by yourself). Talk to someone you recognize or meet someone new. Once you realize nobody is actually paying nearly as much attention to you as you thought they were, suddenly you’re just… there.

Having a good time.

So, Here Are Some Upcoming Events for Any Level

If you’ve been waiting for someone to make plans with before getting out, you don’t have to jump straight to the thing that terrifies you. Keep it easy, give yourself something to do, follow your interests, then make it a production.

You don’t have to become somebody who prefers doing everything alone. That’s not really the point.

You might just get a peaceful afternoon, discover a restaurant you love, run into somebody you recognize or meet someone completely new.

Or you might just go home thinking, I’m glad I didn’t miss:

Trying a New Restaurant

Best for: Keeping it easy

Pick the restaurant you’ve been curious about and just go. I’m taking my own advice and trying the soul food restaurant Everybody Gotta Eat next. It’s located in Cambridge and I’ve been seeing it online a lot lately. No ticket, no itinerary and no pressure—just somewhere new to try, and the food looks delicious.

Mid-Autumn Lantern Festival

Best for: Wandering at your own pace

September 12 | 10 AM–5:30 PM | Boston Chinatown

Food vendors, street shops and live cultural performances throughout the day make this an easy one to explore however you want. Stay for an hour or make an afternoon out of it.

Art Girl Walk: Take Up Space Tour

Best for: Guided exploration of city art

September 12 | Downtown Boston → Rose Kennedy Greenway | Free

A guided downtown art walk featuring four large-scale works by women artists of color, followed by a Greenway celebration with music, food trucks and lawn games.

Last Lap Yoga

Best for: Giving yourself something to do

September 16 | 5:30 PM | Pope John Paul II Park, Dorchester

An outdoor yoga class with Last Lap Boston. Bring a mat and flow with the group—no figuring out what to do once you get there, because the activity is the plan. A good one if you’re ready to move past the soft outing but still want something structured and low-pressure.

SILK at Tall Ship

Best for: Making it a whole production

September 20 | 3–8 PM | Tall Ship Boston

An afternoon of R&B with Real P, Baby Indiglo, Mez.Wav and special guest SuperSmashBroz. Put the outfit on and go. If R&B is your thing, you’ve already found your crowd.

Let’s Dance Boston

Best for: Getting outside your comfort zone

September 23–27 | Dewey Square

Five nights of live music and social dancing, including Salsa, Latin Afro-Caribbean, Hustle, Lindy Hop and Soul Line Dancing. Each night starts with a free 45-minute lesson, so you already have something to do when you get there.

I’ll keep adding the places, events and little discoveries I find along the way. And if there’s somewhere around Boston you’ve been wanting to try but haven’t because you don’t have anyone to go with yet, send it my way.

Maybe I’ll go first.