Mr. Tennis, Date #2 (and last)

Mr. Tennis originally invited me out for dinner, and when it comes to the day of our 2nd date, he texts, "Want to watch a movie at my place?" In no mood to have sex with him, I decline. After a couple more attempts, he finally gives up. We decide to meet at one of my favorite restaurants that I used go to with my ex. Tennis is already waiting for me when I arrive, he's somewhat grumpy because he just worked out and is starving. I don't stand for grumpiness, so I give him the cold shoulder. He notices and then tells me I look very pretty. Yes, this is about as mature as you can get with a 24-year-old.

Our dinner convo is mostly bland sprinkled with a few flirtatious remarks that my vagina remotely responds to. When the bill comes, I take out some money and Tennis says, "No, my treat. This is your birthday dinner." I inch my money towards him a little bit more, and he takes it. Well, I guess it's not my birthday dinner anymore!

We leave the restaurant and Tennis puts his arms around me and tries to kiss me on the lips. I turn my head and end up with a sloppy kiss on my cheek/eye region. It's all a little juvenile and awkward, and to top it off, we decide to go to McDonald's for ice cream. When I'm with Mr. Tennis, I kind of feel like it's a school day in college. We're hanging out, having light conversation, and have to get up for class the next morning. I already knew that nothing would develop in this relationship, and on this second date, I have confirmed that feeling. I hug Tennis and catch a cab to go home. This will most definitely be our last date.

Another one...chopped!

Reacher or Settler?

I was watching How I Met Your Mother tonight and the topic was about the "Reacher" vs. the "Settler." The theory that there's both in a relationship, where the "Reacher" is dating someone out of their league and the "Settler" is settling for someone below their league. Although I 100% agree with the theory, I also wonder if the Reacher vs. Settler is based on reality or mentality. If it's reality, then the most objective person would be able to pick out the Reacher or the Settler in a couple. However, if it's mentality, then it's all about the dynamic of the relationship.

For example, I can't make myself crazy about Mr. Ireland because I feel like he's the Reacher in this courtship. For some reason, he's not as physically attractive or as witty as I think I am. Pretty cocky of me, right? But as a result, I am not as attentive to him as I should be and I don't feel the need to return any of his phone calls or texts. And what happens in return? He keeps trying, because now he's put in that Reacher position.

On the other hand, there's my situation with Mr. Sporting Goods. I feel that I am the Reacher because for some reason, I find him so incredibly attractive with an amazing pedigree. And as a result, I give him my undivided attention and I agonize over his calls and texts. And what happens in return? I am always available for him and I freely spill my feelings about him.

The point is, I think a successfully played game in dating is to be the Reacher in reality but Settler in mentality. It'll keep both parties wanting more. Now, saying it is much better than doing it. Good luck to us all!

6th Date w/ Mr. Sporting Goods

The day after our 5th date, Sporting Goods comes over. I clean the apartment and have plans ready for a great Friday night. Sporting Goods, on the other hand, may not be on the same page. He shows up at my apartment with a book in hand. I ask him why, and he responds, "I figured if you have plans to go out tonight, I would just go to a diner and read." WTF?! Apparently, we have a misunderstanding where he thought we had a sex date. Meaning, he was coming over for a movie and sex. He claims this is what I told him the night before when I was wasted. I give SG the benefit of the doubt and we go have dinner together. There's still a little bit of tension and I'm not sure how I'm suppose to feel. At one point, I ask him what he wants in life. And he responds, "to lead an unselfish life, because I've been so selfish the past 3 years." I like the answer, it means he's wanting to change. I feel better and we go back to my apartment to fuck.

I guess you can't have 2 amazing dates in a row, but at least we got over our first misunderstanding. Now, about that book...seriously?!

