9 Totally Normal Breakdowns I’ve Had About Being Single

From my Facebook page looking in, I seem like I pretty much have it together.

I have a job that I really love, I signed with an agent this year to turn my blog into a book, I live in one of the trendiest neighborhoods in New York City, and I’m lucky that I’m a good enough saver that I make it overseas a couple times a year for a vacation.

I’ve been pretty d*mn successful (knock on wood) so far in my 20s, but the one thing I’ve yet to master is dating.

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Without Any Apologies

Sitting across from Dr. Heart at my favorite Thai place near NYU on Saturday night, I caught myself sneaking a smile at him when he wasn’t watching. The restaurant, though not really known for their food but rather for the good cocktails and candlelit ambiance  is perfect for quiet conversation and a hearty, boozy meal. Which is exactly why I picked it for dinner, and because it was right near our next stop: Webster Hall to see Lindsay Sterling.

He caught me looking at him and asked about my intentional studying and if I had drawn any conclusions. I flirted back, telling him I would give my full assessment by the end of the night. This is how our canter is — quick and playful, then serious and deep. It’s really the best kind of start to something that could ultimately be something: half-fun, half-intense. He picked up and kissed my hand, called me gorgeous and went back to his sake. It was the start of a great evening that had followed a great day of sledding in Central Park’s beautiful blizzard and eating pancakes at a cheap diner near my apartment.

We were going to build a snowman until Dr. Heart took a freezing fall into a hidden puddle at the end of a hill, leaving him soaked and very cold and leaving me laughing the whole 10 blocks home. We walked hand-in-hand while admiring the snow and popping a kiss here, racing each other up steps there. I had enjoyed every little, single detail of that day and our meal so far except for one thing.

His hat.

It seems like a petty thing really, especially now as I sit down to write this blog. Though Dr. Heart normally has a good sense of style, for whatever reason, he selected a brown hat to prance around town in — and well, I really didn’t like it. So while I was admiring his devilish good looks (as my grandmother would say), I was also secretly wishing that brown paper-boy looking thing on his head would have stayed at my apartment. And Lucy would have somehow snagged it and you know, do her dog destroying dance.

But no, it was there in our cozy little corner of the restaurant and it was there again, in our cozy seated VIP table at the concert. While we were sipping on Stella and watching the crazy light display below, he let me know he was going to the bathroom to take off the hat because he was hot. I tried not to smile too eagerly, but I’m sure he could detect me grin from the other side of the hall where he was headed. At the end of an amazing set, we started to layer on the half-dozen winter pieces that make New York City bearable in February, and as I reached for my gloves, I noticed that hat hanging out on top of my purse. I offered to hold onto it for him — yes, probably with grim intentions floating in my head — and as he went to retrieve it, I must have frowned.

You don’t like this hat, do you? He asked as a sly smile wrapped up his cheek. Surely blushing from pure guilt, I shook my head and confessed, I kind of hate it. He pulled me closer to him, nibbled on my forehead and laughed, It’s okay, you know, to say how you feel. In fact, I want you to.

There are a lot of things about my experiences with Dr. Heart that are very (very!) different from my relationship with Mr. Possibility, and for me, the biggest one isn’t exactly the doctor himself, but how I at like myself around him. Now, a hat isn’t exactly a deal-breaker (though if you saw it, you may disagree. Ugh), but other things could be for me. And while I really am starting to care about Dr. Heart, I also have no problem being very honest not only about what’s going on in my head, but also about what’s important to me.

In other words, I’m finally speaking for myself in a relationship instead of catering to the every wish,  desire and demand of the man I’m wooing. Instead — I’m letting him woo me, first.

It really doesn’t sound like such a novel concept and really, it’s not. But for me — the girl who wanted to be the dreamiest dream girl that ever walked the streets of Manhattan — letting go of being perfect and being strong enough to show someone what I really think, what I really want and what I really need is a huge step in the right direction.

In the past, I needed to hold onto a guy so closely that I wouldn’t dare test his feelings by spending time apart from him. But with Dr. Heart, when I need a “me” night because I’m stressed from work and aching from pushing myself too far running, I let him know and lets me have my space (and provides a bottle of wine, just for me, to relax). I used to agree with ideas or let behaviors that I knew could turn into bigger annoyances down the road (ahem, not cleaning up after oneself) brush off my shoulder instead of addressing them. And yet, with Dr. Heart — we aren’t afraid to sweetly explain to each other what’s bothering us — even if it’s as simple as, Hey, those boots covered in snow, don’t put those in my doorway. I have always tried to make a guy feel extremely comfortable by making sure everything was just-right: my look, my apartment, my manners — but now, I don’t always fetch water for Dr. Heart (he knows where the Brita lives), I don’t have to wear makeup 24/7 (he does need to know what I look like without it) and if everything isn’t in it’s assigned place in my bedroom, well, then it’s not (it might be cleaner the next time he comes over).

Sometimes, being this at ease and being able to really just let myself be myself and speak for myself makes me feel like I’m not trying that hard. And you know what? I’m not. I’m still sweet and playful. I do little things like leaving surprise notes in pockets and Thinking of you text messages. I still cook dinners and sometimes, come straight home to cuddle in bed. I’m still supportive and understanding, kind to the bottom of my heart and yes, selfish from time to time. I’m not always in the best of moods or always in the mood but I still a girl worth dating.

Because that’s just who I am — and maybe, showing all of those characteristics will lead to a relationship where it’s fine to be… me. Without any apologies, at all.

(And hopefully, without Dr. Heart’s hat, too.)

Only TWO more days left to submit your Valentine!!!! Get to it — you deserve a love letter from yourself :)