“My milkshake brings all the boys to the yard and they’re like, its better than yours, damn right its better than yours – I can teach you but I have to charge” – Milkshake, Kelis

Clearly the milkshake isn't working.  *Puts bartending skills to use and blends alcoholic beverage to lure the boys to the yard*
Clearly the milkshake isn’t working. 

Kelis sounded like she was onto something, so I thought it would work for me, but I was wrong.  My milkshake didn’t bring all the boys to the yard :(.

My social life has been rather active (if I do say so myself, if I do say so myself, if I do say so myself –> I’m actually making a mockery of Jay-Z’s verse in Beyonce’s Drunk in Love – I digress).  I’ve been indulging in the nightlife scene as much as possible; happy hours, lounges, game nights, etc.  You name it, and I’m in the mix.  However, it seems that the organic method of meeting that special someone hasn’t quite worked for this unicorn.

It’d been roughly nine months since my ex and I parted ways so I thought I would take the advice of my sister and give online dating  a serious try.  I’d tried it before, but barely logged in to make the most of the services that were offered.  I opted for match.com this time around because some very close relatives of mine have found success (thriving relationships and even marriage) on the site.  I made the decision to join in September of 2013.

Why September? Well, I thought it was fitting – new job, new experiences, possible new love……  I made September my “yes month” (after being inspired by watching Jim Carey’s Yes Man); I agreed to say “yes” to pretty much any opportunity thrown my way (provided it didn’t endanger my safety or health).

Creating a Profile

There I was, Match.com and I.  I signed up for the three month membership and proceeded to personalize my profile.  The process was a bit intimidating.  Creating a luring “headline” to catch the attention of a suitor (I found that something short and comedic worked wonders) and to write about yourself (which can be weird as you want to ensure that you write just enough to share your world, but not too much; lest you be deemed a narcissist).  The main point is to find a happy medium and to work on the next thing, posting photos.

To selfie or not to selfie, that was the question.  I didn’t know what to do and asked myself many questions before doing so.  “Do I post a selfie? Do I post pictures of myself in a full face of makeup or in my natural state?  Do I post pictures of myself in scandalous outfits or do I post pictures of myself clad in professional attire?  Which pictures will generate the most traffic to my profile?  What works on this site?”  I was over-thinking it and I knew it, so I told myself to “chill the f*@k out” and relaxed.  I went the minimalist route and posted pics that I was most comfortable with; I posted five to six tasteful shots that showcased my my smile, physique, style, and my sense of adventure (I included a candid shot or two of myself involved in some sort of action).

After I tweaked my profile;  posted pictures, described my interests/hobbies, shared my spiritual beliefs (and what I would want my potential mate to have), and selected the physical attributes that I wanted in my “match” (age, height, stature, and race), I was pretty much set.  I was content with my profile and simply sat back and waited for the MEN (sorry Kelis, I don’t do “boys”) to come to the yard.

The Waiting Game

This might be THE most intimidating part of the match.com experience.   Although the site sends you daily matches, you don’t have to sit around and wait for that.  You have the option to view the profiles of the sex (man or woman) that you are interested in.   This was fun, checking out pics, reading profiles, learning about weird idiosyncrasies, you name it, it was all at your disposal.  Hell, you even had the option to add the match.com app to your phone so you could have access everywhere (not just on your laptop/desktop).  Sounds great right?  However, there was a catch.  While you have the option to peruse as much as you like, I learned that the profiles that you view were documented.  This meant that the men that I checked out knew that I viewed their profiles.   What made it even more awkward was when they would check my page out, but not reach out (or in match.com world, send you a virtual “wink” or send you a message to show their interest).  Yeah, yeah, yeah, I did it to them, but I felt some kind of way when it was done to me.  I felt like a slave on an auction block being scrutinized for flaws rather than perfections; I can’t front it was unnerving.

Despite the aforementioned unsettling scrutiny, I continued to approach men virtually.  Why not, I have no problem doing it person, so I might as well do it online right?  I gave my fair share of winks and sent personalized messages when I felt so inclined.   Pretty soon, I received an adequate amount of attention (winks and messages) and began to have fun with the site.  I had three months, I was determined to make the most out of my membership and go on as many dates as possible.

Ummm, Am I Being Punked?

I came across my fair share of weirdos that I wanted absolutely nothing to do with, but apparently I had everything that they wanted to do with.  After receiving messages from the following men I started to question if I’d chosen the right online dating site.

