Another 20-Something Dating Blog

[20somethingdatingblog]

The Roommate

I can't. I don't know where to even begin. It still hurts to think about this. If only things were different. If we were different people. I actually care about him. I'm a fool. I don't know what to do except to let time heal things.

[20somethingdatingblog]

The Platonic BFF

My friends often ask what's going on with my friend Sebastian* and I. We've been friends for over 10 years, he flies cross country to visit me every few months, and we talk on the phone at least weekly. Not to mention we always plan adventures together. And yes, he is very single and quite good looking. We actually look like a cute couple together. But we're such good friends with such an easy-going relationship, it's just fun keeping it this way. We can share a bed without any physical tension and truly enjoy each other's company. No awkwardness - just innocent company. On top of that, he's way too "normal" for me. His lack of issues doesn't interest me at the slightest. However, we'll chat if we're both still single at 35.

[20somethingdatingblog]

The Friend

It's quite obvious that I've been quite self-destructive when it comes to dating. The more unavailable and damaged they are, the more I want them. In the midst of this, I realized that if I was a smart girl, I would lock my friend down. I would be with him. And it would probably be an amazing relationship. Our friendship goes back to the first week of college. We're the type of friends that despite not seeing or talking for a few years, we were able to pick it up where we left off. Not just that, he is the ultimate definition of a catch. Tall, handsome, well educated, successful, confident and nice (in his own way). But throughout our 10+ years of friendship, I've wondered back and forth about my interest in him and vice versa. How is it that we're such good friends? We're similar but also very different. I know he admires me as a person, and for him to not just respect someone, but also admire, that's something. At the same time, do I see him as more than a friend and can I see him as a boyfriend? Would I want him to hold me and kiss me that way? I don't know. I'm scared of finding out because what if the answer is yes, but the feelings aren't mutual? What if we are supposed to be friends and that's it?

[20somethingdatingblog]

I thought wrong

I was bored and up for some excitement. Who better to dish it than the married one? He even had his handcuffs ready when I got there. Before I went he said it makes him feel bad for cheating on his girlfriend. I didn't think much of it. I figured he was manwhoring around, fucking other young girls for fun. What would it matter for him to fuck me? The sex was just as violent as last time, but so much more enjoyable. It was also freeing as there's no implications of it. Just really fun sex. Yes, he slaps me, gags me, handcuffs me, grabs my hair, forces me on my knees and fucks my ass like there's no tomorrow. Kinky stuff I wouldn't be comfortable doing with other people. And his cum... delicious. I asked him later how many other girls he was fucking aside from me. His answer, "none." That means he's really been trying to be loyal to his girlfriend. That changes everything. That leads to guilt. But what do I do the next morning? Deep throat him til he came before going off to work, of course. I'm a fucking mess.

[20somethingdatingblog]

The Tax Attorney

The first guy I had sex with after my divorce was this really boring tax attorney. I didn't think about him til his AOL account got hacked and sent me some spam. Oh yea, he was pretty lame. Big dick but really awful in bed. Even worse out of it. I mean, granted he's a tax attorney and he has an AOL email address, but still, with an apartment by Lincoln Center and having lived in NYC for years, I thought there would be more excitement. But no, he was a snore. A dud. I did once end up at a bakery by his house to see friends and was so scared of running into him.

[20somethingdatingblog]

We Fucked

We actually agreed previously not to fuck. He felt bad cheating on his girlfriend and I didn't want to get tangled up in his web of.. of what exactly? Lies? Dishonesty? Sex addiction?

But after weeks of sexting, of NSFW pictures, including one of his ass and balls, we fucked. I think it was partially because I had fucked another guy. Maybe he wanted to prove something to himself? 

It was rough. It was violent. I bled but I didn't cry. I think he wanted to see me cry, especially since I told him I don't cry. It was wrong on every single level. Especially since afterwards we looked at pictures of his kids and I saw ones of them sleeping like angels on the same bed. And that he had came from having dinner with his girlfriend.

I don't know how I feel about this affair. It's a game for both of us. The scary part of this is that I do think of him as a friend beyond the sex. I'm unguarded about so many facets of my life. My family, my fears, my goals, my ex, my career. It's like because what we're doing is so wrong on so many levels, there's no point in hiding anything from each other. 

As to who I prefer fucking. Let's just say it's Saturday and I crave the other guy's touch and approval right now, not his.

[20somethingdatingblog]

Him

Even though I stayed the night at his place, we didn’t actually fuck. Maybe it was a good thing with the whole divorce and him already having a girlfriend thing. But I was on my period and I don’t fuck with it. As kinky as I can get, period blood is a no go.

It was still one of the best nights I’ve had, sex or no sex. The things he does and wants, it's so damn hot. Plus for some odd reason I can be so honest with him. My answers surprised myself. I blurted out so many things I never thought I'd say. Like why I'm actually so scared of relationships. Plus it was nice that he snores. I found it comforting and soothing.

