Remember Mr. Charlestonsurf, the self-proclaimed southern gentleman looking for a classy and funny girl to settle down with? (If not, read about him here, under Potential #2). Well after almost two weeks of texting we finally went on a date, and let me tell you: this boy has a skewed definition of what it means to be a “southern gentleman”.
Florida, circa 1 week prior to date:
Charleston and I had been playing Words With Friends (a mobile version of Scrabble) ever since we had exchanged phone numbers on OkCupid. Between turns, we would engage in slightly flirtatious back-and-forth banter in the game’s chat area.This opens the door to casual texting and soon we are each other several times an hour. Gross. But in my defense, I was stuck out in Boca Raton, FL with no TV, no internet (aside from my phone), and a bunch of old people. Damn right I was going to text anyone who’d listen about the colour of my wallpaper and the taste of my lunch.
Anyway, at some point our conversation got a little more flirtatious. I didn’t really mean for the following conversation to go down that route either. It just…happened.
me (in response to him asking what I was doing, or something): “…just put em to sleep. It may be bath and wine time.”
Him: “Add some bubbles, and you have a party!”
Me: “Sounds like a lame party unless I add something else…I’m gonna be a good girl and do yoga pre-bath.”
Him: “Haha, what else would you add, whiskey?”
Me: “Oh, ummmmm…no…”
Him: “Just kidding… You clearly need someone to wash your back”
Me: “That’s closer to what I was thinking.”
Him: “Naughty girl, you’ll wake the kids;)” (Note to readers: I do not have kids. I am a nanny and was away with the family babysitting, FYI.)
Me: “It’s a big house!”
Him: “Well then, no one will miss one of those cucumbers, have some fun!”
GROSS! GAG! ACK! EEK! ABORT! The fact that he went right for the image of me with a cucumber when he thought of me masturbating makes me think he’d be a lousy lover. He can have whatever image of me in his head that he wants, but all I heard when he said ‘cucumber’ was “YOU NEED A PENIS TO HAVE A GOOD TIME! I HAVE A PENIS! PICK ME!”
Me: “Hey I wasn’t saying I was going to go down the naughty road—only saying that your definition of what made a party was missing something and sounded lame!”
Him: “It’s ok to go down the naughty road from time to time, it’s healthy!”
“And yes, I was missing an ingredient, glad you caught that.”
“I was going for funny, but that sounded weird. New subject: Florida. How is it?”
Anyway, it wasn’t a disastrous text exchange, but it wasn’t great either. I decide that until we meet, our texting will remain squeaky clean. Then, I got a sunburn and told him about it. I was trying to be cute, and at one point:
I said: “My poor burned tuckus! (how do you spell that??)”
Him: “No clue, but a pic is required!”
Me: “Ha. I admire your attempt.”
Him: “Oh come on, be a sport.”
Now I know what you’re thinking. If I sent a freaking picture I am out of my mind bat-shit crazy. But being delusional, I thought I kinda liked this guy, despite never having met him. I was also bored out of my mind. And my last excuse is that my ass looked REALLY good despite being a shade of red that I am only used to seeing after a good flogging. Oh, and I’m also a
whore—I mean exhibitionist whore.
So I sent a picture. It was not that risque at all: it didn’t show my face, and I had my knickers on (though slightly hiked up to show the burn lines), and a bare back. I just spent 10 minutes debating whether I should post it here, but I am (slowly) LEARNING HOW TO SELECTIVELY CENSOR MYSELF. It’s hard. Because in my eyes: you have an ass + I have an ass +we all have an ass = why cover up? Shake shake shake it.
The good news is that I didn’t send any additional pictures, despite his requests for more provocative follow-ups. Not because I have too much class or dignity, but because I was reminded that he is only 5’7″, and based on the handful of pictures on OkCupid, I wasn’t sure whether I would find him attractive in real life. The last thing I needed was to give him the impression that I couldn’t wait to
meet him go home with him, which I’m sure he had already convinced himself.
Friday, circa one week later. Date night:
I had just spent 5 magnificent days in a row with Gregory, and my excitement for meeting Charleston had waned significantly. I realize as I am begrudgingly getting ready that if by some miracle or severe lack of judgment I decide to sleep with Charleston tonight, I will have slept with two people within a 12 hour period— which save for threesomes and orgies, would be a first for me.
Since he’s new in town, I’m in charge of finding our date spot. He suggests I pick a place in Carroll Gardens, which is coincidentally where he lives and is completely out of my way. I tell him I’ll pick a neutral spot in the city, and I make a mental note of his somewhat rude let’s-keep-the-date-as-close-to-my-bed-as-possible suggestion.
