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Why Not Caring About My Dating Life Has Made It So Much Better

On a trip back home, I recently connected with my high school boyfriend. He was that guy that so many have—the sweet, loyal and fun first relationship that’s the equivalent of a training bra: comfortable and exciting, but not something that can last forever. I broke up with him—quite dramatically—within my first few days of college because I wanted to experience all that the single life could offer me. I had been tied down most of high school, so why not explore?

It was a rough breakup and we stayed out of contact for the better part of the last nearly nine years, but with one Facebook message, we agreed to meet for our first legal drink together. I don’t have a car anymore — thanks NYC transit!— so just like he did all of those years ago, he stopped by my house to pick me up. As he walked up the stairs, my heart started racing with all of those butterflies that I felt when we first kissed, when we first had sex, when he told me he loved me. Continue reading →

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What Dating is Like In Every Year Of Your 20s

There’s no doubt that some things get better with age — wine, cheese, sex. But there are other things that change so much year-by-year, that it’s hard to look back at where you once were. And if you’ve been trying to find something shiny in a pool of lackluster dates, then you likely know that dating is different in your early 20s than it is in your late 20s.

Go ahead now and ask for forgiveness for what you tolerated when you were 21, because the approaching-30 you would shake your head at what once impressed you. The nice part about being single for multiple years — is that you figure out more and more what you want, what you don’t and what you’re willing to compromise on. And in some very powerful, awesome, ways, you also learn how to care less about how it all goes and expect more out of yourself and your future partner.

In case you need a good belly laugh or you a reminder of how far you’ve come — or where you’re headed — here’s what dating is really like in your 20s. Naturally, in GIFs, because those are fun through the entire decade.

Age 20: I So Don’t Need A Boyfriend/Girlfriend.

Being single in college is so fun! There are so many parties, so many eligible people, I don’t want to settle down. I have time. I mean, it’s not like I’m 25 or something.

Continue reading →

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I’m Really Burnt Out of Dating… But That’s a Good Thing

After 10 days of heavy antibiotics (thanks to an impromptu trip the ER), when my friends suggested margaritas on a Friday night, I happily obliged. We went through our usual catching-up work — craziness, what exercise class we’re planning to go to, the awesome event we should all sign-up for — and then we turned to the most entertaining topic: dating.

The two ladies I happened to be snacking guac and downing tequila flights with that evening were single like me. And though we’re all at varying levels of singleness, we all settled on one little fact: it’s hard. But while they stayed mostly optimistic about it and at least somewhat excited about the prospect of new dates (that could hopefully, turn into more than happy hour partners) — I was on an entirely opposite end of the spectrum. I’m tired of dating. Continue reading →

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5 Things I’m No Longer Apologizing For in Dating

Subconsciously or consciously, how often do you find yourself apologizing? You slightly bump into a stranger and you mutter a ‘sorry.’ A co-worker interrupts you, and yet, you find yourself stammering to apologize first. Or, perhaps just as frequently, you find yourself talking about a bad date and when you feel like your friend has had enough, you quickly quiet yourself, say you’re ‘sorry for venting’ and move on.

It’s a habit that many women (and men) are guilty of and one that’s difficult to break. Continuously shaming yourself doesn’t help build your confidence, and oftentimes, can be unattractive to possible boyfriends or girlfriends who are looking for a partner, not someone who can’t hold their own. While it might not feel like it’s in your nature to stand up, speak up and be proud of your opinions, convictions and emotions, chances are, your date will be impressed with your willingness to be open, vulnerable and honest about how you think and feel.

In my past several years of being single and going on (way too many) dates, it’s taken me a lot of time (and wine) to finally figure out how to be brave enough to be myself. And while I haven’t met that right person yet, I have learned how to have courage and to stop apologizing for these things:

I’m not sorry that I expect you to communicate.
Online dating can wear on anyone – there’s constant back-and-forth exchanges, but very little face-to-face time to genuinely get to know someone. There’s also many messages to weed through that can be boring, rude or just plain ridiculous. For a while, I would always step up and speed up the conversation myself, oftentime apologizing for being so forward. The funny thing? Men never cared that I carried the conversation, but I did. In a future partner, I really want someone who is not only a talker, but that can ask interesting questions, have meaningful decisions and hopefully, teach me a thing or two from his own wealth of wisdom. I’m not sorry that I want a communicator – I’m sorry I ever thought I could settle for less than that. Continue reading →

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Here’s What a Trip to the ER Taught Me About Being Single

I’ve been single for the better part of my adult life, and though I try my best not to sweat it (and remind myself that I’m only 26 and my ovaries have time), I, like many people, have certain fears about being single. While I’ve never worried that I could die alone in my apartment and go for days unnoticed (my dog and amazing roommates would know in a hot minute), I’ve always wondered just how much that emergency contact would matter if I ever actually needed medical assistance.

Last week, I got the unfortunate opportunity to find out. Continue reading →