Five Down, Many To Go

Terrified that having a puppy (as lovely as she is) would ruin my social life as I know it — I’ve been quite the busy dater this past month. I can’t blame Lucy entirely for my new-found interest in getting back into the scene — it’s also the chilly weather that reminds me of cuddling under covers with no clothes except socks, the smell of pumpkin spice that remind me of home, and just how handsome men look with rosy cheeks and scruff that’s a little too out grown.

And also, the fact that I’ve been single for over a year now…

Given, I spent some time (okay, maybe a lot of time) hung up over Mr. Possibility. And even, yes, sleeping with him far longer than I should have. But now that my past is both figuratively and literally miles and months behind me, I have the urge to meet someone. Doesn’t have to be my forever-and-ever guy, but just a guy….would be nice. It’d be comforting and exciting — and hopefully, it’d spread some of my natural optimism into my romantic relationships, instead of the negativity that consumes them recently.

So, with a few clicks of my mouse on three online dating profiles (yes, three!), enticing friends to set me up with the eligible bachelors in their lives and throwing some flirting glances across practically each room I graced, I somehow managed to have five first dates in the past four weeks. For me — who walks a dog three times a day, works 40+ hours and runs three miles at least five days a week — dating can sometimes be difficult to budget into my time. But, with as much hope I could muster without making my eyes blush, I jumped head (not heart) first into the scary Manhattan pool of singleness.

The first date, the guy upped his height by six inches, which isn’t really fudging on your online dating profile, it’s just flat-out lying. And while I know how tall a dude is shouldn’t affect my taste too much — it really does. Maybe it’s my own personal hangup or my need to feel small and protected around someone I’m dating, but it’s not something I’ve been able to compromise. I prefer 5’10” and above, but if I met the man I’d been waiting for and he was 5’9″ — I betcha I could get over it. This particular guy arrived before me and was already sitting down, so I didn’t know his 6’0″ claim wasn’t true until after the drinks had been drank and the bites had been nibbled, and we stood up to leave that I realized his very white lie. I wasn’t wearing heels and at 5’4″, he wasn’t even a head above me. The conversation hadn’t been intriguing enough to entice me for another date and his shortness in character and in height made it easy to respond with, “Let’s be friends!” when he texted the next day. Of course, no response.

The second guy was interesting enough — but mainly because he reminded me of my gay husband, J. He was flamboyant, incredibly social and made some joke about how he psyched his parents out at Christmas one year by saying he may bring a guy home (Red, red flag!). He talked more than I did, insisted on walking me home and didn’t attempt to kiss me goodnight (which I didn’t expect, either) — and still texted the next day. I did the same routine as I did with the first guy and this one quickly stopped contact, too.

The third date was the best of them all — over sushi and some wine, I chatted it up with a friend of a friend. The rapport was fast and clever, the shared glances were subtle and enticing, and I understood why my friend thought we’d get along. However, as I’m prone to picking up on what could be deal-breakers way sooner than I have in past courtships, I noticed that the majority of the conversation wasn’t targeted at me, but about him. He was the classic one-upper (which would be his Mr. title if he actually made it into this blog for more than a paragraph), and by the time the check came and left, I was ready to not compete in the conversation anymore.

The fourth date was my first Match.com date, and I was excited to see how powerful their magical matching brew really is. I showed up earlier and caught up on reading, while waiting for him to arrive. I could tell from the first smile that he was shyer than most men I date. He was looking forward to going to Comic Con, came from a good family and lived on the Upper East Side. (Which frankly when you’re on the West Side, is nearly too much distance to handle.) I was attracted to him and his politeness was overwhelming, but I didn’t feel that thing. I know sparks don’t always fly in the very beginning and they sometimes take time to flicker, but I think you know if the flame can be ignited, even just a little bit, from the start. He walked me to the bus stop and kindly hugged me goodbye. We haven’t spoken since, and I haven’t noticed.

The fifth date was on Saturday, and is still a little too depressing for me to share in vivid detail. What I will say is that I now know that some preferences are set in stone. Like, I don’t care for someone who checks the score of the game — and talks about it — more than once at a dinner table. On the first date. Or someone who gambles or plays pokers… a lot. Or who doesn’t have respect for animals. Or is sexist about the toilet seat. But mostly, if they think voting for Mitt Romney is a vote for women. Nope, not interested. But proud of myself for walking out of a date for the very first time. I have a feeling it surely won’t be the last.