Mr. Broken Language – Language Arts was just that, an ART.  This was one of my favorite classes in grade school, but I can’t say the same for this dude:

Broken Language.  Can you tell me what the actual F*@K this man is talking about?
Can you tell me what the actual F*@K this man is talking about? (enlarge the pic to view run on sentences and other egregious grammatical errors).

The Serial Killer – I don’t care what anyone says, this man is a serial killer (he just hasn’t been caught yet).

I don't care what anyone says, this man is a serial killer and his pictures scared the HELL out of me.  So much so, that I block him.
His pictures scared the HELL out of me. So much so, that I blocked him.

The Teenager – Word, you can join match.com at the tender age of sixteen? I didn’t know that!  I want you to pay extra close attention to his attire; the jersey, distressed and juvenile jeans, gaudy necklace, watch, and last but not least the bane of my existence – the selfie shot (clearly in the dressing room of a department store).

Word?  You can join match even if your under eighteen?  This "man" is clearly one of the BOYS that Kelis was talking about.
This must be one of the boys that Kelis was talking about.

Trinidad James – “Gold all in my chain.  Gold all in my rang (yes, rang, not ring).  Gold all in my watch.  Don’t believe me just watch.”  What? You’ve never heard that incredibly “rachet” (<– peep the meaning of this slang word if you’re not familiar: http://www.urbandictionary.com/define.php?term=ratchet) song?  Trinidad James is a Trinidadian born rapper with a busted “rack” of teeth (covered in yellow gold caps) that came out with an incredibly catchy song called “All Gold Everything” about a year ago.  While  this song is catchy, it’s also very ignorant (click here to watch the video then accept my humble apologies in advance for subjecting you to eye/ear sore: http://www.youtube.com/watch?v=NK2FqPNIT_U).

His twin, a Summit Security Guard, lurks on match.com and he sent me a message to let me know that I’d caught his eye.

What is that on his head? It looks like the hat that Peter Pan wore when he went back to Never Never Land.
What is that on his head? It looks like the hat that Peter Pan wore when he went back to Never Never Land.
Why is this man wearing a  WOMEN's charm bracelet?  I didn't include his profile, but I can promise you that writing is not his talent, yet above he dons two, count em', two college rings with pride.
Why is this man wearing a WOMAN’s charm bracelet? I didn’t include his profile, but I can promise you that writing is not his talent, yet above he dons two, count em’, two college rings with pride.
Getting to the Good Part
Now I don’t want you to think that it was all bad, because I experienced more good times than bad on the site.  I went on a few dates and have decided to feature three of my most memorable match.com dates below. 
THe Groupon Don
http://www.groupon.com – A “deal of the day” website featuring discounts on a variety of things

The “Groupon Don” (TGD) was the first dude that I’d gone out with from the site.   Before I get into our date, I will describe the series of events that led up to it.  TGD reached out to me first by sending me a message.  I liked what I read so I returned a message to his inbox.  We exchanged messages about 3x before he asked for my phone number.  I enjoyed our exchanges thus far, so I obliged and gave him my contact information.   It was refreshing to speak to someone for about two hours with no awkward pauses in between.  He was intelligent, funny, sarcastic (I love and appreciate sarcasm because I’m very sarcastic), and attractive.  We’d decided to meet in person that weekend.

I’d expressed my appreciation for surprises during one of our exchanges, so he planned accordingly.  I was told that our first date would be a scavenger hunt around Greenwich Village.  Dope right?  I appreciated the originality and adventure of the date idea. Once I agreed to the date you already know what I was thinking, what the heck was I going to wear?  I wanted to keep it sporty chic since I knew that our date would include a lot of walking.  I wore sleek suede black wedge sneakers, fitted black jeans, a denim shirt, and a camo jacket.

We met on a Saturday morning (around 11:00 am) on West 8th and Christopher.  I was early and hadn’t eaten breakfast yet so I went to the Dunkin’ Donuts that I’d spied and purchased a vanilla latte for myself and a green tea for him (he was getting over a cold, I figured he would appreciate that).  I received a phone call as I was purchasing the hot beverages and learned that he was looking for me.  After informing him of my location he made his way to me and we met for the first time as I was exited the doughnut/coffeehouse chain.