[20somethingdatingblog]

The First Frenchie

I'm a bit obsessed with French guys. The accent, the swag, everything. Half of the time I can't understand them but I just find it so sexy. The first Frenchie was one of the first guys I met off Tinder. He was/is something of an enigma. Truth to be told I don't remember his name. But he was cute, very cute. And weird, too. As a lover he was alright. Nothing I can actually remember anymore. Except once when he was drunk he texted for a booty call. When I finally agreed and headed over he had passed out. Fucking asshole. I do wonder what his name is though.

[20somethingdatingblog]

Nice view from The Frenchie's new apartment.

[20somethingdatingblog]

The Married One Having An Affair

I've come to realize that I'm attracted to unavailable men. Maybe I'm still scared of relationships, or maybe because I hate wondering whether or not there's something there, but unavailable men work for me. Whether it's a handsome guy just traveling through New York for a great fuck, or the man I'm to describe, I'm drawn to them. This guy told me straight up that he's still married but was divorcing his wife. He was excited to get off the couch of their shared apartment to his own apartment. They have two kids together, a boy and girl, both under 10. He wasn't looking for anything serious, and I actually felt relieved. A day later he spilled more. He started by saying his life was a mess. He actually has a girlfriend and is madly in love with her. But she's married with a kid of her own. They've been seeing each other for two years and rendezvous once a month for what he calls "amazing sex." But to him it's more than that. He wants to marry her, for her to be his children's stepmother and to have a child together with her. And most importantly, both the wife and the girlfriend must not know about me. For some odd reason I'm 100% fine with that. In fact, it makes everything easier because I can't have expectations. I can just enjoy his company for the time being without any grandiose plans of a future. In that way, it's safe. I can't be heartbroken with everything laid out so plainly on the table.

[20somethingdatingblog]

The TV Guy

I don’t know if I actually like-like the TV guy, but I certainly appreciate him in various ways. He’s a huge foodie, he appreciates my smarts and he’s chill but interesting. Plus he’s a creative guy who is also a bit corporate, meaning he’s not just an “artist.” But I don’t know if he digs me and vice versa. If he likes me then I certainly don’t mind seeing more of him. Then again he doesn’t seem that interested. Maybe he’s just polite. I’m beginning to wonder if I’m capable of liking another individual. Or maybe I just want someone to hang out with that I wouldn’t also mind fucking. Who knows. I’m complicated. Or rather, love is complicated until you meet the one

[20somethingdatingblog]

The Cute Finance Guy

Out of all the guys I've met so far, this was the one I liked the most. He was so cute, so chill and had the softest lips ever. I could kiss him for days.

The first date was as normal as any first date goes. We had drinks at a wine bar in West Village, then went off to a dive bar he wanted to check out since he noticed that they had Mrs. Pacman inside. I thought it was adorable that he was into vintage arcade games. We just sat and chatted for a while, both of us extremely tired from a long week, but not wanting to leave. At one point he complimented my perfume. It was Stella by Stella McCartney. I've yet to wear it since I last saw him.

Our second date was not so traditional. It was a semi-hook up for what it was. But he was so damn cute and I was so ready to jump him anyways. We watched baseball at his place, a very cute apartment right in the heart of West Village. I liked being able to see the crowds without being in the crowd. 

Then two days later, he stopped texting. It was a bummer since he had said he would join me at a fundraiser party and I was excited to have him see me dressed up a bit more than I would on a casual date. Alas, I'm sure another pretty girl got to his heart. Or perhaps his ex. I don't know.

What made me like him the most? All the little things I supposed. I liked his chill mannerism and the way he talked. I liked how ambitious he was with his career and how he seemed like he had a good head on his shoulders. Plus I thought it was so coincidental that my new apartment was just a few blocks from where he grew up and that I studied what his dad teaches in college.

And those lips. Seriously, I've yet to kiss a guy with lips as soft as his. Sometimes my fingers itch to text him, despite my habit of deleting guys who either stop texting or who I don't care to text. I know it won't do any good, so sometimes I imagine running into him when I'm having a cute day. Alas, a girl can fantasize, right?

[20somethingdatingblog]

The Super Villain Guy

Things never turn out well when upon meeting a guy, the first thought you have is, "Wow, he really looks like a cartoon drawing of a super villain."

But that really was my first thought. He had a strong masculine jawline, high cheekbones and deep sunken eye sockets. His eyes were the villainiest of it all. They were an electric green with blue irises. Just super intense and bright and just captivating.

But he turned out to be an affable guy, easy to talk to and quite interesting. He was a bit on the snobby side, but then again, that's pretty common in New York. I wouldn't categorize him as a douche, but he's clearly worked hard to enjoy fun hobbies like traveling, biking, etc. Apparently he also likes fancy cars.