Needless to say, I haven’t really found someone I’m interested in, even after making a whole new commitment to putting myself out there. I always try to find the lesson in everything — the silver lining that will make it all make sense, that will make it all seem part of a grand scheme, or some predetermined fate that I can’t even begin to visualize yet. But really the only thing I’ve become convinced of the past month is…

…dating can suck. It can honestly, really, really suck.

It’s constant disappointment. It’s something being off even if you’re not quite sure what that something is. It’s trying to avoid the wolf underneath the sheep, and to find the sheep that’s hidden by your mesmerization with the wolf. It’s hoping for a someone you’re not entitled to meet just because you’re you. It’s a lot of scheduling and work, compromising and wondering when it’s all going to fall into place. Frankly, it’s so exhausting, I’m tired of writing about it — but…

…I still want to do it.

Even if five not-so-great dates turn into hundreds of bad dates. Even if I have to endure Republicans and receding hairlines, guys who are in denial about their height, ones who aren’t out of the closet yet. Even if I have to meet all of the very, very wrong guys that aren’t a great fit for me — I’d rather do it. I’d rather suffer through and keep going. Keep dating.

Because you can’t find the right one if you don’t know how to spot a bad one. And you can’t get what you want if you refuse to go after it. Or to let it go after you. You can’t have your heart feel those many wondrous things it longs to feel if you don’t open it wide enough to let someone touch it.  To capture it.

And even though it would be so lovely, you can’t skip the sucky first dates if you ever intend to find a guy who you can’t wait to go on a second date with. Or a third. Or five. Or many, many more…

Little Miss Too Much

So this is the point in the blog when I admit that once upon a time, I competed in pageants.

Now, before you go imagining Toddlers & Tiaras, I was far from your average beauty queen. I won a handful of titles but mostly enjoyed having permission to dress up for no particular reason at all. The older I became and the more of a feminist I grew into, I realized how parading oiled up half-naked across a stage and being quizzed on my current events knowledge with a pound of makeup on my faces can seem a little contradictory and not give me the best image of integrity. And while I did attend school with the infamous Ms. South Carolina (I met her, she’s actually quite smart), pageants taught me how to be comfortable on stage, how to own my power when I’m nervous, and how to fake a smile even when I’m shaking.

Most Photogenic Winning Photo 2006/NC Pageant

When I first expressed interest in this tired Southern tradition, my mother -who is far from the Débutante; she’s everything but – couldn’t understand why I would purposefully encourage someone to judge me. I was raised to believe everyone has their own level of loveliness and by words of the renowned Ms. Eleanor that no one can make you feel inferior without your consent. Fearing I’d compare myself to the other contestants and lose some of my self-worth and value, or worse – develop an eating disorder of sorts, she wasn’t easy to convince. She eventually gave in, seeing the potential confidence and public speaking ability it could give me. However, I had to vow to be honest and to remember beauty is as beauty does, and while it may only be skin deep, I’d have to keep my head high and not fall too hard into the pageantry world.

And while I was part of this microcosm, more than the elegant dresses, the spray tans, and the dazzling crowns that still have their place in my childhood bedroom, being a so-called title holder taught me how to think on my feet. Or really, in 4 inch sparkly shoes. It has been a while since I traded in my mermaid dresses for a voice recorder, and my economy-sized hairspray for a higher, modern hemline – but throughout my journalist career and adult life, being able to think quick and speak elegantly is well worth any dues I paid as a pageant girl.

However, as a 20-something fielding cascading lines of bachelors who strut the streets and trains of Manhattan – while I often play the part of judge, picking the contestant who is a winner in my book, sometimes, I feel like I’m back up on that stage, lights shining, and gracefully fighting for a title. In the past, that title was always Ms. Girlfriend or when my overly premature and idealistic self would take over, Ms. Love of His Life or better yet, Mrs. Right.

But the one title I always felt like I claimed without trying (or was it trying too hard?) was Little Miss Too Much. All those lessons about thinking on the spot flew out the door and putty I become in the hands of the man of the hour.

