Dating Yourself

We’re back! After a restful few days in Lake George, I ended up flying home while Sam spent a little time with his family in New Jersey and a few days in New York City by himself before taking the train all the way back to Seattle (a solid four day journey). If you know Sam, this isn’t surprising; he loves trains. When he’s gone, I quickly revert back to my single gal days of eating veggie quesadillas for dinner (over and over) and staying up working later than I’d like. We would talk on the phone often as Sam would narrate his very full days in New York City and the stops and layovers he had while on the train. After a few days of me lamenting the fact that I wasn’t there to experience it all with him, he encouraged me to ditch the quesadillas and do something special for dinner. See a movie. Go to the museum for just an hour. In short: I needed to get better at dating myself.

I love seeing new things, trying new restaurants and traveling just as much as Sam. But I’m not as good at going it alone; I like to experience things with other people. I always romanticize traveling alone and then when I’m in the thick of it, I realize I’m not the biggest fan. Sam’s the complete opposite, and I both envy and adore the way he approaches solo days alone. As an example, his first day in the city looked like this: a visit to the Brooklyn Farmacy for egg creams (it was terribly hot in New York that week), checking out Book Court for a few new books, and visiting both the City Reliquary Museum and the Museum of Arts and Design. He had a veal meatball pizza at Co. for dinner, a nice long walk through Chelsea, and got some reading done back at the hotel. During a layover in Chicago a few days later, Sam told me all about his pork belly and kimchi biscuit breakfast at The Little Goat and, later, his stopover at the Palmer House Hilton for coffee, a Manhattan and postcard-writing. The man is good at dating himself.  I have a lot to learn.


I’m not going to lie and tell you I began cooking more elaborate meals after his nudge — that simply didn’t happen. I also didn’t get to the museum. Or take myself to a movie. But the weather in Seattle has been absolutely summer-perfect (sunny mornings and long, long days) that a milkshake seemed in order. It needed to be a really special milkshake with farmers market berries and an afternoon catching up with the paper. I picked up some vanilla bean ice cream and we had already had a bit of leftover buttermilk, so late in the afternoon last Sunday, the time had come: it was time for a solo date.

I turned on the oven to roast the berries (while it may seem initially fussy, this is the only way I do strawberry milkshakes these days — it draws out their natural sweetness and elevates an everyday milkshake to something quite special), fetched last week’s newspaper  and the pile of mail I was still sorting through and sat down at our kitchen nook. There was a postcard from Sam that he’d written while sitting at the counter at the Brooklyn Farmacy. There was an interesting piece on mermaids and a 36 Hours in Munich that made me itch for travel. And that milkshake: sweet roasted strawberries, speckled vanilla ice cream, and slightly tart buttermilk all coming together in one thick, delicious summer milkshake. For that one afternoon at the very least, I feel like I started getting the hang of this dating yourself thing.

Roasted Strawberry and Buttermilk Milkshakes

Roasted Strawberry and Buttermilk Milkshakes

  • Prep time: 10 mins
  • Cook time: 30 mins
  • Total time: 40 mins

I first started roasting strawberries with a little balsamic vinegar after reading about the method from Heidi Swanson of 101 Cookbooks, and I haven’t done it any other way since. The vinegar draws out the dark sweetness of the berries and the honey balances it beautifully. It’s a good idea to select strawberries that are roughly the same size — this way they will roast evenly. If your berries are quite large, feel free to quarter them.


For the Roasted Berries:

8 ounces (1/2 pound) small to medium strawberries, hulled and halved
1 tablespoon extra-virgin olive oil
1 tablespoon honey
1 teaspoon balsamic vinegar

For the Milkshakes:

1 cup / ½ pint vanilla bean ice cream, plus more for a thicker shake
½ cup buttermilk
heaping 1/2 cup roasted berries (see above)


Roast the berries: Preheat the oven to 350°F. Line a rimmed baking sheet with parchment (you don’t want the juices to run off and muck up your oven).

In a medium mixing bowl, whisk together the olive oil, honey and vinegar. Add the halved strawberries and toss to combine.

Turn the berries out onto the baking sheet and roast until they’re soft with the juices just beginning to thicken –but not burn—about 25-40 minutes (really depends on the size of your berry halves). Scoop the roasted strawberries and juices onto a large plate to cool.

Prepare the milkshakes: Using a milkshake maker or a blender, combine all of the ingredients and blend until combined. If you like a thicker shake, this is a good time to add an additional scoop of ice cream. Serve in your favorite glasses. Enjoy immediately.

