Dating Rollercoaster


Dating is exhausting. It’s a roller coaster with a series of highs and lows. We all have different approaches, different schools of thought. With online dating, some are able to take on a rapid succession of dates, which can make the ride less remarkable. Others are prone to invest heavily in each new date: a big climb, which can result in a thundering drop.

At the end of last weekend, I began chatting up a Tinder match. She was my usual kryptonite: blonde, impeccably dressed, in fashion. After tough one-word responses from her, I was able to get her to open up and had an evening of rapid-fire exchanges on chat. We made plans for Wednesday night. During our conversations, she mentioned that she had met someone who was “really really nice and well-mannered” through the app. What was the problem? “He was remarkably short.” She ended up asking me if I was over 5’4” so she was “prepared” and I am. But not by much… I hoped she was smaller.

A few hours before the date, I checked in on Hinge and lo and behold, there she was. 5’4” – damn. As you know, height tends to be a theme for short guys. I’ve been a bit formulaic with dating and went to the usual place. Mental note: switch it up! As I saw her entering, I saw them: the heels. Fashion girls wear heels no matter the conditions; they love their stilettos and only having children will eclipse this love. Do not get between her and the Louboutins. With heels on, she was taller than me. Probably a disappointment, but I soldiered on. This “go-to place” is always loud and we couldn’t hear each other so I had to re-arrange the chairs to the entertainment of our neighbors, while she made small talk with a neighbor drinking alone. When we switched, the neighbor was stood up by her friend, but wasn’t sure because she left her phone at home. The two of them would end up in a highly intelligent conversation about environmental law and energy. It was impressive and I had nothing to contribute. Not a good look.

When the neighbor left, I finally had my chance and I went after it. The charm offensive generally works, but at this point, the climb was high. She was laughing, talking, but stopped drinking after one, then declined my invitation to grab a bite since she ate earlier and had to walk her dog. Ouch. I told her we might eat after, so I didn’t really believe that one. And that was it. I walked her to a cab, she half-expected me to jump in with her and drop her off, but I needed the walk. She said something about me being really cool and speaking soon, but it was like being given a parting gift. The irony. Ladies, when you hurriedly rush out, it doesn’t make us want you more. Sometimes it does. Sometimes, it just makes us feel like you wanted to get the F out of Dodge. I had zero intentions of messaging her.

The next night, I was out drinking with friends and recapping this fiasco. I realized I’ve come to terms with the idea of winning and losing. The date with Fashion Girl was a loss. The girl I really wanted was the Nurse. As I was showing my friends pics of Fashion Girl, they were commenting that she was beautiful and pangs of regret began to trickle in. And within the hour, she texted me to decline my invite for any plans that weekend (including Valentine’s Day). Naturally, this triggered me to text Fashion Girl something. Dumb. Dumb dumb dumb. The loss just became a blowout.

And the dating roller coaster continues. Wait on the long winding lines, strap yourself in, make the big climb, take big drops, take small drops, do it. It can be The Cyclone, it can be the Great American Scream Machine. Pick one that suits your style and hop on. Just don’t forget to get off when you need a little break. Because we all end up needing a break until we meet someone who makes us want to stay on.

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Expectations and Priorities

changed priorites

The last time I hung out with the nurse, she revealed a glimpse into the uncertainty she’s been feeling. The focus of these emotions was not about her recent break-up, but it seemed to be the catalyst for a reassessment of the path she is walking. I have been going through a similar thing and it was in this moment that it dawned on me. Maybe now is not the time to find this relationship either.

At work, I recently had my review and it was fine. My team embarked on a Super Bowl campaign and as clients, executives, and colleagues raved about it, I just sat there thinking: I hate this shit. I need more out of work. I also need a higher earning potential. Fortunately, a career shift can easily happen from where I am and I just need to refine an existing skill set that is not overly crowded. Thus, my attentions will focus more on this transition, particularly an intensive 10-week class. Dating will be less of a priority.