Whenever I started to like a guy or date him regularly, I always developed this fear of being “too much.” We’re instructed by the women older than us, by our friends who have been there, by everything female that surrounds us that guys are easily intimidated and deathly afraid of commitment. I won’t deny either of those statements, even if they are rather generalized. However – in an effort to prevent the stepping-on-the-loafers of men who I hoped would eventually deem me worthy to be their girlfriend and tie up their loose ends with other ladies – I held myself back. I acted uninterested when I was highly intrigued, I bit my tongue instead of speaking my mind, I held back my frustrations and my longings instead of expressing what I felt, when I felt it. Because while men want to sleep with the beauty queens and date the women who hold the highest title, I had never met a man who wanted to date Little Miss Too Much.

That is, until I did.

When I decided to date above the curve, to raise my standards, and demand more out of a partner, I stopped worrying about being too much to handle. And in return, I found guys who wanted someone just like me – who may be outspoken and demanding and opinionated – but they find it beautiful and inspiring. Because really, those apprehensions come from insecurities and also partly derive from the remains of men who exited without a notice or didn’t care to stick around when the going got going – or got tough. From the dudes who prefer women to be their escorts about town and hang quietly and nicely on their arms, without pressuring or condoning or challenging them. They are the ones who would never fit the bill of what it means to date a woman who has things going for her, who wants to be with someone who not only encourages her thoughts, but engages in wild conversation with her.  They are the guys who are too little for a girl who is seemingly “too much.”

And those emotional outbursts or those topics that make our blood boil don’t grant us the title of the crazy ex-girlfriend or the gal who pressured a man into a relationship, with no avail. There really isn’t such a thing as being too much unless there is also such a thing as being too human. Because if we didn’t worry from time to time, if we didn’t let certain things crawl under our skin because we were passionate about them, if we didn’t desire to only be with someone who only wanted to be with us – then what would be the point of attempting anything? Or developing opinions, tastes, and desires? Or deciding how you’ll give world peace to the nations, as every pageant coach instructs you to stay abreast of?

Now, when I’m dating and when I’m with Mr. Possibility and I feel the need to test the waters that I normally wouldn’t have waded for fear of sending a potential partner sailing away- I instead make quite the splash. I don’t make excuses for why I’m upset or why something they say rubs me the wrong way or if I don’t agree with a viewpoint they stand firmly about. I don’t pretend to be someone I’m not just to be crowned Ms. Irresistible. I’ve learned they’re competing to be center stage in my life as much as I am in theirs.

Because while pageants may have given me great balance and the ability to bullshit when need-be, they also showed me to be my greatest and most forgiving fan. If you trip, you trip – and you keep walking. If you stutter, you stutter -and you pause and move on. If you lose, you lose – and you try again.

And if you feel like you’re being too much, you put even more out there and give a little extra kick to that hip. Because no one – not even a pearl-ridden Southern girl with hair almost as high as the heavens – makes excuses for being herself.

The Anonymous Dater

The ironic truth about living in a densely populated city is though you are surrounded by people, it is easier to go unnoticed than residing in a small Southern town just West of the Tennessee line. You see, unlike those tiny towns I grew up in, in New York, people realize they could know your business if they asked, but most of the time,they  just don’t care.

Though we may never realize it – any place we decide to go and grow roots – there will always be more strangers than friends. There will always be people coming and people leaving, and even if we travel the same route or road the same way, every single day, there will always be someone new who shows their face. And the reality of it is, if we’d like to not display ours for the world – we don’t have to. Especially here.

If you want to be anonymous, the second you take a step out of your apartment, you can put iPod buds in your ear, raise the volume on a song with a beat to wake you up, and off you go. To the subway, of course, if you’re trying to lay low – after all, if you ask the monetarily blessed of Manhattan, they feel sorry for the “poor people” who have to take the train. Down the stairs you’ll ascend into the darkened transit and there you will sit alone, with a very rare chance you’ll recognize anyone at your stop. After bravely leaning against a pillar or walking the track to pass the time, your chariot will eventually arrive, but there will be no Prince to lend his hand as you step up. (You don’t need his help anyways). As you ride uptown or downtown (the direction never quite matters), you’ll sit to yourself, music still playing (but probably lowered), as you read the latest magazine or yet another Vampire-inspired novel that I still can’t jump on the bandwagon for. When the doors open to your destination, you’ll exit, without slipping a word to anyone or touching anything. Out onto the street you’ll rush, walking past people eying an underground performer, a foreign family unsure of which colored-line to take, and a man who thought your blue scarf looked stunning on you. But did you notice? No, you were lost away in whatever playlist you picked, thinking about getting to instead of living in. And then, just as one could predict, your feet touched the glimmering pavement and you blended into the crowds, bumping your way through elbows, and mumbling “excuse me” only when absolutely necessary.