Someone on facebook recommends Raines Law Room, which is ultimately where I decide on. Our date is originally scheduled for 9, but I find myself characteristically running late and postpone our meeting time; first to 9:30, and then to 9:45, which I am *gasp* on time for. I have on a very low-cut,nearly backless black top, stuck in place by strategically placed strips of body tape, a black high-waisted bubble skirt, a cropped blazer, and black tights. I also don a pair of 3.5″ heels, which leaves me standing one inch taller than my date. Dumb move.
So I’m walking down 17th street, simultaneously trying to find the bar and get excited for the date. Both are proving difficult to do. The next thing I know, he is 5 feet away and walking towards me. I’m a little thrown off because I anticipated meeting him in the bar—not on the street with my headphones in and coat on. He informs me that the bar has a 90 minute wait time, which is why he had been waiting for me outside. We obviously choose to go elsewhere.
The first thing I notice about him is that he is wearing a navy blue fleece, with a small company logo across the chest. I’m all for men dressing casual, and I sometimes even have a thing for blue-collar casual, so while his outfit isn’t an immediate turn off, I am secretly grateful for the long wait at Raines Law Room, which is definitely more upscale than down. The second thing I notice is that he is actually relatively cute. Not sexy–but cute. Adorable even. Maybe it’s his pint size. When he speaks his mouth does this weird thing that I can’t explain—but if you saw him talking, but couldn’t hear him, you would probably think he had a lisp. Luckily for him, I have a thing for weird mouths and minor lisps.
I have to pee, so we duck into the first bar we see. It’s a relatively empty dive, which I like, but I am definitely over dressed. We grab seats at the bar, and he orders me a Stella while I go pee. Now here’s the thing: I hadn’t planned on taking off my blazer to reveal the full nature of my extremely low cut and backless shirt unless things were going really, really well. But the bar is hot. Even our beers are warm, and I can feel beads of sweat accumulating on my forehead. If I don’t take my jacket off, my bangs will soon absorb my sweat and clump up across my forehead, and I won’t carry it nearly as well as Jessica Biel:
So while he is ordering us our second beers, I try my best to casually remove my jacket, thinking maybe he won’t even notice. Instantly, he turns and stares at
me my tits and goes, “taking off your clothes already?”. I try and defend my sad excuse of a shirt by explaining to him how hot it is in the bar, and I remind him that it’s Canadian blood that flows through my veins, not Southern blood like his.
As far as conversation goes, we are doing just OK. There aren’t many awkward silences, but mostly because I am working very hard at filling them up the moment I sense them. He sold himself online as being someone who always makes people laugh, but so far I haven’t seen even a glimpse of a funny side (though he is doing a good job laughing at my jokes and stories). We stupidly break all the rules and somehow start talking politics. Fortunately (and perhaps surprisingly), we’re on the same page when it comes to gay marriage and Republicans, but our conversation does get heavier than I’d like for a first date.
At one point he starts explaining to me that the reason he is still single at the age of 30 (not that I asked) is because he would rather be single than lower his standards. But he is saying it in such a way that insinuates that I am up to his ridiculously high standards and should thereby be flattered. Then he starts explaining that his mom is kind of neurotic and is always on his case about when he is going to get married and have kids—but he is saying it with a sick sense of pride–as if I am somehow supposed to find this appealing. In reality, I’ve started to sweat again, and I’m eying the shelves of hard liquor thinking it may be time for a shot. Then he says, “for instance, let’s say you and I are dating, and I tell my mom. She’ll expect me to bring you to South Carolina the next day. Even if you and I just went on a couple of dates, if my mom found out she would almost instantly find you on facebook and be writing all over your wall, inviting you to South Carolina and asking you all sorts of questions.”
Let me take this moment to explain how much I despise “momma’s boys”. It’s great if you have a mother whom you love and cherish and respect. But if you are a grown man and you are still being mothered as though you were a child, there is little redemption left for you as far as turning me on goes.
I have to pee again, and as I walk away from the bar I can feel him staring at my very naked back. When I return, I slide back onto my bar stool, and his hand simultaneously slides across my upper back. What happens next is difficult to explain, and even typing it makes me red-in-the-face for his sake.
He says (while caressing my back), “your skin is so soft…”
I see him lean in for a kiss as he says what can only be labeled as the WORST LINE EVER,
“…Are your lips just as soft?”
I instantly grab my beer and block my mouth with it. I let out an uncomfortable giggle and I’m all, ” NOPE! My lips are actually SUPER chapped and gross at the moment. Super, super chapped. Cracked and bleeding actually. Must be the weather.”
Let it be known that were it not for that line, I would not necessarily be opposed to kissing him—at some point. But we were about 30 minutes into our date I was completely caught off guard and appalled by his tactic.