I’ve sent my last message to the MILF. Coincidentally, she and the nurse have the same birthday. She shared a gift to herself that she worked on, which was a music video to Tila Tequila’s “I Love U.” This is a terrible song and I can’t believe she chose it, but even worse is the video about being single and the barrage of scenes that lend insight into the challenges of modern day dating. It largely focuses on the fallacy of the Disney fairy tale, but also confesses that women (including herself) are crazy. I believe she is now going to focus less on her blog, less on her erotic vampire fiction, and turn to webisodes about dating. Personally for me, she is too all over the place. I’m sure she’s a great mother, but she’s adding aspiring video producer to aspiring writer and aspiring sadomasochist. On a shallow level, she’s got more jelly than I care for and even the prospect of what sounds like intense mind-blowing sex is not enough for me to stay on the roller coaster.

I wrote back: “That’s some video you’ve got there…”
She responded: “I’m glad you liked it!”

It’ll be interesting to see her continued creative output. She seems to move from one thing to another, but doesn’t stick to it long enough to actually meet her aspirations to make it on a professional level. Either that or she is a bit out of touch with reality. It’s a shame because she does have vision and talent, not just enough self-criticism to strive for a higher level.

We are overwhelmed with messages. Stories in film and literature hint that you and your partner make one, a whole. Don’t fall for Jerry Maguire’s line “you complete me.” You complete you. In my ideal relationship, I hope to give of myself. I don’t need to be completed. I want to give some of me and take some of you. Like the MILF, we all have something great to share. But the question that the nurse poses is: are we ready to share? The uncertainties and lack of satisfaction in other areas of our lives will pervade our personal lives. Because when you share, you give it all. Make sure you’re whole when you do, otherwise you find yourself with nothing.

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Rejection Backlash


Rejection is brutal. It brings out insecurities that you’re never fully conscious of and projects them like a Viewmaster 3D: whenever you blink, another one appears. This and the following week at work is all Super Bowl. The city is about to light up: it’s never hosted the big game before. With the very real possibility that I would disappear in work, I tried to see the Australian again. We made tentative plans, they fell through on her end, but I just offered other times – then suddenly I receive a message with my favorite words.

“I’m not ready for dating…”
“… not quite over my ex…”
“… really nice guy.”

Lingering moments of disappointment came over me, but all in all, I didn’t feel so bad. The rejection and idea of losing was the dominant emotion. It was a broken recording of the same song that came from the nurse. Something must be wrong with me. And there it began: the fog of insecurity crept in and I was analyzing every little detail of our dates, cross-referencing them with my dates with the nurse.

I came to two conclusions. First, our last make-out session was a pail of cold water on her head: I am shorter than her. Second: I’m too intense. In the week and a half we knew each other, we went out three times and were planning for a fourth in two weeks. Meet impatience, my major flaw. I was driving it forward too fast because I would be out of sight and out of mind for a while. Unlike the nurse however, it wasn’t because I couldn’t wait to see her again. This was me trying to get closer before the bustle of life undoes all the good work I’ve done. It did exactly that.

Later in the week, I did see the nurse. After plans the week before fell through, I met up with her and two of her girl friends. It had been two months. You know you’re hooked when you’re sitting at a wine bar hanging with the ladies. I did my best to win her two friends over and finally gave her the book. We didn’t kiss at the end of the night (she was staying with her friend), but her friend invited me up and I joined them. I entered, used the bathroom, then promptly left. At the door, she said she was going right to bed, her friend was heating up food, I had work the next day… and the insecurities set in. During drinks, she was texting away and looking for responses on her phone. This is not how she is with my messages. I get responses 24-hours later. That was when the fog set in.