It is one thing to be an anonymous New Yorker – the city is actually quite ripe with them. They are those people who’d rather not be bothered by the things you can’t predict or the chance conversations that can actually be the very thoughts hat turn your perspective. They are the ones who simply don’t want to be interrupted as they go from point A to point B, they just want to leave and arrive, without experiencing anything between.

But what they don’t realize is so much of the best of life is in the in between. And like one of my friends always says, “If I’m going to pay this much to live here, I’m going to get my money’s worth!” She’s right – if you’re ignoring the characters and the connections that  your address entertains, what’s the point?

After all, if you’re anonymous on the streets, do you really expect to meet anyone captivating? As much as we all complain about our single status and how we are never noticed by the type of guys we like, are we making ourselves available for someone to approach us? As lovely as it sounds that a man was so astonished with our beauty, that from across a crowded subway cart, he battled the straphangers to simply ask our name, and then vowed he’d find us again (maybe through Craigslist’s Missed Connections) – don’t you think that’s a little far-fetched?

Worse than being an anonymous resident is being an anonymous dater – but more often than not, they are one in the same. I’m lucky to not be a shy type of person, but even with as outgoing and normally fearless as I am in the dating market, I have to push myself. I don’t always feel my very best or my most attractive, but I also know that confidence is more important than anything – zits and bloated tummies aside. Anyone, man or female, is intrigued by someone who is intrigued by themselves. And if your eyes are peering toward the pages of a book for ten stops or at your drink for thirty minutes, how will anyone see that fire that only belongs to you?

They won’t.

There are times that call for anonymousness. Sometimes it is refreshing to ignore the rest of the world and go at your own pace, without worrying about what someone else prefers. It is a nice cloak that New York offers to its inhabitants – as if it is saying, “I know I’m tough on you, so every once in a while, I’ll let you disappear.” But remember, that robe is only meant to be momentary -not permanent.

Because the longer you engage the anonymous title and make yourself more into a stranger than a person, the more difficult it is for someone to remember youR name. Or even worse, the more you lose touch with who you are, drowning in a sea of people you’ve never seen and have stopped noticing. Take the chance – take the dive – and try looking up, instead of looking away. Remember to love yourself and know that that love will translate into conversation and give you that energy you need to be alluring. Notice the unnoticeables, listen to the city instead of the Biebs, read the lines on someone’s face instead of the WSJ, and give yourself more credit than just a statistic in this city’s census. Make yourself someone who lives in your own life, in this city, or wherever you are- not just someone who is passing by, anonymously.

Don’t Push the Button

Manhattan is a mere 2.3  miles wide by 13.4 miles long, and yet it is one of the most densely populated cities in the world. To provide housing, nourishment, and entertainment to the millions of dreamers who float on this small island, the only way to build…is up.

And up is where New Yorkers go. To the tallest skyscraper, to the top of our careers, to the highest of heels, to the most impressive of social circles, to the most diverse collection of interests, intelligence, and conversation. To the corner office on the highest floor, to the penthouse suite of a high-rise, to the man who towers at 6’4″ with one of those impressively heavy credit cards that are by invitation only. To get to where we’re going, us, the united and tired people who refuse to live in any borough but Manhattan, we do it quickly. We hustle to catch the train before the conductor warns us of the closing doors, we hastily parade through tourists admiring the sites we probably take for granted, and we are always keeping our eyes peeled for the next opportunity, for the next businessman to treat us to dinner, for the next big thing that’ll take us closer and closer to the peak we all seek.

Because we’re in such a hurry to get to our next destination, no matter if it’s work, our dwelling, or the surprisingly difficult to get to top floor of Macy’s – we take the elevator. Just like the cobblestone streets in the Village and Ms. Lady Liberty herself, some of the shoots in this city are scarily old. But, like Mr. Trump’s towers and the luxury buildings on nearly every tenth corner, some elevators are so fast, so motionless that they’ll take your breath away.