To my pleasant surprise he looked exactly like the pictures that he’d posted on match.  Tall (approximately 6’2″), dark (milk chocolate complexion – my personal preference), and stylish (he was clad in jeans, a sweater, and cognac colored leather shoes).  I was pleased.  We embraced; the hug felt weird (he was the first man I’d hugged since my break up), but it also felt natural (I wasn’t uncomfortable around him).  We walked to a nearby park to engage in conversation, finish our drinks, and to prepare for the scavenger hunt.

The hunt was fun, we answered a series of trivial questions, learned new facts about the neighborhood, tried on hats, took pictures, had brunch, went to a tea and coffee shop, went to a garden, went to a church, and to a flower shop (where he was instructed to buy me my favorite flower (I happen to have two so he bought both; an orchid and a calla lilly).

All and all I would say that the date was cool, but towards the end it began to drag.  I felt as if the conversation was running dry and I was no longer interested in forcing one.  We ended the evening around 5ish, as we both had plans that evening.  He walked me to my train station and we bid adieu by giving a hug to each other.  That was fine with me because I’m a bit old-fashioned; I’m not one to kiss on the first date usually unless I feel an insane connection.

The date ended with overwhelming ambiguity (on my end at least); I wasn’t sure if I like him, wasn’t sure if he liked me, wasn’t sure if I wanted to see him again, and I wasn’t sure if he wanted to see me again.  I did what most women do when they’re confused about men – call another woman!   The consensus among my girlfriends was this he seemed to be a nice guy and that I needed to not over think things too much.  So I did just that, I stopped over thinking things and he reached out to me the following day to express his interest in another date.  I agreed, not with excitement, but more with curiosity.  I wanted to know if our next date would erase any uncertainty that I had for him.

He’d arranged our second date as well – dinner and dancing.  We met at Hotel Chantelle (http://hotelchantelle.com/), a restaurant in the Lower East Side (LES) section of Manhattan on a Saturday night (a week after our first date).  This time around wanted to spice it up a little so I wore a black peplum skirt, a white camisole, a royal blue (my favorite color) blazer, and black leather booties.  For accessories, I wore red matte lipstick, pearl studs, and a cameo pin on my left lapel.

Since I arrived at the location first (via cab), I was able to see him as he made his way to me on foot.  He was dressed in a black suit about two sizes too big; the suit “wore him”.   I don’t think there’s anything more unattractive than a man who lets his clothing “wear him”.  We embraced in a hug and respective kisses on the cheeks.  I placed my arm in the crook of his arm and we made our way upstairs onto the roof (as this is where the dining section was located).

We were greeted by the hostess and were immediately placed at our table where we dined by candlelight to top 40’s music.   Once the waitress made her way over to us I felt the need to apologize to TGD for my desire to order a glass of wine.  You see, he didn’t drink.  He’s never consumed alcohol and didn’t care to.  After placing my appetizer and drink order (I opted for a chilled glass of Sauvignon Blanc), I noticed that he’d picked up his blackberry.  I gave him a five second courtesy before asking him to politely put his phone away, as I assumed he was checking his work phone for business.  Wrong.  To my dismay and SHOCK, he was checking something else.  I was informed that my meal included two drinks (wine or mixed cocktail).  He then proceeded to show me his phone on which he was reviewing the Groupon coupon he had for our date there.

Tacky, very tacky.  To be honest, I wasn’t mad that he’d used the coupon, I was mad that he showed it to me.  Why not keep that to yourself?  I immediately thought about our first date; was that a Groupon inspired date too?

The conversation over dinner dragged and he began to bore me.  He suggested dancing and I respectfully declined.  I didn’t care to dance to top 40’s music with the young crowd – a predimoniately early 20’s crowd.

We left the establishment and made our way to his car.  I’d like to tell you that he took me home, but he didn’t.  He suggested dancing in the lounge of  Red Rooster in Harlem, Ginny’s Supper Club (http://www.ginnyssupperclub.com/), so I went.  Why rush home on a Saturday night right?

I’d like to tell you that I had a ball with him, but I didn’t. We danced for about 30 minutes as I watched his shirt change from light grey to dark grey.  His profuse sweating changed the color of his shirt and disgusted me in the process.  YUCK, where was his undershirt to absorb this sweat?  He refused the napkins that I’d offered to him to sop up his sweat so I knew that I was done.  I no longer wanted to dance next to a sweaty dude and suggested that we head out.