5th Date w/ Mr. Sporting Goods

After getting into a panic attack from not being asked out by Mr. Sporting Goods more than 5 days after our last date, he finally texts to ask me out for Thursday. Although there has been communication in those 5 days, I feel like I went through a transformation. I am falling hard for SG and I need to pull back, because it is not good to have someone affect me like this. So, going into our 5th date, my mindset is to 1) control the situation, 2) gain back the power and 3) not sleep with him. I also wear my tightest and shortest little black dress with high heel boots. I suggest a place to meet and I show up early so it would throw him off a little bit (since he's always the one waiting for me). SG shows up and seems tired from a long day's work, but also happy to see me. As we're catching up, I notice him blatantly checking me out. In our first few minutes of silence, he turns to me and says, "You look good." Ah, the outfit works like a charm every time. I am thrilled on the inside but I keep my cool on the outside with the response, "Oh, I had a dinner thing earlier." SG looks disappointed and says, "So, it wasn't for me." For the next 4 hours, we have some of the best conversation I've ever had on a date. Not only are we feeding off of each other's energy, SG is giving me his undivided attention. It's like we're the only 2 people at the bar. Throughout the night, SG is putting his hands on my legs and periodically holding my hand. SG usually doesn't display PDA like this so I am milking every minute of it. I feel like I'm on my A game and it is the first time I am fully confident that SG is into me. My feelings are then validated when SG asks me to go on a group ski trip with him. I am ecstatic and gladly accept. We close down the bar and the rest is a little fuzzy. I can recall us getting into a cab and SG holding my hand down my block. I tell him that he can't come up and we make out for a long time. He insists on walking me up to my door and in the process, finds Mardi Gras beads randomly and puts them on me. We make out some more in front of my door and I tell him that I want to see him soon. He immediately responds with, "How about tomorrow?" I get to see SG two days in a row? My heart jumps for joy and we kiss good night, for the millionth time.

Best. night. ever.

Mr. Tennis, Date #1

After almost a month after Mr. Tennis canceled on our first date, we finally get to meet up together. I have no expectations because my heart is still settled on Mr. Sporting Goods and mother nature is making her visit this week. I've been driving myself crazy lately because SG hasn't asked me out this week. I've seen him every week that I have been in town so breaking the pattern is also breaking my heart. That is why, I've decided to take on a new distraction of Mr. Tennis.

We decide to meet at my neighborhood bar and I show up early so I could start drinking early. I find Tennis attractive but being that he is almost 5 years younger, I know there is no long term potential with him. Tennis arrives while I'm halfway done with my first margarita. He is as cute as I remembered and also as nervous as I remembered. It's endearing. Tennis has an Abercrombie/frat boy appeal that brings me back to college. I like that he is athletic and clean cut. I think because of his nervous energy, it makes me more confident and assertive. We start talking about all sorts of random things and a couple hours later, Tennis has his arms around me. As I finish my 3rd margarita, I lean into him and we start making out. By the way we are kissing, I know right away that this is just for fun.

Tennis picks up the tab and we head to my apartment. I am feeling happily buzzed so my liquid courage allows me to take control of the situation. I light a candle and push him on to my bed. He's saying all sorts of things that make me feel like I'm in a rap video such as, "baby girl." Tennis grabs my ass, takes off my shirt and tells me that I am pretty. I think that's the magic combination to unlock my inner-whore. I put on some sexy music and start slithering my naked breasts up and down his body. I then grab his cock and start rubbing my nipples on it. Tennis is going crazy. He keeps saying, "Let's fuck" but I know that's not a possibility, so I keep teasing. I even put my tongue on the tip of his penis and circle it around until he tells me he might come. So I stop. What a bitch, right? We tease each other for a good hour or two (hard to tell because it seems like I'm getting more wasted), and I finally give him a hand job to finish him off. We clean each other off and he leaves so he can make it in to work at 8am. I'm relieved that he doesn't sleep over because I feel like I might throw up.

Will I see Tennis again? Sure, for as long as I need a distraction.