(Note: Remember this breakfast recipe using roasted strawberries? I think you’d like that, too)


  1. abby

    I was single for a lonnnng time and got used to being alone and doing things alone or with girlfriends. Now that I'm married, I find it's sometimes hard for me to get out of my single-gal/must be busy all the time mode! I love being on the go, but sometimes it's nice just to relax at home :)

  2. Sam @ The Second Lunch

    Oh, this is wonderful Megan. It's not that I don't enjoy doing things alone, I just have quite a hard time *allowing* myself to do things alone – my biggest hesitation is always the flawed thought process that I don't want to experience things that others don't get to experience. (Even if it's because that they don't actually like doing these things.) I've been trying to remedy this, because I think that more often than not it means that I'm not doing the things I want to do. I actually have this "to-do" on my summer list: "Make a list of by myself activities, and then do them."

    1. megang

      I LOVE that you have a "to do" list of solo activities. God that sounds like something I would do; in fact, now that you've put the idea in my head ... I think I'm a little different in that I really always want to share experiences with others so I find myself not appreciating them nearly as much as wishing ____ were there to see something, try something, taste something. Probably not a great sign that I can't find the pleasure in it solo. I'm going to put that on my summer "to-do" list :) Hope you're surviving that East Coast heat! ~mg

  3. Mallory

    It is so refreshing to know that I'm not the only one that loves the thought of solo travel but when in the midst, wish for company. I have zero problem going to movies and the such alone, often I find myself enjoying it more.... But I can't get myself to go and eat a dinner out...I envy those that can do it with such ease..even though I'm sure it's easier in NYC than cleveland Ohio....have a great weekend and thanks for a great post!

    1. megang

      Hi, Mallory-
      Gah! Why is eating out alone so hard? I remember when I was in graduate school I went on a little solo work retreat to Cape Cod and was super excited about it ... until dinner when I couldn't seem to get up the gusto to try the restaurants I'd wanted to try. Hope you're staying cool in Cleveland!

  4. Shanna

    It's sort of ironic that, reading this, I am thinking, We're so much alike! We would have so much fun hanging out!

  5. Christa

    Lovely post. I'm going to try this recipe :)

  6. Denise | Chez Danisse

    I love this idea of roasting strawberries. And you used buttermilk! This shake looks superb, Megan.

  7. Sarah

    Roasted strawbs are ma world. This buttermilk shake looks amazing.

  8. ileana

    The mermaids! My boyfriend works at the Hernando bureau of the Tampa Bay Times and recently interviewed a retiring mermaid. She's in her 30s. Anyway, I hear you on being better at dating yourself. I get so lazy with dinner sometimes if Danny is out covering a late school board meeting.

    If it's more than a day going solo, I tend to turn to old favorite movies to keep me company. (Dirty Dancing! Amelie!) Taking yourself out for a nice lunch is a good move. :)

  9. thelittleloaf

    I think it's so important to be able to spend time in your own company and cooking great food is the best thing to do! This shake looks divine - I adore roasted strawberries.

  10. nicole

    Oh -- I love this. I used to be better at taking myself out on dates but lately that has fallen by the wayside ... I have some alone-time coming up in the next few months and I think I will revisit this. Love the spirit of it; even if you don't get to squeeze in an afternoon museum-wander just treating yourself to a little something special makes all the difference. xo

  11. lori

    This milkshake seems like a perfect date for one!

  12. Kristin

    Loved this, Megan. All of it.

    PS: Buttermilk in a milkshake?! Yes.

  13. Lecia

    These sound incredible, Megan. Can't wait to try.

  14. Molly

    Given the title I thought I was going to be reading a recipe for a milk shake made with dates. Balsamic roasted strawberries sounds might tasty, though. Learning to enjoy being alone is definitely a learned skill. I love having me-time and I've never quite gotten the hang of bringing a book to a restaurant. There's so much to see!

  15. Kasey

    What a fantastic way to start my week..I'm admittedly terrible at dating myself. I think I used to be better, though dating still probably meant 'work.' Love this reminder and the sound of these milkshakes...oh, roasted strawberries...

  16. kickpleat

    I'm also pretty awful about doing things on my own. But afternoon movies in a cold, dark theater? I'm there. That's one indulgent alone-time pleasure for me!

  17. Jeb

    Oddly enough, "dating myself" has involved a walk to Brooklyn Farmacy for a maple egg cream. Quite, quite delicious!

  18. Lindsey

    I have been trying to learn to date myself for a few years now... Even just entertaining my early-rising-self on weekends when my husband likes to sleep in used to be so hard for me, but I'm getting better. I am still not good at going to restaurants or movies alone, though!

  19. molly

    oooo, yes, buttermilk + strawberries, blitzed together! we do something similar, though veer more toward smoothies, with a frozen banana, maybe mangoes, plus orange or lemon (juice) for zip. and lots of ice cubes, for chill. so good.

    welcome home, megan. slurp up that seattle summer while you can. it may be short, but it's oh so sweet.


  20. olga

    Book Court is a block away from me!!! :)

    1. megang

      Olga! I was thinking about you when we were there, actually. While Sam was there for a good chunk of time, I wasn't there for long at all so we tried to jam it all into a little over a day or so ... next time, I'd LOVE to finally meet in person!

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