We made it back to Brooklyn in no time at all and ended the night.  He was a gentleman; he walked me to the bottom of my brownstone steps and we hugged.  I think we both knew that we would never see each other again and I was okay with that.  I didn’t feel that there was enough chemistry to go out on another date with him.

Thankfully, my weekend didn’t end on a bad note – I had another date scheduled for the following evening with Mr. Nice Guy.Mr-Nice-Guy

Mr. Nice Guy (MNG) reached out to me earlier in the week  by sending me a message.  As with TGD, MNG requested my phone number after we’d exchanged a few messages.  Our first conversation was a brief one, approximately 30 minutes. Even though it was brief, I enjoyed every minute of it.  We had quite a bit in common; great sense of humor, a shared appreciation for various genres of music, an adventure.

After engaging in another conversation the following evening, we’d decided to meet for dinner that Sunday in Brooklyn.  I suggested Peaches (http://www.bcrestaurantgroup.com/peaches) in Stuyvesant Heights as it was less than 10 minutes from my place and I enjoyed the food there.

He arrived around 6:00 pm that evening and called me to let me know he’d done so.  I went downstairs to greet him with much excitement as I was curious to know if the reciprocated chemistry we’d experienced on the phone would be experienced in person. As I made my way across the street as he stepped out of his car.  I learned something in that instance, men that indulge in online dating lie about their height (unless 6’0″ or taller).  MNG’s profile indicated that he was 5’10”, but I think he was more 5’8″, 5’9″.  No biggie, but not really my ideal height (as I’m 5’7″ and wear 3″ or higher heels on most days).  He was dressed in jeans, a burgundy collared polo style shirt, and shoes that tied the outfit together nicely.  I was clad in olive green cigarette pants, gold-capped flat black leather shoes, a cream blouse, a black boyfriend blazer, and a taupe and black cheetah print scarf.  Again, I wore my red matte lipstick (because I love it and feel like it makes just about every outfit pop), along with complementing gold studs.

After embracing in a hug, he opened my door (very gentleman like) then made his way around to the driver’s side.  We enjoyed conversation en route to the restaurant and as we dined.  The jokes were abundant, the food was delicious, and the vibe was chill – I couldn’t ask for more.

After dinner we went next door to the lounge/bar of Peaches, to continue our conversation over libations as neither one of us wanted the night to end.  At around 12:00 am, the bartender announced  “last call” and we made our way to his car, which was parked across the street.   He drove me home and we chatted for about an hour while parked outside.  You would think that I gave him the conventional kiss goodnight, but I didn’t.  He walked me to my door, we hugged, and I gave him a kiss on the cheek.  The chemistry was definitely there, but I didn’t feel the urge to kiss him on his lips.

We exchanged text messages and chatted on the phone for the rest of the week, but it didn’t lead anywhere.  I could tell that MNG was very into him, but I can’t say that those feelings were felt on my end.  He was cool, stylish, attractive, funny, and intelligent, but I was wary.  I think that I was afraid, afraid that I’d met someone who was of substance  and who wanted something serious.  Despite joining the dating site, I realized that I wasn’t actually ready for something serious, it was too soon after my breakup to fathom being vulnerable with another man.

MNG tried to arrange another date, but I was always “busy”.  Pretty soon he got the hint and stopped reaching out.  I feel terrible for the way that things ended, but I didn’t want to waste his time or mine; I wasn’t ready to give him what he wanted.

About a week later I received a message from Mr. Movember.  What is “Movember” you might ask?  It’s an annual event (that takes place in November) in which participants (typically men) grow mustaches to raise awareness for an array for men’s health issues.

I don’t recall the exact day that he reached out to me, but I do recall the hearty sense of humor that he had.  He had a thing for women with natural hair and made it a point to let me know this.  Flattery will get a man everywhere!  Again, after exchanging messages for some time, we took our conversation offline and had our first talk on a Sunday.  The reason I know this is because I missed my favorite show (The Walking Dead) and didn’t even care.  The conversation was five hours long and there were never any moments of awkward silence.

To say that I enjoyed it was an understatement.  I wanted to engage in conversation again, so we did the following evening.  Again, another long discussion; this time approximately two hours.  Needless to say I was anxious to meet the man that could not only hold my interest for so long on the phone, but who could also crack me up hysterically in the process.  I suggested we meet that week and made plans to meet that Thursday in Union Square at The Coffee Shop (http://thecoffeeshopnyc.com/).

