"New beginnings are often disguised

as painful endings." -Lao Tzu


I will spare you the gory details of my own personal sob story. This is not a Nicholas Sparks heartbreak novel or a Shakespearean tragedy filled with death and unrequited love. This is not a tale about the breaking, but of the putting back together.

However, to shed light on this journey’s origins, I suppose I must provide an historical element to give it perspective.

Mine is not a magnificently unique story of bitter misfortune or woefully doomed romance. It’s pretty universally standard: Boy meets Girl (me), Girl and Boy start dating after two years of flirtatious friendship, Girl and Boy date seriously for two more years, Boy takes Girl on important trip to meet all of his family. Girl then naturally wants to start planning commitment of the matrimonial kind.

Boy says no. Girl confused.

Boy says he’s not sure and needs more time.

Girl says that’s bullshit.

Boy and Girl cannot agree and see everything going downhill fast…romantic checkmate, if you can imagine.

Girl and Boy Dufus decide to call it quits before they despise each other and irreversibly wreck each other’s mental health, emotional state, and ability to function like normal adults.

Was it mutual? ―Yes. Fault (and ultimately agreement) was found on both sides.

Do I resent the assessment that I wasn’t “forever” material? ―Very. Much. So.

Do I regret the decision to split up? ―No, but that doesn’t dull the inevitable shitty aftermath of pulling shattered pieces of myself back together.

That’s all I’ll say about the actual break-up, because it doesn’t matter. The relationship was over. The ugly details of how and why don’t matter. That’s not what this story is about. As two wise writers wrote succinctly, it’s called a break-up because it’s broken[1] and it was time to move on.  


Now what?

Well, everyone does things differently. In years past, when relationships ended in agony, I’d just go out and party until I found a suitable male proxy I cared less about. I thought, now that I’m twenty-seven and have my shit together (i.e. career, home, friends, stability, cable television and the DVD box set of Mad Men Seasons 1-5) it might be time to try something different. 

The most immediate suggestion from everyone was, “Just do online dating.”

While not horribly opposed to the ever popular cyber route, I hate that people of my generation proclaim there are only two options for a single person: A.) Go to the bar and drink with strangers until you fall into the lap of someone who can tolerate you, or B.) Sign up for an online service which requires completing ridiculously lengthy questionnaires until you find more quality dates with like-minded individuals, who end up tolerating you.

I wanted neither. I wanted a choice C.

I’ve dated lots before, especially while in college. I used to joke that dating was my Olympic sport. But now, after pouring myself into a relationship I was truly ready to commit to forever, I decided to focus my energies inwardly and not rush to the first penis—I mean opportunity—that came my way.

I didn’t want to date anyone. I didn’t want to sign up for any website. I didn’t want to go out and have meaningless rebound flings. I just wanted to do my own thing again. Be me again, not someone attached to the hip of someone else who after a few years was still allegedly trying to decide whether I was worth his time or not.

Um, fuck that.

Predictably, UPS didn’t immediately knock on my door with an emotionally-available Chris Hemsworth look-alike replacement boyfriend. I had to consider other options. No, not girls. I don’t think that’s really a switch one can purposefully control. I’m not ignorant of the female prospect, but it’s never been, how shall I say it, a flavor of ice cream I’ve ever found myself wanting to try. However…

Hang on…I’ll…

I’ll date myself.

That’s what I’m going to do.

Behold choice C! Date yourself.

This epiphany became quite a preoccupation. In the months post-break-up my friends and coworkers would say, “Hey, are you seeing anyone yet? I’ve got someone who might be interested.”

My reply became a repeating chorus: “No thanks, I’m dating myself.”

It is not necessarily a novel, brilliant idea. People date themselves all the time, i.e. last week when you took a “mental health day” to binge-watch TV for fourteen hours in your sweatpants (You know nothing, Jon Snow!). I feel like it is common knowledge that after any type of loss a person should act selfishly in order to heal, but I wasn’t going to be so unconvincing. A few days on the couch watching sci-fi movies coupled with one discount spa pedicure wasn’t going to cut it. I was going way bigger.

I typed up a “List of Dates” to take myself out on—fifty of them. That’s a good number, right? It comprised of things in the city I had wanted to do that I didn’t have time for before, places and events to experience, spirits to drink and foods to eat, challenges I didn’t have the balls to face, afternoons and evenings to relax and watch the grass grow. Coming up with fifty different ideas proved challenging, and after finishing the List, and printing it out, I looked at it and thought—Shit, this is gonna be tough. Even if I did one of these Dates every week it would take me about a year to finish.