Instead of taking the blow to his ego and accepting the fact that I do not want to kiss him, Charleston persists, leaning further into my beer-face-shield and saying, “What are you talking about? They look pretty soft to me“. I must make some sort of disgusted face before taking another sip of my beer, because he follows up with, “no? Really? I’m getting shot down? Ouch...”. He is still leaning towards me though, so through pursed lips and a half awkward smile I respond, “yeah…..I mean… I dunno that was quite the line…and it’s a little early into the date…”
AND THEN HOMEBOY KISSES ME!!!!!!! He straight up moves my beer from my face, and says “come on…” and kisses me! The kiss lasts maybe 3 seconds, which is 3 seconds too long. He’s not a bad kisser but I am in shock that his lips somehow ended up on mine despite my obvious lack of enthusiasm.
I think I’ve blocked out exactly how the kiss ended/how we moved forward with the date, but rest assured it was awkward. Shortly after, we finish our beers, and he closes his tab. I don’t offer him any cash, because the tab was something like $20 and we are heading to another bar so I figure I can offer to pay for our drinks there. We hop in a cab and head further downtown to a bar with decent pool tables. I pay for our $11 cab. I wouldn’t be updating you with all this nonsense about who paid for what if it wasn’t important, so hang on and make note.
The bar is crowded (with NYU students) so Charleston suggests I try and order our beers, insinuating I’ll have better luck grabbing the attention of the male bartender than he would. Sure enough, I manage to order us drinks in a few moments time, and as I am removing money from my wallet I see Charleston pulling out his credit card. I tell him not to worry about it, and start to hand the bartender my cash. Charleston pulls my hand back and insists on starting a tab. He goes, “No seriously, just let me start a tab. I only have like $6 cash on me. I mean, I have a lot of money in the bank—but just don’t have cash on me, so please let me start a tab.” Attention: why would you ever go on a date with $6 cash????? That’s ridiculous!!!! I also don’t need to hear whether or not you ‘have a lot of money in the bank’. Anyway, I let him start a tab and we head to the back to play pool.
There are three pool tables, one of which is open. I win the first game, and according to my notes (yes, I make notes) he made some sort of comparison between pool and sex. I don’t recall what the comparison was, but I’m certain it was ridiculous. At one point, this extremely drunken girl sprawls herself across the pool table across from us by way of a back bend. She lifts one leg up and reveals a whole lot of thigh and her entire thong-wearing ass, none of which is particularly flattering. The bouncer has to come and ask her to remove herself from the pool table, and potentially the bar. Charleston and I are watching her and I make some sort of “oh my…” remark, because this girl is making a fool of herself, but Charleston gives her a run for her money by saying, “See, now if you ever behaved that slutty I would not be OK with it.” Ew!! Who does this guy think that he is? First of all, it would take a whole lot of date rape for me to be ass-out in a bar smothered in NYU students. Secondly, why is he under the impression that I care what behaviour he finds tolerable or not? If I want to take my clothes off, I’ll take my clothes off.
Two guys come along and ask us if we want to play doubles with them, which we agree to. One of these guys is GORGEOUS, and we totally make eyes at each other throughout the game. His less-than-gorgeous friend asks Charleston how he knows me, and I get the impression he is asking because the delicious looking guy is curious whether or not I am on a date. WHAT DOES CHARLESTON TELL THEM YOU ASK???
“Oh, we’re married!”
“Oh really? For how long?”, our opponents ask.
“Oh, I think about a year and a half now–right honey?” He slides his hand across my naked back as I bend over the pool table to take my shot and pretend that life is not happening as it is. I don’t know WHAT to say. The whole “pretending we are married when we are not” game COULD potentially be fun (? ) but I do NOT want to pretend to be married to Charleston, especially when I’ve already pictured my hot opponent naked at least 6 times. Also, if I ever play that game it’s because I hate the idea of marriage, and I am playing it with someone who feels the same way, and we are playing it for the pure purpose of fucking with people for shits and giggles. However, I get the impression that Charleston is living out this sick fantasy of me being his trophy wife, and I’m afraid that if I go along with it he may actually become delusional and think it to be true. I mean, I’m half anticipating his god damn mother to walk into the bar and welcome me into the family any minute. So I simply roll my eyes, and answer “…yeah, one and a half years too long” and make my shot. Then I ask him to go and get everyone another round of beer. While he is gone, the hot guy asks where we went on our honeymoon. I immediately blurt out, “I am not married to that man. This is our first date and probably our last.” This leads to a somewhat fun game when Charleston returns, because our opponents continue to have him elaborate and on this made up life he has created, until 30 minutes later Charleston confesses that we are not actually married. He’s expecting this big “OH MAN! YOU HAD US FOOLED!” reaction, so the expression on his face is pretty priceless when we all reveal that I spilled the beans a long time ago, and the joke’s on him.
