Shopping For A Little Black Dress

“I think I’m going to be single for the rest of my life,” she said matter-of-factly, with only the slightest hint of frustration. It wasn’t the first time I’d heard her say that. She said that same exact thing, word for word, about two hours earlier when we were waiting for our table at the O.G. (the Olive Garden, if you aren’t in the know).

“Why do you keep saying that?” I asked her.

“Because. Dating’s a drag.” I couldn’t argue with her there. Based on my own experience, I had to agree with her.

Now mind you, this was a conversation I was having with my then seven-year-old niece. But hey man, she wasn’t wrong. Dating is a drag. Or at least the way I was doing it. I was putting in a lot of time, energy, and effort into the situation and was getting jack smack in return for all of my troubles. I was going on one stupid first date after another and not having much in the way of luck or fun. I was ready to throw in the towel, throw my hands up in the air and say, “Fuck this noise. I’m out.”

Friends were telling me that I wasn’t giving it a fair shot, I was giving up too soon, I needed to broaden my search criteria, blah blah blah. But it just didn’t feel right to me—mainly because it just felt shitty. It was giving credence to all of the single-post-thirty-fears: I waited too long, and now I’ve missed my chance; I let that good one get away; I spent too many years with that wrong one; all of the good ones are taken, and now I have to choose from the leftovers. They may not be interesting, they might not be upstanding members of society, and you may never, not ever want to live in a world where you are expected to make out with any of these dudes, but these are the guys in your area code who are (arguably) available for you to choose from. I have to say, sometimes dating in your thirties feels like going to a nice department store and only being allowed to shop in the clearance department. The whole thing felt like an exercise in getting good with settling.


Then I came across a great metaphor while reading an advice column (I’m a liar; my Aunt Margaret actually cut it out of her local paper and sent it to me. I never read those things on my own.) The author discussed the difference between actively looking for that someone special versus circulating but letting it happen naturally and compared it to shopping for a little black dress (Boys, feel free to sub in the outfit of your choosing for this metaphor):

If you are looking for a dress because you need to wear it this weekend, yeah, you start your search knowing exactly the dress you’d like to have. But towards the end of the week, you’ve seen a bunch of dresses, none of them were what you are looking for, and you officially hate shopping. But you really want a dress for this weekend so, even if you haven’t found your ideal dress, eventually you grab something acceptable and buy it whether you’re crazy about it or not.

Now let’s say you are looking for a dress because you’d like to have a new dress but, hey, no rush. First off, you are no longer on a mission, so you don’t run the same risk of rationalizing the way you did when you had that sense of urgency. You are willing to hold out until you find what you are looking for. You can see a hundred dresses and keep it moving because none of them were quite right. And you do other things with your time other than going shopping for a dress because, hey, no rush.

Anyone who has become frustrated by not being able to find what they are looking for has heard from a well-meaning friend, “It always happens when you stop looking.” And then usually someone else always chimes in, “I know! It’s so true!” And it is true. Because, if you’re doing it right, not looking involves you actually doing things with your time that go beyond creeping around bars and the internet looking for dudes/ladies/whatever you’re into. You have to not only really commit to not looking but actually LIVING YOUR LIFE, doing things that make you happy, having fun, giving yourself something to smile about when you look back on this time in your life. It’s when you are living your life—making the best of your current circumstances and having a blast doing it—that someone sees you from across a room and thinks, “That person looks like they know how to have fun. They look interesting. I want to talk to them.”


Fun fact: Trying new things often includes meeting new people. If you lean into your passions and find the fun, I bet you’ll also find some other like-minded people. I’ve been leaning into my hobbies and I can tell you from recent personal experience that I have had more positive run-ins with quality dudes than I did on any app or as a result of any fix up.

So many of my single girlfriends will pass on things because the chances of them meeting someone there aren’t great. Right, you might not meet your future husband at that pottery class, but you might meet his co-worker, or best friend’s girlfriend, or neighbor. Or you might just make a cool new friend. And who knows what direction that might take you. Or maybe just go BECAUSE IT’S SOMETHING YOU LIKE TO DO, REGARDLESS OF WHO ELSE WILL BE THERE.

I know it’s rough out there, but don’t give up. Don’t give in, just do it differently. Keep shopping, by all means, but until you find the one that you have to have, do some other stuff. Do you.

As for me, turns out I was way off on what I am after. When I shut it down after Tinder Tim and said I was going to spend the down time working on myself, I was just saying it the way people say it (read: I was full of shit and had no intention of doing anything). But while I was busy not dating and not worrying about it, I accidentally ended up working on myself. And as I spend more and more time not just by myself but actually with myself (because, as it turns out, there’s a difference), I am coming to the conclusion that I am after a different kind of happily ever after—one that doesn’t necessarily involve a husband and kids. As I make sense life of post-retirement, one of the few things that I know for sure is this: I don’t want to settle down. At least not yet.

What’s the opposite of settle down? I want to do whatever that is.


5 thoughts on “Shopping For A Little Black Dress

  1. Raina,
    As I have said before, I am very much enjoying reading your posts on a weekly basis. Your insights about dating and being with one’s self are spot-on. I hope love finds you soon 🙂

    1. Regina,I can’t tell you how much I appreciate your kind words and the fact that you “tune in” each week. Speaking of finding love, we have to get our girl date scheduled soon!

  2. Destiny and manifest destiny have a baby. The answer is that in between.

    Things happen when they are supposed to… (read: star alignment, the sufficient amount of pennies in a fountain and having found oneself).

    That being said, let’s be friends again and hang out. Writer chicks should stick together 😉😘

  3. Destiny and manifest destiny have a baby. The answer is always in that in-between.

    Things happen when they are supposed to… (read: star alignment, the sufficient amount of pennies in a fountain, eyelash wishes-after having found oneself).

    That being said, let’s be friends again and hang out. Writer chicks should stick together 😉😘

  4. This is kind of like a quote I love and never understood until during the 4 months that my now husband and I were broken up in the beginning of our relationship…. Love is like a butterfly, the more you chase it, the more it will elude you. But if you turn your attention to other things, it will come and softly sit on your shoulder.
    It’s tough because we are always taught to be go getters and chase your dreams and go after the things you want! So it’s very frustrating when it comes to relationships and these very same ideals are what makes other people run for the high hills. But what you wrote is exactly true, that if you just concentrate on yourself and do the things that make you happy and feel comfortable being single and being you, and fully enjoy the magical wonder that is called life… then that’s usually when love finds you. But the best thing about that kind of pure happiness and self love is that even if love doesn’t come, or maybe comes a few times and doesn’t stay, it doesn’t matter, you know you will still be just fine and live a freakin awesome life 🙂
    I’m so happy you are writing and blogging again, I wish all the best for you Raina!!!

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