I didn’t care. It wasn’t about the time in which to complete it all, this wasn’t a race. There’s no crash course for heartbreak, and there wasn’t a participation trophy. So why was I doing this?

The alternative was to continue reveling in self-pity, resentment, anger, and extreme unproductiveness, or worse―crawl back to Can’t-Make-Up-His-Mind Ex-Boyfriend. In the memorable words of Jennifer Aniston’s character Brooke in the movie The Break-up—I deserve someone who gives a shit.

No, no, forward was the only direction to go. This was my constructive, unwaveringly bold attempt at jumpstarting myself. This was my new mission.

Anecdotal evidence: My friend Susan (celebrity casting: Susan Sarandon) had gone through a divorce with her husband of twenty-ish years. Their two kids were in college. They sold the house they shared in all that time. She got a place of her own. He did too. They spent time apart trying to put their lives back together. Then one day Susan announced, “Guess what! We’re back together!”

Um, what?

Susan explained everything. She spent some time alone, got herself back on her feet, and was feeling whole enough to try dating again. The Fates would have it that she and her now ex-husband signed up for the same online dating service. And they matched with each other. And they went on a date with each other. And she said: “It was a complete new start, like when your computer screen goes blank, you know that Blue Screen of Death, and the only thing you can do is unplug it. Turn it off and turn it on again. That’s exactly what it was like. A reboot.”

I pondered her words with amazement. They resonated with me profoundly. In all of my girlfriends’ lengthy histories with men I had never heard anything like it before. She went on, “I’m so deliriously happy, and I wish this happiness for each of you,” pointing to the rest of our group of friends.

Now, my own personal rebooting will definitely not include a similar reunion with Dufus. Sorry, spoiler alert.

To add to the initial disclaimers, this is not a self-help book. I am not telling you to do this to get over your break-up, or whatever else you are going through. I’m not a counselor, relationship expert, life coach, psychotherapist, psychiatrist, palm reader, or other type of medium. I am, however, a recently-heartbroken full-time-working registered nurse a few years shy of thirty, whose top qualities include a flair for story-telling, beer-drinking, and shenanigan-seeking in and around Portland, Oregon’s quirky present-day single scene.

Honestly, I’m simply a person logging my attempt at trying something new. This is what I did and how I did it, and why I did it. You may decide this is a stupid idea. You may decide to do something similar or completely different. You might make a list of fifty different mountains to climb, fifty different gourmet cheeseburgers to consume, or fifty dates with fifty different people of your preferred gender(s). In any case, I hope you have health insurance.

Further warnings: Sometimes I swear. Sometimes I delve into the intimate parts of my life or others. I’d say this narrative is somewhere between PG-13 and definitely don’t read aloud to conservative Grandma. Sometimes I hyperbolize but it’s my account, not someone else’s to fact check; I swear these things really happened. I couldn’t make this shit up if I tried. I’ve changed people’s names to protect their anonymity/sanity, but also because it is super hilarious to typecast friends, family, and strangers into celebrity molds. I might have an problem.

You might be reading this because you know me and saw my List of Dates and want to see how it all played out. You might be reading this because you broke up with someone and you are also wondering how to get yourself off the couch (Step one, get off the couch). You might be reading this because I need someone to edit, or you might be my mom.

The point is this is the story of my Reboot. I went on fifty Dates with myself. Some of them were so successful I continue to repeat them; others made for one-time-only specials. I hope it reads as a mix between a blog of bonafide self-indulgence and a journal of new adventures in the uncertain realm of being single and unattached, sprinkled with side stories of inappropriate hilarity.

I sincerely hope you enjoy hearing about it at least half as much as I enjoyed living it.


Marie MacMillan

[1] It’s Called a Break-up Because It’s Broken: The Smart Girl’s Break-up Buddy, by Greg Behrendt and Amiira Ruotola-Behrendt, 2006. See Appendix A.


*The Reboot: 50 Dates with Myself  won 2nd place in the Pacific Northwest Writers' Association 2017 Literary Contest in the Memoir Category. More info here.

Contact info for Marie MacMillan can be found on this website at the top under ABOUT.