We win the game but leave the table to our opponents. We head to the bar to close his tab, and somehow I agree to have one more beer. It’s weird: despite all his blunders, I’m not having an AWFUL time with him. I know that I probably don’t want to see him again, and I know that we are not a good ‘match’, but I surprisingly enjoy his company on some level, and I love beer and don’t feel ready to go home quite just yet.
It’s during this time while we are sitting at the bar that Charleston tries to get me to go home with him. I decline, telling him I’d like to spend the night in my own bed. He then asks if he can come over to my place. No Charleston, you cannot. Perhaps he is trying to save face, but he makes a comment along the lines of “don’t worry—you don’t have to sleep with me. We don’t have to do anything. In fact, if you slept with me I would probably lose respect for you anyway. I mean, look– (at this point he pulls out a condom from his pocket to show me)—I never know what’s going to happen, so I’m always prepared, but that doesn’t mean I was or am expecting anything. So why don’t you just come over and cuddle and let me give you a massage.”
Wow. I’m now regretting agreeing to that last beer. Hey Charleston–thanks for clarifying that I “don’t have to” sleep with you; I was really confused about that. And thanks for showing me the condom. Without it, I totally would have had unprotected sex with you. Here’s what I say:
“Hey, I’m not trying to play some sort of coy I-don’t-go-home-with-people-on-the-first-date card here. If I want to sleep with someone, I sleep with them. Life’s too short to live it any other way. I’m not declining your invitation for fear of you losing respect for me, but for lack of desire. I’m not feeling those feelings toward you at the moment and would prefer to go home and sleep alone.”
I’m kind of proud of myself because I often struggle at turning people down (hence, why he has managed to sneak a few kisses in, and why the disaster that as Pizza Breath ever existed). I’m not suggesting that I normally end up going home with people even when I don’t want to, but I usually decline by making indirect and less-than-honest excuses along the lines of I-have-to-be-up-at-the-crack-of-dawn-so-I-have-to-go-home. So this is a step forward in the right direction.
Surprisingly, he asks if I’d have one more beer with him. I tell him that I think it’s best if we settle up and head our separate directions. So get this: He asks the bartender for the check, and as he is waiting he says to me, “Sheesh, you’re quite the expensive date.” Now if he was being SARCASTIC this would be OK. I mean, we have spent our night between two dive bars, drinking nothing but beer! But he is DEAD SERIOUS, and actually sounds mildly annoyed. This is especially ridiculous considering that when the bartender brings our check over, the grand total is $24!!!!!! MAYBE, he was anticipating it being a lot more, but even so, don’t fucking tell me I am an expensive date when I’ve gallivanted around a bar with you pretending to be my husband. I don’t think he realizes that I’ve seen the total on the check, and I hand him a $20 bill since he is blatantly annoyed at what an expensive date this has been. HE ACCEPTS THE $20.
Let’s do some math:
tab at first bar: $20 (plus tip) =$25?; paid for by him.
taxi cab ride: $11 (plus tip) = $13; paid for by me.
tab at second bar: $24 (plus tip) = $30? = $20 paid by me, $10 paid for by him.
Total money spent by me: $33.
Total money spent by him: $35.
Look. I have no problem paying for things on a date. On a first date however, I do prefer to be “taken out”—and call me crazy, but I anticipated that someone who labels themselves a “southern gentleman” who “knows how to treat a lady” would pick up the tab, sans complaints. Then again, I also didn’t anticipate him trying so hard to get me to go home with him. Even so, the problem lies not in the fact that the date ended with us each spending a similar amount of money, but in him making a big deal over it and acting as though he spent a lot more money than I did.
Anyway, Charleston leaves to go and use the bathroom and tells me to wait for him so he can help me get a taxi. I immediately text Gregory, who I have spent a lot of the date thinking about. Literally AS I HIT “send” I get a text from him, telling me that he is thinking about me.
Charleston comes back, and puts me in a cab and I head to Gregory’s and have a wonderful ending to my evening. About 45 minutes after leaving Charleston, I get a text telling me that he had a wonderful time and that we should hang out soon. On Sunday evening, he asks me how the rest of my weekend was. I really MEANT to respond and politely tell him that I wasn’t interested, but I was still having a great time with Gregory and couldn’t be bothered. I’ve received one other text from him since, but luckily, he’s no RALPH, and seems to have gotten the hint.
On another note, I have a date on Thursday night with a girl, who I spoke to a long time ago on OkCupid, but for whatever reason our communication ended and just started up again. I was super excited about her then, and I am super excited about her now. I told her that if she keeps me out past midnight, she’ll have to sing Happy Birthday to me–since Friday is my 26th birthday. Eeps! This led to a slew of flirtatious texts involving the possibility of coffee on Friday morning should the date go really well…and I’m all giddy like a school girl.