Since this was an after work date I was somewhat professional.  I wore black fitted jeans, black leather knee high 3″ boots, a chartreuse colored blazer, a white blouse, and an antique gold colored bib necklace.  I’d reached the diner first, so I walked around a bit to waste time.  Once he made it, he phoned me to announce his arrival.  We stayed on the phone until I crossed the street and we made eye contact.  Again, he was shorter than I’d expected (about 5’8″), but it was cool.  He warned me in advance that he was participating in Movember, but I didn’t expect to meet him for the first time with such a 70′ porn/Magnum PI/child molester stache’.  After embracing in a hug, we made our way into the restaurant.

Instead of being seated, we opted to visit the lounge located on the lower level of The Coffee Shop.  We stumbled upon a salsa dancing class and crashed.  After a quick one-two step, we made our way upstairs to enjoy conversation over food and drinks. Pretty soon I’d forgotten about his larger than life mustache and enjoyed the effortless conversation and laughter.

After about an hour, we decided to head back downstairs to the lower level to chill in the lounge, listen to music and to continue to get to know each other.  The class was still taking place so we sat down on one of the many comfortable cushions and continued to talk.  Once again, we closed the establishment down (as I did with MNG).

The lights came on and we made our way outside to the nearest train station.  We exchanged hugs and parted ways.  I can’t explain it, but I knew it.  I knew that I would never see Mr. Movember again.

Sometimes you just feel a spark.  While I felt it, it wasn’t reciprocated and I could tell by the hug that I  received – it felt platonic.  As if that wasn’t enough, our follow up conversation in the wee hours of the morning (as I walked from the train station to my apartment) solidified my thoughts.  He seemed distant, disconnected, or removed.

I can take a hint, but Mr. Movember confused me.  We engaged in a few more lengthy conversations via phone over the course of the week, but I never received an invitation for another date.  I was cool with that, but I wanted to know why, so I asked.  As expected, he informed me that he felt more of a friend vibe than a romantic one.  Ah well, you win some and you lose some.  Despite the lack of a love connection we continue to remain in contact on a friendly basis because I’m all about keeping in touch with cool people.

So here I am.  Three months after my 1st three-month membership with match.com.  Since my experience was more positive than negative, I’ve decided to resume with another cycle of online dating next month.  I’ve narrowed the sites down to match.com, blackpeoplemeet.com, and e-harmony.com.  I’m looking forward to going out on more dates, having new experiences, and getting to know cool people.   Stay tuned!

Until next time friends!

– PenniePenz


17 thoughts on “Mis-Match.com

      1. question? Would you like to be apart of the hope series on my blog?
        Operation: Happy happy Joy Joy, takes to the streets of Manhattan to ask random people what gives them hope.

        After being diagnosed with cancer, I decided to start this project. I could either interview you via google hangout or you could just record yourself via iphone or ipad and answer a few questions. You have a fantastic sense of humor and we could use that over in cancerville.

  1. Lol. Enjoyed reading it. Lol. Really though with a groupon. I had one guy literally break down the gas mileage to pick me up for a date. If you can’t afford the gas to get me then you don’t need to go on any dates. Needless to say we never went out and I never saw him again. Lol.

    1. Haha, thanks Jess! I know, these dudes have no shame in their game apparently. WOW, what a cheap jerk. He really tried to talk to you about gas. Tacky, just tacky! I wouldn’t have gone out with him again either! Good call 🙂

  2. Very interesting episodes. I have yet to get my feet wet with online dating, depsite having a few profiles. My issues have been similar to yours, except no one has fit a profile that is half way dateable. But darn it, I paid for How About We and I’m going to need at least a meal out of it 🙂

    Anyways… great post… I enjoyed reading. Thanks for sharing.

    1. Let’s get it Neish! Let’s get all the dates we can out of it and have fun with it as Taryn suggests! I truly have no hopes this time around, but am looking forward to the experience :). In the meantime, thanks for reading – let’s keep each other motivated!

  3. This time is gonna be different! I can feel it! Have fun with it and if more comes great and if not, I’m sure I’ll be laughing from the stories!

  4. Funny, girlfriend. Never tried online dating….I know my luck and since I have no desire to be on the six o’clock news, I will take my chances with meeting men the old fashion way. Lol

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