She texted me quickly after I left telling me she opened the gift and how interesting it seems. I wasn’t sure if she read my note. The next day I knew she read my note when she said the gift was really sweet, while also updating me that the last minute plans we tentatively made were probably not happening. She texted me to clear up why she wasn’t feeling up for it and cancelled later in the evening. If it weren’t for that, it would be the Department of Homeland Insecurity in here. But it comes and goes: Did I make the right move leaving the way I did? Am I being too pushy trying to see her again the next day (even though she invited the group, then asked me what I was doing)? I have no clue. I know she’s not in a mindset for dating, but likes me and we’ll see each other as it happens. So play it cool – this is after all, what I do best and what I do worst. Play it cool to the point where I convince everyone that I don’t give a shit. Throw in her upcoming birthday (either this week or next) and I can easily see myself making that some sort of deadline to get closer. Impatient bastard can easily make a mess of this.

Rejection is a bitch. Don’t let it get to you. It will unravel you in a domino effect of negative emotions. Take a moment to stop and see what’s really happening. There is someone who you really like who is also really into you. If it’s right, it’s simple. You don’t need to figure everything out right now. There are no deadlines. See each other. Enjoy each other.

I gotta follow my own advice.

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Best Laid Plans


They say timing is everything. They also say patience is a virtue. They’re right. Dating is tough. Dating in New York is mission impossible. We who reside here and have come to call this place home, are the most impatient people on the planet. Whether or not you were born and raised, or have just lived here for a summer, we expect everything to happen quickly. Then we begin to think if we’re not living in a state of hustle and bustle, we’re not being New Yorkers. Let me tell you: my best friends and I are the real deal New Yorkers, born, raised, and have spent over 30 years of our lives here. They are more “New York” than me and they’ve gotten the hell out of here. Defining New Yorker is a whole nother story. The point is: are we creating social chaos for ourselves because we live here? And is that chaos and its mentality, getting in the way of the thing we want the most?

I’ve seen the Australian two more times, which is pretty intense considering we only met a week and a half ago. It’s quite simple: we like each other, have a good time together, and she has an air about her that I dig. I would say something about chemistry, but I get along with everyone in early stages – I can make chemistry happen. It’s in the later stages when things fall apart. She has one of those bustling schedules. We’ve had dinner twice again, but there’s always an impromptu air about them. The second date, we made plans for dinner since the first one had a few snafus. She didn’t feel well, asked to make dinner tentative, and scaled down to drinks. We ended up having dinner exactly as planned, except I had to cancel the reservation and was slightly thrown off. That night ended with a soft kiss on the lips. For the third date, we made plans to spend the day together, but a few days before, she cancelled because she had other things to do all weekend. We ended up meeting up after a work function. We had a drink, then went to grab a bite. At her door, we had a make-out session and I suggested meeting up again pretty quickly to which she hasn’t necessarily confirmed. Most likely we’ll meet up, but I won’t have anything planned. The problem here is that I like to plan and prepare a good time out. A guy likes to sweep a girl off her feet. We’ve had very basic dates, which is fine because it’s cheaper for me. I’m not reading into the nonchalant attitude she possibly has regarding plans yet. It’s a loss for both of us. And further, I think the more I invest of myself in terms of time and thought, the more I am invested in the potential of that relationship.

Meanwhile, the nurse texted me back from a message I sent after the Australian canceled our day trip. Was it retaliatory? Yes. When you get canceled on, a feeling of rejection hits you and you act impulsively. Even though I’m very focused on dating one girl at a time, I don’t feel this one has run its course to completion. And for someone who I liked as much as her – one who I saw so much potential with, I wanted that wrapped up in a neat bow. To update: we both have told each other we really like each other already. Her problem is she has no idea what’s going on in her life and is not ready to date. She tried with me and was pretty hard to deal with (just in communicating and planning). She’s still reeling from a break-up she initiated in October, has been living at home with her parents, and apparently is considering moving. We wanted to see each other, so we made plans. I didn’t know what to expect, but whatever is between us would probably take over that night. The one thing I wanted to do was give her a book.