Regardless of their age, though, there is something strikingly similar about each of these mechanisms: the “close door” button is much more worn and used than the “open door” one. It makes sense – if we’re always chasing the next fire to start or to put out – don’t we want to get in and get going as soon as possible?

I don’t usually take the elevator, mainly because my building is a walk-up and my office is on the fourth floor – but when I do, the elevator etiquette is almost always the same. The men step aside to let me, the lady, in first and then they follow behind in suit, as if they’re protecting me by ensuring no one gets in who shouldn’t. We each push our buttons and face towards the exit, without striking up conversation, by smiling politely to avoid awkwardness. And then, as we’re all settling into the spot we’ll refuse to leave for our entire ride up (or down) – someone inevitably pushes the “close door” button. Not once, not twice, or even three times – but as many times as it takes until the door closes and we cascade up the shoot.

I’m convinced most of the “please, please, please close” buttons don’t work or they’ve lost their power over the years – but as much as it irritates me to watch that person insist on moving faster than the elevator already does, I have to admit that for a long time, my approach to love and life was even more diligent than his/her finger.

From the time I decided I wanted to be a writer who lived in New York, I fought tooth-and-nail to make it a reality. I took on more responsibility than I should have, I had more internships than I needed to, I took on titles and roles that weren’t necessary, and I saved more money than I ever anticipated. I walked away from relationships I thought would hold me back, I graduated a semester early from college, and I worried endlessly that my dream, what I thought was my destiny, would never get here.

I closed many doors and never looked back because my eyes were set to what I thought was the end-all-be-all, the top flight of my life. I was so focused on the doors to spread apart and to step out into the world I knew I was supposed to be a part of, that I couldn’t have gotten here faster.

And while I do not regret my path and any of the things I left behind to become a New Yorker or a writer – I sometimes wonder if I needed to rush. Because once you get to where you’re going – you’re there. Could I have missed doors that opened because I wanted the elevator to close so badly? Could I have missed a floor that could have brought me happiness because my sights were set to narrowly to my goal?

Haven’t I done this in love, too?

Once I realized a relationship wasn’t working or the guy let me know he no longer wanted me part of his life -I made a run for it. I jumped on the fastest-ride to mourning, getting angry, and eventually attempting to forget about the certain he-who-should-not-be-named. I figured, no matter if I sprinted towards the doors of the old relationship to try and catch them before they slammed shut  – they would eventually close. Even if I push the “going up” or the “come back to me” button one hundred times, it would be one hundred times wasted. I turned my back often times on letting someone catch the elevator with me because I just wanted to go, to run away from any possibility for fear I’d get hurt. Yet, I always had one eye carefully watching for a door to open, for it to be the moment, when I met the man who would change it all. To stop on his floor, instead of figuring out which one I belonged on.

Like the New Yorker I always was, but now can officially claim, I never give myself a moment to breathe. As much as I don’t have patience with men, with my career, with the train when I’m about to be late to work – I have even less patience with myself. Nothing is ever good enough, clever enough, smart enough, pretty enough, shapely enough, or high enough. I want more and more, faster and faster, tougher and tougher, fancier and fancier -and I don‘t want to wait. I may not push the button to make the doors close, yet I push my own buttons constantly.

But, I’ve finally realized that the span between the lobby and the penthouse is never really that long.

Sometimes the cart is empty and you go from bottom to top without hesitation. Sometimes people come and go with each floor that passes, and sometimes a child wants to make the whole screen light up. Sometimes the doors must be held open to let something large fit, and sometimes you go up an extra floor just because you’d like to continue locking eyes with a handsome stranger (and to figure out which one he’s on). Sometimes there are technical difficulties, sometimes the air conditioning goes out, and sometimes it goes down before it goes back up.

And sometimes, when we’re luckier than we know, the doors open to a place we never anticipated. This is when instead of rushing – we step carefully out into the unfamiliar space and hear our click-click against the floor. And there, we decide perhaps we can enjoy the ride to the top and experience everything along the way. No need to push the open or the close door, and especially not our own. If we so choose, we may decide to go back down or pick a different level, and not worry about the pressures we place on ourselves or about time it takes to go floor-to-floor.

Because when the time is right, when we’ve had patience with ourselves and with the masters of fate, we know the elevator will always go up. And if it doesn’t, we’ll be strong enough to take the stairs.

