I always worry when the texting is too good before a first date. It’s almost like some sort of cruel trick from the universe—if you’re really, really connecting with someone via emojis and clever answers to the most basic of questions, the chemistry almost never translates in person.
Case in point: a guy named Charles I went out with a month ago.
I was searching for tights at T.J.Maxx when we started chatting on Tinder. Right from the start, he was an excellent conversationalist and asking the kind of questions you want men to ask: What are you most passionate about? Why did you make the big move from NC? What makes you happy? And best of all, like me, he had a dog—so he totally understood that I needed to head home post-work to walk Lucy before meeting up at a swanky lounge.
A year ago, I published a blog called ‘Dear Boy.’ It was an ode to all of the jerks I went out with that year as a way to dismiss them and let ‘em go. I was amazed when I received so many letters from all over the world of women (and men!) experiencing the same let down.
I don’t know what it is about writing, but it sure does get it out, doesn’t it?
So in honor of releasing all the bad of the year to prepare for a bright, amazing year ahead, I want to encourage you to write Dear Boy letters again! You’re welcome to anonymously submit or use your name (or a fake one).
Just click this link and fill it out. I’ll email you when you it’s published.
To inspire you, here’s one from me:
Dear Boy Who I Though Could Have Really Been Something,
After our marathon date that lasted nearly 48 hours, I was smitten. Our conversation and chemistry was magnetic and I was so impressed with your follow-up. You were handsome and charming, and yet, a little more reserved than I usually go for. I thought stepping outside of my normal dating routine and going for someone who was less the life of the party and more an intellectual with a goofy side would be good for me. But what I didn’t realize is that you weren’t really grown-up yet. You didn’t know how to manage stress. You didn’t know how to balance life, work and love. You didn’t know how to stop being selfish and frankly, you didn’t know how to give a girl an orgasm. I was a little sad when we ended things – at some bar in midtown – but more than anything, I was relieved. I didn’t want another relationship where I did all the work, where I had to put up a big fight and do the wooing. I want someone who can do that all on his own. And I know I’ll find him, and I hope you are one day able to take a deep breath, relax and really let yourself fall for someone. It’ll be a lonely life if you don’t.
With love, Linds
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So here’s the honest truth: I haven’t had sex since July.
I know, I know—you would think for someone who dates as much as I do and is so open about her personal life, I’d be getting a little more nooky. But since I ended that kind-of-relationship with Patrick right after the Fourth of July, I haven’t been laid. Sadly, I haven’t even been touched more than a drunken ass grab outside some crummy bar downtown.
A year ago, I was out with friends when a cute guy started to talk to us. In many ways, he was the type of person I’ve gone out with so many times before: educated, handsome, tall, in banking, a little bit of an asshole and a whole lot of charming. It might have been my frustration with dating at the time or that I saw so many ex-boyfriends in his eyes, peering back at me over his vodka water – but I just wasn’t into it.
He, however, was relentless.
We bantered for a while, but as soon as my friends gave me an exit, I turned away. He stopped me and I smiled, as I calmly said, “Look, you seem great, but I just don’t think I’d want to continue this. I’m trying to be smarter about who I go out with.”
He looked shocked (rightfully so), but he grinned as he replied, “I was about to ask you for your number. But you’re right, I was mainly trying to sleep with you. How long have you been single?”
On my 24th birthday, still hungover from the night before, I stumbled into my favorite pet store downtown and bought a dog. I was a bit heartbroken from my last relationship (yetstill sleeping with him) and I saw a cute clearance puppy in the corner. They say when you meet the right person, you just know (I wouldn’t, since I haven’t), but when I held Lucy for the first time, she fell asleep in my arms and something in me said: buy the d*mn dog.
A few hours later, Lucy and I were sitting on my bedroom floor surrounded by hundreds of dollars worth of dog toys, training pads, a dog bed, treats and food, staring at each other, wondering: Now what?
Once upon an OkCupid message, a dude named Andrew messaged me.
His message was charming and thoughtful, unlike the many (sarcasm intended) ‘Yo baby, wasssssup’ spams I get and frankly never understand because, does anyone respond to that?! Anyway, we did the flirty back and forth text tango for a day or so before he asked for my number. I made him give me a pickup line for it, he went with the cheesiest one, and I smiled at my desk at work when I read it.
Two days later, we were finally setting up our first date when he suggested a well-known, old school Italian joint in the West Village. I had always wanted to go but could never afford it, and it felt really odd accepting such a generous offer from someone I hadn’t technically met. But he was tall and had a great, interesting job and we seemed to like the same things, so I gave in and made an off-hand comment insisting I’d buy him drinks after dinner.
It’s been a while since I’ve been in one of those relationship things. You know, that thing where you have a guy who adores you, who you hang out with all the time, and with whom you have consistent (good) sex? I wouldn’t say it’s changed me for the worse (in fact, I’ve learned a lot about myself, what I want and what I definitely don’t), but being a single gal in NYC for the past three years has made me develop a few slightly irrational fears. Or okay, a lot of them.
But I know I’m not the only one who has nightmares about being attacked in my sleep by the nonexistent cat I don’t own or that my boobs will sag to my knees before I ever have a chance for someone to truly appreciate them. Right?