I bought her Tiny Beautiful Things to help her make sense of her own life through the crazy things that happen to other people. But there were also things I wanted to say. On our first date, she talked about not knowing what she’s doing next, the things that may make her stay – maybe some guy. I basically tell her I’m that guy in my note. It’s subtle. Nothing crazy, but it’s a clear gesture. The gift is still in my briefcase unwrapped. On the day of our date, she canceled because her dog had an emergency visit to the vet. She tried to push our date back for the following week, but I couldn’t make any commitments because of work.

In romance, I think there are these brief fleeting moments. They are ours to take when they arise. The problem with is that we’re often so caught up in our own lives – the life where we, our friends, and careers are at the center – that we never create the situations where these fleeting moments spark to life.

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You Must Be This Tall

Rollercoaster heightAs a child, the “You Must Be This Tall to Ride” sign kept me from the thrill of roller coasters. At school, lining up by size automatically meant I led the class in. As you grow older, it becomes less of an influence in your life, but every short guy is lying to you if he didn’t wish genetics were kinder and spared him five, even three, more inches in height. One of the telling features (or lack of) on Tinder is it is height-blind. Many women do offer it up in their profile. Fair enough – it’s great to be upfront. Other sites like OKCupid ask for this, which poses insight into the expectations or the specifications those users require. For me, it’s telling that I meet more women through Tinder than OKC. Could it be that the women on OKC are looking for too much of an ideal man? Or could it be that the ladies of Tinder are more willing to simply find out?

As with every date on Tinder, I worried last night about the height of my date. Is she taller than me? Aside from her being lean and slender, there was no indication of scale. My obsessive side took over and found her on Instagram through our mutual friends. A couple of photos showed she was taller than men. I am normally the shortest guy in any crew. Not a good sign. Are we talking Tom and Nicole or Attack of the 60 foot woman? I brushed it off and got to chatting, which erupted in streams of messages right after Christmas. She had family in and would be away for New Year’s, but we set up plans to meet as soon as she was able. As the date neared, I began to stress a bit more even questioning why I didn’t cancel. Stop being neurotic. I was forgetting who I was. Nothing intimidates me. Maybe she had short friends.

From our messages, she told me she was Australian, which made her more appealing. Accents. I had to step up. Literally. I threw on my “tall shoes” and focused on my posture. Let it glow. Let it glow. I was sitting at a table when she came in and I stood up to greet her. Damn, she did have a few inches on me. I sat back down right away before the facts became cold and hard. What was her shoe game? Heels? How high? It was too dark. She immediately asked how my week has been. Work has been crazier than normal and the height anxiety broke the dam. I revealed a man who seemed to be coming undone. This was going to be a long (or very short) date. Her relaxing air brought us to a point where we were laughing about my professional situation, then it was her turn. Turns out she hates her job too. At that point, we resolved to never talk about work. A second round came as we continued to enjoy each other’s company, so I suggested we grab a bite down the block.

Here we go. May as well line up back to back and stack up. I felt like I was in 5th grade again. We couldn’t teleport to the restaurant. Yup, she’s about two to three inches taller. As we walked, I saw that she had puppy heels on. So two inches (I just wikipedia-d that). We told each other’s stories over dinner and kept talking after paying the bill while our waitress gave us telling glances that she wanted to get out of there. There was an embarrassing moment when we she had to give me money because they only take AMEX, which I left at home and didn’t have enough cash. Fortunately, she only had to drop about twenty dollars. I was mortified. We began walking to find her a cab when she noticed a new restaurant, so we went in for a drink. More chill comfortable conversation like we didn’t just meet a few hours ago.

I’ve been on many dates in my life. Only twice have I not kissed at the end of the night. The other one was recently with the nurse. Upon exiting, a cab was immediately there. She made the move for a kiss on the cheek and I had nothing. There were bystanders and I wasn’t ready to take a Heisman (hand to the face). I asked if she wanted to go out again and she said “sure.”

By the time I got home (10 minutes), I was rattled enough: her response wasn’t convincing enough for me. Or I had enough drinks that kept me frozen at the goodbye and magnified the day’s insecurities. I shot her a text apologizing for the bill fiasco. She responded charmingly and I asked her out on a specific day. She couldn’t, but offered up two other days. We set up date two, then said our good nights.