P.S. Confessions of a Love Addict is celebrating Valentine’s Day a little differently this year. We’ll make it more about the single ladies and less about flowers that’ll die in a day. Submit your Valentine here.

It Just Wasn’t There: Mr. Millionaire

When I moved to New York on a rainy March afternoon, my flight was delayed by two hours, I got a run in my panty hose, and I arrived with nothing to my name, except bags and a friend’s couch on loan. Even once I moved uptown to my humbly priced and furnished apartment and accepted my job – my life in the city of dreamers was far from dreamy.

I’ve never, even in my worse of days, regretted moving to Manhattan, but for the first three or four months, I was lonely, broke, and living off visions of what I hoped my New York life would be like one day. And so, when I spent an entire week without having a drink, meeting anyone new, or chatting with a girlfriend – I gave in and joined an online dating site. OkCupid, to be exact.

I’m still not sure what I think about digital dating and it is something I’ll explore at a later date in this blog, but at the time, I honestly used it as a way to meet people. If the only thing I had to do on the weekends was to go out with BlueEyes28, then at least I was doing something other than renting Blockbuster Express movies. I wasn’t very open on my profile, I didn’t post many photos, and because I wasn’t technically “looking for love” (was a tad creeped out by the idea of cyber romance, to be frank) – I didn’t want the dudes to know that.

Come to find out, sometimes there are worse things than having no friends: awful dates with strange men. One dude who claimed he was 29, turned out to be 36, another asked me when I was ready to have children within the first twenty minutes, a very odd one cried when he talked about his late cat, and another who said he was six-feet-tall, was barely my height. So when Mr. Millionaire shot an arrow towards me on OkCupid, I didn’t have the highest of hopes.

So instead of meeting him right away, I decided to invite him to Gchat. I figured if I could determine how he responded to my interrogations, maybe he would be an enjoyable date, as opposed to a flat-out terrifying one. Surprisingly, he was very easy to talk to. And though they were just typed sentences, we seemed to click.  I wasn’t sure how much we had in common, but when he asked if I’d go to an incredibly well-rated restaurant with him, I happily agreed. I mean, I was still living off Ramen – so how could I decline an invitation like that?

I usually attempt to be fashionably late to dates, just to keep them waiting, but somehow I arrived earlier than him, gave the name, and sat down to for some much-needed water. In the ten minutes it took him to join me at the table, I admired the scene, the smells, and the glamarous people who put my H&M dress and Carlos Santana shoes to shame. The entry-level editorial assistant in me wondered, “What am I doing here? The menu doesn’t even have prices on it!”

Before I could get too down on myself, Mr. Millionaire, in his 6’5″ stature walked in the door and I gave him my best “Oh, you look different than your pictures” fake smile. He started rambling about the traffic and how he just told his driver that he’d walk a block since it was taking so long, and he hoped my commute wasn’t bad. I started to tell him the subway and walking was just fine, but refrained and settled on a nod. When the waitress arrived, he went ahead and ordered us appetizers and cocktails, without my opinion, and then turned to start quizzing me. As I went into first-date protection mode, I studied his face, his movements, and clothes and decided this German man, was in fact, wealthy. I don’t know how scientific or accurate this is, but sometimes, you can just look at someone and know they have money.

He wasn’t an unattractive man and he had a very confident air about him. Once he seemed pleased with my responses, I became brave enough to ask him what he did for a living, and the rest of the standardized getting-to-know you questions. Had he not ordered us what I was sure was a bottle of wine well over $100, I probably would have spewed it across the room when he oh-so-casually stated:

“Oh, I own my own investment company. We have offices downtown in the Wall Street area. Currently, I’m living alone two buildings down from the Empire State in a two-bedroom on the 34th floor. It wasn’t my first pick, but it’s nice. I also am the head of a charity organization that’s really important to me.”

At this point, I considered telling him that I live on the border of Harlem, in a very, very small studio that isn’t air conditioned, and I was currently mostly friendless. But before I could say anything, he looked at me and matter-of-factly said, “You have very beautiful eyes and I’m enjoying your company – you seem like you have a lot of ambition and passion. Would you want to get drinks after this?”

Even though I wasn’t sure if I was fully attracted to him, what I thought about our vastly different lifestyles, and his nearly-bald head – I did what any intrigued young woman would do. I replied, “Well, of course!