4th Date w/ Mr. Sporting Goods

It's only been 3 days since our last date, and I get to see Sporting Goods again. This time, he wants me to come to his hood in Brooklyn. Normally, I'm opposed to dating anyone outside of Manhattan, but for SG, I'd even consider going to Jersey for him (and thank God he doesn't live in Jersey). I dress a little more casual this time in T-shirt and jeans and meet SG at a trendy restaurant in Williamsburg. SG is waiting for me at the bar and I am excited to give him a hug. We have a lovely dinner and random conversation. SG picks up the tab again and as we begin to leave, he compliments me on my coat. I always find it fascinating when a guy comments on a girl's fashion. It shows that they're paying extra attention.

We go and grab drinks at a bar nearby and finally go back to his place. This is my first time to his natural habitat and I have played this scenario over and over in my head. On one hand, I picture a filthy frat-like environment with dirty dishes and pubes all over the bathroom floor. On the other hand, I picture a minimalist apartment with very little to comment on. As we pull up to his apartment, I notice a grand luxury high-rise building right by the water. As he opens the door, I am pleasantly surprised by how nice the apartment is. Although he lives with two other guys, the place is spotless. High-end stainless steel appliance, panoramic view of Manhattan with floor-to-ceiling windows, and an over-sized master bedroom with a 5-piece bath (that would be his room). I briefly meet his roommate and SG leads me to his bedroom. He closes the door behind and starts to kiss me. The view from his room is beautiful and the romantic atmosphere sets the perfect mood for our first actual sleepover. An innocent kiss turns into a 5 hour sex romp while listening to his itunes "sex playlist". Let me quickly list all that I can recall:

- 20 second teaser BJ (I'm so proud, I gave a blow job!)

- 5 minute of him going down on me

- Missionary

- Doggy-style

- Me on top

- Him fucking me while I'm hanging on his pull-up bar

- Him fucking me on his bathroom sink

- Him fucking me in his bathtub in complete darkness

- He comes twice!

- 7 condoms

- A shower together

After all this, you'd think I'd be exhausted. But no, I have an urge to talk about us. Why must women always choose the worst times to "talk"? I tell him that tonight there's been a change in dynamic. I ask him if we're just about sex or more than just sex. He tells me that he's glad we're having this conversation and he appreciates open communication. SG then tells me that for him, it's more than just sex. However, he knows he's a distant person. I then confess that I like him a lot and I just want to make sure I don't have the wrong expectations. Still feeling a little bit conflicted, we fall asleep. But, I am excited to find out that he has tomorrow off.

The next morning, we wake up on opposite sides of the bed. I think to myself if I could honestly be with someone who is as distant and as cold as him. I don't want to make the mistake thinking that he could change, because nobody can be changed unless if they want to change. As I lie there, I convince myself to create more distance between us so I don't get hurt. SG then eventually comes over to me and cuddles with me. It feels nice and I have hope again. We talk for a little bit and proceed to have more sex. Afterwards, he makes us some coffee and we eat last night's leftovers as we listen to music. We then go back to his bedroom and watch an episode of "It's Always Sunny in Philadelphia" that he thinks I would love. It's hilarious and we have a good laugh. The good laugh then turns into more fantastic sex. I come and he comes.

We end the sex marathon with long, soapy showers. Afterwards, we talk some more and he thinks we are very similar sexually. It's totally true. As I lotion my naked body in the bathroom, he stops in mid sentence and starts nodding his head. "What are you doing?" SG: "You have a very nice body. I am nodding in admiration." Wow, SG has the capability of saying something that nice? I will take it. It's now about 2pm and I decide I shouldn't linger any longer. I get dressed and SG calls me a cab. He kisses me in the elevator and again before I get in the cab.

I'm falling hard for the tin man whether I like it or not.

Brooklyn and Tennis want in.

I guess the saying is true: when it rains, it pours. Not only do I get a slew of texts from Mr. Brooklyn (remember him?! The 22-year-old baby), but Mr. Tennis also texts wanting to hang out. Brooklyn just wants to fuck despite an abnormal text wishing me a Happy New Year vs. the usual "What's Up?" I haven't thought about him in so long, there's no point in bringing him back anymore. Besides, I should only move up, not down!

