An Annual Letter to Yourself

Letter to Yourself

Since 2003, I’ve written a letter to myself that I don’t open until 12 months later. In the letter, I reflect on the previous letter, the previous year, and what I hope for the next year.

The letters are always personal: I’m literally addressing a future version of myself who is both the same as who I am now and also very different. It’s awkward that first year, but it’s been one of the most rewarding things I’ve ever done for myself.

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Christmas for singles

Christmas for singles

Christmas for singles can be wonderfully fun, tortuously sad or both on any given day.

The day after a big holiday can be difficult if you’re flying solo, whether you celebrate or not and whether you’re surrounded by family or not.

So, this DY Friday, focus on taking care of yourself.

What do you want to do today and this weekend? What would feel exquisite, luxurious and fun? What does your body, mind or spirit need in the next three days?

Give yourself the gift of care today.

Go to the Hardware Store

Hardware store

This may be one of my strangest suggestions for a DY Friday yet, but bear with me.

Today, or this weekend, take yourself to the nearest hardware store. When the salesperson asks if you need help, just say “No thank you” or “I’m just looking.”

Then, wander every aisle.

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Take a Picnic


Right out of the cheap date ideas book: take a picnic.

Grab whatever you were going to eat for dinner and head outdoors. Go to a park, community garden, mountain top, or even just your own front door step.

Bonus points for making an elaborate meal for this experience.

Bonus points, also, for going low-key: grab whatever snacks are around the house (crackers, cheese, trail mix, hummus, leftovers, etc.) and create a veritable smorgasboard out of this picnic!

Real Cities for Real Women

Real cities

There’s a new round of “Best Cities for Single Women” lists going around, but I LOVED this response from Refinery29, “a new-media brand for smart, creative and stylish women everywhere.”

“The REAL List of The Best Cities for Single Women” starts like this:

“Why do the “Best Cities for Single Women” lists always put the availability of single men as their top deciding factor? Man-snagging isn’t everyone’s number-one priority, and don’t even get us started on how unhelpful these lists are for queer gals.”

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A Stroll at Sunset

Stroll at Sunset

A quintessential, even stereotypical, date activity is taking a stroll at sunset. It’s seen as the height of romance with a loved one, but today I encourage you to find the romance in this activity on your own.

Think about a place to take a sunset walk (lake shores, bike paths, any place with a long view toward the west is a good option). Prepare a little pack with appropriate clothing, some hot cocoa (or a cold tea), maybe a blanket and a book.

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A Writing Project on the Past Lives of Antiques


I once read a date suggestion that seemed unique: go to an antiques store and ponder the past lives of what you find.

So, dear reader, consider taking on this challenge:

Find an antique shop and discover a piece that really speaks to you. Immediately decamp to a coffee shop, library or other nearby place and write a piece of fiction about the object.

The story can be short or long, pure fiction, sci-fi or any other genre. You can take a photo of the piece to revisit while you’re writing.

Who owned this piece? How did they obtain it? What did they do with it? How did it end up in this antique store? Let your imagination run wild.

Consider this a stretch of your creative muscles, a new way of shopping, or just a micro-adventure to enjoy.


Prepare for Thanksgiving


For many of us without significant others (only our significant selves), Thanksgiving can be a bit awkward. Around the dinner table, you could get questions from family about who you’re seeing, or you could run into old flames. You could find yourself flying solo for the holiday or receive invitations from friends or coworkers.

Take some time to prepare for Thanksgiving. Visualize the best version of what could happen and “practice” the visualization multiple times.

Maybe you need a witty comeback for the sardonic aunt or uncle who’s always prying into your personal life. Or maybe you want to have a heartfelt conversation with your gram or gramp about their lives before each other.

You could plan to accept or decline certain invitations for next week. And you can even plan some treats (or, elaborate adventures!) for yourself so you don’t feel like there’s celebration lacking in your holiday celebrations.

Don’t let Thanksgiving overwhelm you, no matter your plans. Take a hold of the holiday and make of it what you will.

Laugh It Up


This Dating Yourself (DY) Friday, laugh it up. Find a comedy show and put it on your calendar. With any luck, you’ll find something this weekend, but even if it’s a few weeks from now, commit to some live comedy in your life.

If your scene is totally devoid of local, live comedic talent, check the listings for a larger city. Or, find a comedy movie playing on the big screen, even if it’s a genre you don’t normally consider.


Like a Tourist


Experience your town like a tourist. Take a walking or bicycle tour. Follow the directions of a self-guided historical or architectural tour.

For a full weekend of activities, Google your state, town or city tourism commission and request a tourism guide.