He didn’t attempt to kiss me at the end of our date, but did ask me if I’d like to come over two days later, to see his view, and maybe watch a movie. Knowing full and well what that usually turns into, I considered passing on his offer, but he was leaning into the cab, as I had always dreamed, and I did want to see what a real-life New York apartment looked like, so…I simply replied “Ok” and kissed his cheek, before the cabbie drove away.

I decided that if I’m going to be lonely in a city of millions – I should at least entertain the company of Mr. Millionaire. What harm could it really do?

If dating and relationships are meant to teach you not only about your wants and needs, but about yourself, then Mr. Millionaire showed me how very little I actually need, compared to what I thought I wanted. His apartment is unmistakably beautiful: he shipped all his furniture from Germany, commissioned artwork that featured portraits of the city, and he (or rather, his maid) kept the place immaculate. As for the view, I can’t give it justice in words as well as this photo can:

But even though he had this incredible residence and kissed me outside on his balcony for our “first kiss” as the sun set against the Manhattan skyline – something was off. As much as I tried, I just didn’t feel that indescribable connection that we all lust after and can never really find, unless we actually stop looking for it.  He wasn’t a bad guy by any means – his success, ambition, and humbleness impressed me, and he always did what he said he was going to do. It was just…it didn’t work. Maybe because there was a 10-year age difference or we literally lived in completely different worlds in the same city – but there were things about him that drove me crazy.

When we ordered takeout, he insisted on putting everything on plates and setting the table just so. When I gushed over the fact he had an actual washer and dryer in his own apartment, he admitted he sent his laundry out to be done for him. When we did watch that movie and I went to his fully-equipped kitchen to get some water – I realized he didn’t have any food, to which he casually said he only orders takeout, goes out, and hates to cook. He read my articles, critisized them, and though he said I had talent, he was more interested in the sex pieces I freelanced on the side. He didn’t seem to understand what publishing was about, nor did he really care too much. And when the World Cup rolled around, he said in passing he’d be staying in South Africa until it was over. Oh, because anyone can just pick up and do that.

Perhaps the most telling sign that I needed to stop seeing Mr. Millionaire, regardless of the many wonderous restaurants and events he took me to (and was planning to take me to) – was when he started to go past first base and my reaction was to run to the bathroom to keep myself from crying because it felt…so wrong. I used every excuse to let him know I needed to leave and instead of flirting with him from inside the cab, I sobbed in it the whole way home. Not due to him or his actions, but because I knew I was keeping him around for the wrong reasons.

While I never thought New York would be like Sex & the City (introduce me to one writer who writes one column a week and lives in the West Village and I may change my mind) – I did have this romantic idea about what my life would be like. And with Mr. Millionaire, I got to experience that. I was fancy and could order anything I wanted without looking at the menu, and I was lucky enough to go about town with an extremely gregarious gentleman.

But what I realized was designer clothes, apartments, views, and men can bring you a lot of joy – but they will never be enough for love. I really did want to fall head over $800-heels with Mr. Millionaire, yet not because of who he was, but for the idea of the life I could live with him. A life that didn’t include me worrying about money, traveling, or living arrangements. Sure, it would have been easy – but would it have been worth it?

As for me and my city, I’d rather make my own fortune than marry into it, eat Chinese food out of the container, naked in bed instead of sitting properly at an imported table, and be with someone, who regardless of how much money they make or what the view is like out their window – I can’t deny the magic between us. Nor would I ever think to pull away when he goes for a home-run.

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Until We Meet Again

Yesterday morning, as I rolled (or dragged) my red suitcase up and down several flights of stairs on my way to the airport – I took a mini-trip back in time.

Almost a year ago now, I lugged this same suitcase (along with two additional ones) from North Carolina all the way to a friend’s couch in Brooklyn. I distinctively remember stepping out of the cab on my friend’s block and the March air hitting my face as if it was saying: “What the hell are you doing? Don’t you know you don’t have a job? Or a place to live for very long? Are you out of your mind?”

Maybe I was crazy (perhaps I still am) – but somehow, I found myself moving those same three suitcases into an apartment uptown and starting my first day at my job, three weeks later, on April 5. When I think of my journey to New York, I’m often dumbfounded by how, for whatever reason, by whatever twist of good fortune and faith, all that I wanted…happened.