Height does matter. For those on the short end, it can play games with your mind. You can let it dwarf you or it can make your personality larger. I never thought I would have an issue with dating someone taller, however I assumed the taller of the opposite sex felt the same way. Dating taller women was a high school thing – done when your world was smaller, when you didn’t have the catalogue of options provided by online dating. After last night, my view has changed. There are far too many factors at play to let it all boil down to a single deal breaker. It all depends on the expectations/specifications/limitations you set forth and your willingness to reach higher.

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New Year’s Resolution: Game Over

Super Mario 1 WinI’ve never had a New Year’s resolution. This year I’m finally taking one on: do not play the game. This beautiful game we play is some times called love, but it’s merely the battle for the upper hand. Entering any prospective relationship in its formative stages, we want to go in knowing we have the upper hand. It’s the reasons why our friends tell us not to text or call, why we wait x number of days, and stalk people’s Facebook and Instagram. We want to know that they are into us as we are into them.

This recent snow has led to thoughts that resulted in this resolution. The last time I had sex (which has been almost three weeks! and coincidentally the last time it snowed) really led me to this. I met an advisor on Tinder who, after off-and-on messaging, finally took up my offer of meeting. After a few messages, she asked me to come over that night for dinner. She was watching a kitten, so we would cook or order. Immediately, this sounded like straight-up strange ass. Or a trap planted by a serial killer. I found myself at this woman’s house shared by two roommates. It was a dark brownstone on a dark street with unattended mail notices on the door. This could very well be home to a serial killer – or just some girls in their twenties. She greeted me at the door, tiny unclawed kitten in hand. Halloween cut-outs were still hanging, Christmas lights were up, and Hannukah decoration everywhere. On the coffee table, large piles of fake coins revealed a big game of dreidel. In this room of holidays and antique furniture, I wondered if bodies were piled up in the basement. I went forward with my adventure: played with the kitten, ordered food, and learned how to play dreidel.

How did I end up here in the first place? On her Tinder profile, her face shots revealed a pretty girl with a nice body. Our first series of messages waned and the chat stopped. Like a dog, I revisited it when I saw a new pic: her dressed as Bunny Lebowski (her friends were the rest of the cast). Fun, great taste in movies, and a bikini photo. In reality, her head shots were well-angled with an expression (think how/why people do duck face) that hid her strong facial features.

The roommates returned from their plans before the food got there. We ended up all sitting around (three female roommates, a boyfriend, and me) sharing food, drink, and smoke. As I got drunker and higher, the realities started settling in: I was attracted to one of her roommates and my host was annoying and more than zany. Her heavy use of Yiddish catch phrases (oy vey) went from unique to irritating. She snapped at both of us as we talked and traded looks across the table. The most telling moment was when my date was petting the kitty and her roommate took it off her hands to do the cuddling. Metaphors. She finally retrieved it and started to dance with it, which meant shaking the poor thing wildly. They warned that it’s probably not a good idea to do that. I immediately thought of her shaking her newborn to death.

I discreetly called a taxi through Uber. When the car came. I announced my departure and awkwardly waved goodbye to them as I sidled towards the door. The boyfriend shook my hand: I believe because he hoped I would come back and have a partner in his little situation. The teacher walked me to the door and I stepped out into the hallway out of their sight, so she could give me a hug. As we hugged, we began making it, which quickly led to aggressive groping. It stopped when I began to try to pet her kitten and I made my way out. Part of me wondered if I just missed an opportunity for an awesome one-night stand. In other words, did I just lose?