I like those things, too, but I'm just way too broke to partake in them. He probably found me too low brow for his taste. In any case, I did ask him if he was interested in dinner the following week and got rejected. In fact, his text reply was so formal and polite, it was worse than a flat out rejection. He wrote, "Hi 20somethingdatingblogauthor. Thank you but I'm working late all week. Maybe next week?"

So take-home lesson: if you think a funny/negative thoughts about a guy, chances are it's NOT going to happen. Apparently nicknaming him Super Villain guy doesn't help.

[20somethingdatingblog]

The Ross

When it comes to online dating, it seems like each site and app has it's own share of men. With E-Harmony it's about finding that one true Match to marry and OKCupid is more about hookups. Tinder is somewhat different as there are no profiles - just 5 pictures from your Facebook. If you both mutually like each other, you can start chatting.

The beauty of it is that you can make it anyway you want. Yes, many people are on there looking for simple hook ups, but there are some just looking to meet people. I use it for both.

I went on with a mind to look for a cute hookup the other day. I thought about texting the Frenchie (another hookup I found on Tinder), but I was in the mood for an unpretentious guy without a European accent. It was after Fashion Week and I had it with pretentious people and European accents!

Saw this somewhat cute, all-American seeming guy's profile and clicked on the heart. Et voila, a match! Quickly sent him a message and pretty soon we exchanged numbers and escalated our texts to very very flirty texts and sexts.

It was easy going, light-hearted and drama-free. Then he mentioned that he smoked weed. I am always on the hunt for a fun smoke/fuck buddy, so in essence, that sealed my decision. I will head on over and smoke out with him then fuck. At worst it'll be a one-night stand. At best, a long-term fuck buddy that I could text whenever I needed a tune up.

So I head on over and he's just as I imagined. An unpretentious, easy-going All-American-esque type of guy. We chatted, he rolled a blunt, smoked up... and I got up and somehow stumbled next to him. Before I knew it his mouth was on mine and his hands were all over me. Within seconds my panties were gone, my wrap dress unwrapped, his mouth was on my nipples and his fingers were deep between my legs.

And it felt so damn good. 

I stopped to take his clothes off, but he just froze. He looked at me and uttered the words, "I can't."

For split second I felt so vulnerable, so exposed and so unwanted.Here I am, my legs wide opened, ready to fuck and suddenly the guy says he can't? Am I hideous or something?

Then he continued. "I keep thinking about my ex."

Alas, that illusion of a drama-free, mess-free, easy, no bullshit hookup dissipated.

Turns out they were on a break. Yes, a damn break like Rachel and Ross. And I was the copy girl.

I covered myself up, asked him some more basic questions. And empathized. 

Although he didn't want to talk about the subject, from what I gathered, it's a very complicated relationship. He's paranoid that she's still keeping tabs on him, and in a moment of weakness, he wanted to see what was out there. What better way to check out what is literally within miles of you than Tinder? 

With me coming in looking for a simple hook up, I can see how to a guy in the middle of a stressful relationship, that would be enticing. It's the antithesis of everything he's going through with his girlfriend. Plus I'm sure I'm cuter (duh).

Except for that moment of vulnerability when he pulled away, it wasn't all that awful. Obviously he didn't end up being the hook up buddy I was looking for, but in other ways I enjoyed myself. He was interesting and easy to talk to. After a little while he forgot himself and started flirting innocently again. 

I do hope him the best. He's not a bad guy, just a confused guy after all.

[20somethingdatingblog]

The Me

Unlike most 20-something single girls living in New York City, I didn't start dating until I was 27. It's not like I was some virgin that wasn't interested in dating. Not at all! I was just married to my high school sweetheart until I was 25. For my 26th birthday I got a watch and a divorce - huzzah!

It took a year to heal, to stop blaming myself for a crumbling relationship, and to stop seeing all men as lying, cheating, cowardly bastards. Plus I needed to stop looking for my next husband. When you've never been out of a relationship, it's really hard to not want to find yourself back in a relationship.

Plus after the divorce, I moved home for a bit and spent all of my time with my family. It's very hard to get action while hanging out with your mom, as awesome as she is. I also decided to move across the country to NYC, which took a while to acclimate.

But two years later I'm finally ready to put myself out there. And you know what, dating for the first time as a late 20-something girl in NYC in 2013 is somewhat weird. Where do you meet men while juggling work and an aversion to bars in NYC? If guessed online, ding ding ding, you're right!

From the tried-and-true of many like Match and OKCupid to the newer apps like Coffee Meets Bagel (which is a dud - I've never even chatted with anyone on that app) and Tinder, here are my stories of the various men I've encountered.

Note - I'm not writing in any sort of chronological order.