The decision to move to the city wasn’t ever really a choice in the first place. I made my mind up a long time ago that I would live in New York (not a borough, but Manhattan), I would be a writer (magazine first, then an author), I would run in Central Park (except in the winter), and I would find the love of my life.

And I believe I have. If anything challenges me, brings me unsurpassed joy, makes me feel adored and lucky – it is the boisterous and beautiful island of Manhattan.

Leaving yesterday, I felt a sense of dread. Of guilt. Of sadness. Because here I was, leaving my love at such a special time of year. I could hear the city saying, “But Lindsay, don’t you still love me? Don’t you want to spend your Christmas here? Look at how much we’ve been through together, why are you going back to the South?”

Don’t get me wrong, I was excited to see my mother’s and father’s face light up when they see me walking towards them or celebrating the holidays with childhood friends. I could almost taste the sweet tea, the biscuits with honey, and the fried-is-fine-by-me seasoning. I was looking forward to having a puppy to keep me company at night, sleeping in until 10 in the morning, and of course – Christmas morning with those I enjoy the very most.

But as that airplane took off, as I watched the glittering skyline disappear behind the tailwind – it was as if I was abandoning a piece of my heart. While I didn’t tear up, I did sigh and dive into my New Yorker magazine which outlined 20 reasons why I should love New York. I did thoroughly enjoy the issue (as I do every year), and it inspired me to make a list of my own.

So, my dearest love, since I’m leaving you on your own for ten days, don’t forget just a handful of reasons why I adore thee:

1-     At any given moment, you can step outside of your office, onto the train, or just walk down the street and hear a few different languages.

2-     It harbors and caters to the artists, to the dreamers, to the crazies, and those who dare to light up the lives of others. The passionate and determined are the successful.

3-     While the single women may outnumber the single men, it is nearly impossible to not be bought a drink on a Friday night. Hmm – or really any night.

4-     I can go anywhere in the five boroughs for $2.25 (soon to be $2.50, sigh).

5-     Even though it has a bad rep, there is always someone there to open a door, help you carry something heavy, or hold the train or elevator door open for you.

6-     The moments on the train when you see another train on a different rail and catch the eye of a stranger – fully knowing you will probably never see them again, but in that second, you shared a moment that somehow, in a strange way, meant something.

7-     An entire afternoon can be spent in Central Park and there is never enough time to give any museum a justified tour.

8-     If you’re feeling down, upset, discouraged, or just frankly pissed off – walking through an un-crowded portion of the streets will energize you.

9-     Those moments where the city seems silent. And those where it is filled with so much enthusiasm you have to smile.

10- Heels are not only accepted, but highly encouraged and those fashions that were frowned upon in the south, are gladly gawked at here.

11- Heartbreak be damned – there are more than enough pastry, ice cream, cookie, and Gelato bakeries or cafes. Not to mention endless amounts of fantastic wine and interesting people to meet who will force you to forget about Mr. Yesterday.

12- Staring in the city is not only allowed, but supported. And the views, where they be characters or skylines, are beautiful and entertaining.

13- If you have a day where you stop believing in love, all you have to do is look around. There is kindness, compassion, and romance on every corner.

14- You can decide to be in your own little world with headphones and high heels or simply take them off and be welcomed back into the Manhattan universe.

15- The city forgives you if you curse it one minute and apologize the next. Doesn’t even ask why – it just gets it.

16- If ever in doubt, throw up a hand, get a cab, and go home.

17- Possibilities lurk even on buses coming to and from the airport.

18- There are a million and one resources to help you find not only friends, but people who have similar interests and passions that you do.

19- You can play tourist whenever you want and then decide they are the enemy the next morning.

20- After a while, or maybe just a short span, the lights, the wonder, the people, the food, the sights, the experiences – still feel just as magical, but even more so, they start to feel like home.

And that’s what it is. The love I always wished for, the address I used to doodle in my notebooks, the bylines I use to imagine – are not the dreams of a young girl anymore, but the reality of, the home for – a woman. Even better, a single woman, who has the freedom, the opportunity, the brilliance, and the bravery to tackle this location, this decade of being a 20-something – on her own.

Well, maybe not completely alone. This city will always be on my side, calling me ridiculous, yet sweetly reminding me: “You’ve got this, lady.

And just so you know, New York, I’ve got you, too. And I’ll be back – I may bring you a little sweet from the south to up your charm a notch. Until we meet again…