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.

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There is Always Someone Prettier

In response to a blog I recently wrote, a man named Mark from Denver wrote to me to share the male perspective. I’m excited to share this inspiring blog with a message that I try to send through this blog, and one that I think all women – single, taken or otherwise – need to be reminded of. It’s even more refreshing to hear it from a single guy. Thanks for contributing, Mark! Check out his blog here, ladies. 

“There is always someone prettier”

I heard this come out of my friends mouth as we were walking down the streets of NYC last week. She had flown in from Hong Kong for work and I was in town visiting my potential place of residence. We met up to hang out and spend a few days together.

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The Guy Who Called Me Undateable (And Why I’ve Never Forgotten It)

I really (really) liked David.

I was a 19-year-old, wide-eyed, excited kid that immensely enjoyed the attention from an older (by um, two years?) guy who wanted to wine-and-dine me. (Mostly from his apartment, since I couldn’t, you know, order a glass without being carded in my quiet, sleepy college town.) He was an engineering major with a big passion to design skyscrapers (and I wanted to live in NYC, it was fate!), and though his room was messy and his shirts smelled like mildew, after two dates, I was pretty much smitten.

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What About Me?

A month ago, I was sitting at a place I didn’t want to be at in Murray hill, drinking wine I didn’t want to drink, waiting on a man I didn’t know if I wanted to date.

I was passing time and nursing my one glass because I didn’t want to leave the place and be forced to sit outside his building where Lucy would die of thirst. Mr. Unexpected had some sort of test that night and Lucy had a grooming appointment the next morning a few blocks from his apartment, so it made sense that I would sleep over… but as I tried my best not to obsess over when he would text that he was out, I wondered what the hell I was doing.

On paper and mostly in person, Mr. Unexpected and I really connected. The sex was great. He made me laugh. He was honest. The chemistry was there but there was also a big ole’ thing missing that I knew, he knew and probably even Lucy knew if we had a way of asking her. I couldn’t put it into words then, but a month later after a weekend of silence to “clear our heads” and “decide what we both wanted,” I found myself sitting across from yet another man who couldn’t give me what I wanted.

But there was one big difference in this mini relationship – and that was me.

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I’m One of NYC’s Most Desirable Singles?

A few weeks ago, I received a message from a lovely woman inviting me to join Rachel Chris, a luxury dating/matchmaking site — and naming me (yes, me!) one of the Most Desirable Singles in NYC. I was actually at work when I received news and immediately turned to my senior editor, partially freaking out to tell her my surprising news. She kindly congratulated me and I proceeded to text basically every person I know. Why? Because I was so stunned — and frankly, flattered — to be part of this selection.

The site finds and picks out active singles in the city, writes a bio about them and has a photoshoot (photos below!) for their exciting feature. Then, Rachel Chris holds great mixers and parties throughout the year, and as part of the nomination, matches you with 20 singles based on what you say is important to you in a mate. In simpler terms: it takes out the online portion of online dating — singles are still listed online (you can see my profile here) but a professional matchmaker curates the dudes best suited for you based on who sends you a message. And then, so you actually stop clicking and actually click in person, there are events you can attend to meet these folks.

I love it. (And though I like this Dr. Heart guy, I’m intrigued to see who I’ll be paired with!)

I was discovered, if you will, by this blog and my constant descriptive and incredibly personal and honest writing that I hope portrays what it’s really like to be a single gal navigating the confusing world of love, especially in a place as robust and interesting at Manhattan. So this is for you, wonderful, dedicated reader who tunes into these pages each and every week (and sometimes every day), to support me and relate to my struggles and my victories. Not only has this blog always been a place for a great venting session, a stress reliever and something I’m proud I created — it has also always been a community of commenters who give great advice and make me feel so not alone on my single-girl-in-the-city adventure.

I hope you’ll check out Rachel Chris — and search out your own matchmaking service wherever you live. (I’ll be sure to report on how it works out for me!)

And because I can’t stand not to share them, here are some fun outtakes from the photoshoot. Thanks again, Rachel Chris — it’s a complete honor to be a desirable NYC single lady!

391297_10100561710639468_49430562_n 483102_10100561710759228_1275954547_n DSC_1288Don’t forget to write a love letter for Valentine’s Day to yourself! It’s Love Addict’s 3rd Year of Valentine’s Day From You to You!!