As for Mr. Tennis, I'm still remotely interested. And selfishly, I just feel like I need distractions around so I don't think too much of Sporting Goods. So, I respond to his text and we agree on a drink date next week. I don't know what he expects but I don't plan on sleeping with him.

Sporting Goods calls for 4th date!

While normally it takes SG 3-4 days after a date to contact me, this time SG wasted no time. He texted me today with an inside joke from our last date and then ended it with, "Want to hang out Thursday?"

This may not seem like a big deal but hanging out with SG TWICE in one week is a big deal to me. I like to think we're making progress and I'm hoping he'll be able to finally sleep over on Thursday.

Morning sex would take our "involvement with each other" (notice I don't use the word "relationship?") to the next level.

You never know who sees you

The day after my date with Mr. Ireland, I get a message on Facebook from a guy that I had worked with on a short-term project over 2.5 years ago. He writes, "How was the food last night?" A little bewildered, I respond back, "Huh? How did ya know?" He then tells me that he saw me at the restaurant with a guy and didn't want to interrupt because the guy seemed to be talking a lot. I tell him that I was on a first date and he says, "I hope it was a first and last. If I would've known he wasn't your boyfriend, I would've come in and stolen you from him." He then ends the conversation with, "Glad to hear you're no longer with your boyfriend. Let me know if you need a sushi/sake partner sometime."

I never really thought about it before but in city like NYC, it is very likely you could run into people you know. Most of the time, it'd be nice to see a familiar face while on a date, but at the same time, it would not be fun to run into someone else I was dating. In this situation, I somehow became more desirable for this guy who I had only met once and worked with for approx. 8 hours over 2 years ago. But let's say if I had run into Sporting Goods while on my date with Ireland, would SG lose interest or would it make him fight harder?

3rd Date w/ Mr. Sporting Goods

I wish everyday could be as exciting as waiting for today, because I have been dying to see Sporting Goods for the past almost 3 weeks! I get a little more dressy than normal because I want to remind him of what he has been missing all this time. Here's the gist of my look: short t-shirt dress with a low-cut V, tights, and over the knee boots. Also, bouncy bedroom-ready hair. It's still effortless but also not so pedestrian. Although the restaurant is a mere 10 minute walk from my apartment, I hop into a cab because I can't seem to get there fast enough.

I arrive at the restaurant in Union Square and there he is waiting for me. He is insanely hot. He came straight from work so he's in his button down shirt, tie, and pinstripe slacks. It may sound like your usual corporate attire, but trust me, he makes corporate sexy again. SG also got a haircut and it suits him well. I still get nervous when I see him and I can feel my armpits perspiring. It's not cute. I take off my coat and reveal my outfit while wearing his scarf that he left at my apartment last time. The scarf goes perfectly well with my outfit and SG is entertained.

We, of course, talk about our holidays and whatnot. Most of our conversation is witty banter, kind of like an episode of Seinfield. SG likes to throw out hypothetical situations for me to decipher. We also sarcastically analyze all the avant garde artwork around the restaurant. Dinner has been nothing but perfect and I am so happy to be in his company. Beyond happy. It's euphoric. I can acknowledge the fact that I am very infatuated with SG. Whether he feels the same way about me, I can't tell. I must get to the bottom of it tonight.

After dinner, SG kisses me outside the restaurant wants to know if I want to go back to Brooklyn with him. It's 10 degrees outside and I really don't feel like doing the walk of shame tomorrow morning from Brooklyn. So, we get in the cab and I tell the cab driver "2 stops." "Ouch," SG reacts. We get to my place and I ask to get out from his side, he turns to me and asks "Are you really not going to ask me up to your place?" Hahahaha, I pat myself on the back and think "well played." I tell him he can come up, of course.