I resolved not to call her since deep down I had no long-term vision for us. But the self-loathing had grown as the weekend approached and I wanted to win this game. I had to be sure, so date number two. I went to a friend’s party early, met her for dinner where her strange mannerisms continued in full show, then we ended up at my place. We were making out, then the clothes came off. Incredible body. We ended up having sex after major foreplay efforts on my part, and she left after a few hours. I woke up the next day reviewing the date. More importantly, collecting my thoughts since I was a little tipsy after my friend’s party. First, I was thinking about the nurse during dinner. Second, I was thinking how irritating her mannerisms and personality were. My base instincts took over as the night progressed: I wanted the win. Aside from a few text messages, I have not made any attempts to see her since. It was an empty win and it only makes me feel that there is more negative energy stacked against me. After a week or so, the feelings of guilt and greater self-loathing are the only things that remain.

The reality of my situation is that this is no longer a game. This is life. I believe there are karmic forces at play. I hope fewer people will be hurt, while more people, especially me, will be truly happy.

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Taking Flight

Family SignWalking downstairs to the basement level of Duane Reade where the dental care section is, I was promptly greeted by the greeting card aisle. Valentine’s Day. For my fellow singles out there who just survived the romantic pressure of the holidays, they’re coming harder with the full Valentine’s assault. We haven’t even had the chance to experience our regrettable New Year’s Eve hook-up; Cupid and his army of red hearts have already descended upon us.

If you’re a thirty-something male, it only pushes you towards one direction. Away from the concept. Listen up, Hallmark: we are trapped beasts. Our close friends are married. With kids. We rarely see these beloved souls. Or they’re in very serious relationships and we know we’re about to lose them. We feel this barrage and resent the pressure, thus embrace the alternative: a fantasy Bruce Wayne, James Bond lifestyle. Yet after doing the math, Hallmark actually has it right. Instead of one Valentine’s card, we end up buying two or three. It will take roughly three months for us to realize these lifestyles are unattainable.

Before Christmas, Tinder land was very quiet. It was holiday party time, then family time, and suddenly it exploded the day after Christmas. New York City was back and looking for love! Most women already have their plans lined up, but best to get a good start on love in 2014. I personally have four dates calendared in.

I did get a date in right away. Hot single mom from OKCupid popped back up on my radar thanks to a Facebook post that led me to her blog, which hinted she was not seeing someone. To update, about a month and a half ago we exchanged lengthy messages every day for roughly a week about our lives and histories. She went on a long trip and returned. During that trip, I met a nurse from Tinder who I really like. The nurse was coming off a relationship, we went out three times, and it has been in a holding pattern the past three weeks. She is not ready to date and has other issues right now. The kind of issues that led her to move back home I presume (before I met her). The day I set up a date with hot mom, the nurse informed me that she’s just not sure about anything and basically killed any hopes I had. However, we netted out that she’d like to still hang out. Something I’m not sure will actually happen. Anyway, I needed to go out with hot mom now and I was excited: the timing of both our prospective long-term relationships started and definitively ended simultaneously!

My attraction to hot single mom is strong. She is an amateur erotic novel writer. I’ve read two of them and they’re solid. Her words simply draw me to her, not to mention it’s full of hot sex. We met for drinks, then I asked her to join me for a bite. I wasn’t sure about how this date was going. She spoke about the date she had the next night, the relationship she just had (with a dominant and the dominant’s friend, another dominant), her NYE sex party, and how she doesn’t want a traditional relationship at the moment. As we went further into the night, she spoke of poly amorous relationships and asked me if I was interested in the concept. Now scroll back up this post. Did I say James Bond? I meant Austin Powers. Yeah, baby! Still I wasn’t sure if all this talk was the type that you hear from a sex therapist (she could be one I believe) who’s trying to help a prude (me, when compared to her). I verbally committed to read a book with her, which was recommended by a dominant she is going to date. The Ethical Slut. At the end of the date, we made out on the street before I put her in a cab.

Reviewing all this in my head, I’m able to identify something I want from a woman. The power to thrill me intellectually, which translates to physical desire. Even more ironic is that this is the first post on my blog about settling down, committing, and the journey to fatherhood… yet I’m writing about starting a two-person book club on open relationships. Stick around. This is just the beginning.

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