When we get to my apartment, I make him wait although I know I just want to jump on him. We wait a whole 15 minutes before it's a full-blown make out session. I have missed kissing these lips and being in these arms. The make out session lasts for a really long time, and I love that because I think I could make out with him for days. We then slowly peel off each other's clothes and to solve the sex lighting problem, I light a candle. It's perfect now and I can see SG's amazing manly body. There is nothing little boy about his physique. The awkward and also fun part about having sober sex is that we're both trying to explore each other and understand what we like. It's kind of exciting because with each penetration, it gets better and better. His cock is such a nice size and fits perfectly inside of me. It never fails to hit my G-spot and I orgasm for the first time with him. SG then gets up to take a shower because he claims that he wants to wash off his long day of work. It's a first, but I get it. Ha.

When SG comes back, we go at it again. SG goes down on me for a good 10 minutes and we proceed to go through 4 condoms in the next 3 hours and I orgasm again. I can tell that he is frustrated so I give him a hand job and let him cum on my stomach. I will do that for very few men and SG would be one of them. I would even confess that I thought about giving him a blow job. I'm not sure what the barriers are other than the fact that I haven't given one in so long, I need a refresher course. Heck, I didn't even know how to give a proper hand job. SG was nice enough to guide me though ("go up higher"). Next time, I will give SG my first blow job in over a year.

In between sex, SG and I cuddle, make out, and talk. He's not as open as the other boys, so I never know if he's into me or even finds me attractive. And I think that's why I'm so into him...it's the mystery of it all. Of course, as a girl, we look for every opportunity of affirmation. At one point in the night, I tell him that I think he's a little cold sometimes, and standoff-ish. He agrees and responds, "There's so many negative things about me but I can't think of one negative thing about you." OK, I will nourish my ego with that statement for the night.

At about 3am, SG has to leave so he can get some rest before his 8am meeting. We have several lingering kisses and giggles. I can't wait to see him again, and I hope it's sooner than next week.

Mr. Ireland, Date #1

I know I said I shouldn't have slept with Ireland, but he has been persistent in asking me out, so I figured "why not." Shortly after I get back to NYC from vacation, I get a text from Ireland asking when we can have dinner. Frankly, I always like to throw out the earliest possible date just so there's not much of a waiting game for either party. I respond, "tomorrow." Ireland texts back in an hour telling me he had made reservations for 6pm. Great.

After hearing stories that Ireland likes to treat his ladies right, I figure I should at least respect him by making some effort in my appearance. So I dress in black pants and a nice silk top, and curl my hair. It's the least I could do for the Irish. I show up at the restaurant in the Meatpacking District, and it's one of my favorites in NYC. Great choice. Mr. Ireland is looking nice and seems a little bit on the nervous side. We sit down and order, meanwhile catching each other up about our holidays. What I enjoy about Ireland is that he loves to laugh and he's always in a carpe diem mode. He really believes that life is too short and people should "have a laugh" whenever they can. Although I know I am not as attracted to him as I have been with the other guys, I still find him appealing and intriguing.

Throughout dinner, Ireland is very considerate towards me. He starts off dinner by saying, "This is your night, so order whatever you want and tell me whatever you need." He also consistently moves things out of my way, makes sure I get to taste everything, and even when I drop a piece of ice cream on my side of the table, he wipes it down because "I don't want your hair to accidentally fall into it." What I also like about Ireland is how much his friends care about him. For Christmas, his friend's girlfriend bought him a flat screen TV. Throughout the night, his friends and texting him to see how things are going. His roommate had already told Ireland's mom about me the night after we met. We could all use a support system like that.

After dinner, Ireland helps me put on my coat and we head to a nearby bar as he holds my hand. I still don't feel butterflies but I like being in his company. It's kind of confusing. We sit down for a few drinks and laughs. I'm wondering if he expects us to have sex tonight. We do reminisce about the night we had sex 4 times and me not remembering any of it. Ireland says he would like to refresh my memory, I get a little nervous. But, alas, he is a gentleman and tells me he has to go to his friend's bar and I have already made plans for my gay bestie at our favorite bar. As we part ways, Ireland gives me a nice hug and peck on my lips.

I am thoroughly enjoying the moment but can't help but think about my date with Sporting Goods tomorrow.

Happy New Year! Now go fuck.

Happy New Year my friends! Hope 2010 brings us all happiness, good health, and fabulous new sex partners.