Boy Diary
July 14th, 2008
Submitted by Anonymous on Mon, 07/14/2008 - 10:39.

Dear Diary,
Things with the 21-year-old from work have been heating up. We spent another night out bar hopping, this time in the gaybourhood. My new male companion is quite the pretty boy, and was drawing a lot of attention from men, who’d constantly come up to him to ask if he was gay, or there with me? We followed the evening by a nice long walk… to a parking lot. Pretty Boy drives our work’s production van, which also makes for a convenient motel on wheels. We hopped in and folded down the seats to make some room to properly maneuver. We had sex…twice…and it was steamy. Literally. We actually steamed up the entire van. We were dripping with sweat and the car smelled like liquor and sex. When we opened the doors to cool down the sun was already rising. We got dressed and jumped in the front seats. When I looked in the mirror I had rugburn on my cheek from when I been face down on the carpeted van floor getting fucked from behind. The next morning I noticed that my knees and back were also all rugburned and bruised – sex wounds are, in my opinion, badges of honour, marking a night of great sex.
A few days later, after a late night working together, Pretty Boy and I had to go back to the office for him to drop off some paperwork. It was about 10pm, and we had brought some beers to drink before meeting some other work friends at the bar. We drank and talked for a while as he finished up his work. Then he asked, “Do they have security cameras in here?”
We went into our boss’ office, and I sat down in the big black leather chair. He went up to the white board, and began to draw a picture. “Is that what you want me to do?” I asked. It was of two stick figures; the male one standing while the female was kneeling in front of him. I told him to come sit in the chair and I took of his pants. After a few minutes he stood up, lay me down on the desk, pushed up my dress and ripped off my underwear. Very hot – I know. He was fucking me so hard, pens were flying off the desk.
Suddenly the lights in the hall came on. When we walked out, the night cleaning staff was milling about. That was a close call. Definitely getting caught fucking on the boss’ desk would lead to an immediate firing, but that just made it extra naughty.
July 8th, 2008
Submitted by Little Miss X-Rated on Tue, 07/08/2008 - 14:31.

Dear Diary,
So it seems my hopes to lock up the naughty chapter of my diary and starting fresh has gone amiss. I’ve reformed to my old ways, and so I’m back to write down every juicy detail. It started when I decided I needed a crush to distract me from my ex. I’d been going to a weekly pub trivia night with friends, and directed the focus of my crushing on the adorable Quizmaster.
Each week that went by I barely said two words to him though, and worried that my flirting skills had been lost after three months of being out of practice. Finally, I turned to Facebook to make my move – the safest way to be bold, I figured. “Dear Quizmaster,” I wrote. “Should I finally work up enough nerve to say more than two words to you at the final trivia night, and actually ask you out, or would that just be an awkward situation for both of us?”
The next day I got a text message from The Gentle Giant, a guy I had dated a year ago and hadn’t seen since. After my last break-up I’d texted him for a booty call, but then quickly took back my proposal, realizing it was way too soon to jump back on the old casual sex train again. Now, weeks later, he’d invited me to see a movie with him that night, and I accepted.
Once I finished work for the day I called a coworker who I’d had my eye on, and asked him to grab dinner with me while I killed time before the movie. He’s a few years younger than me, but very pretty. After we ate I told him I had to meet a friend, but that I was going out the next night and he should join me. We hugged goodbye, and I went to meet The Giant.
It had been a year, but he looked better than ever. We did a bit of catching up in the theatre, shared a bottle of wine he’d snuck in, and we settled in for the flick. After the show, he ran into a couple he knew, and they joined us at a bar for drinks. Somehow it came up that I go to pub trivia each week. “Oh, the Quizmaster is my roommate!” The friend said. I told them how I’d just asked him out over email the night before. “I’m sure he was flattered, but I doubt his girlfriend would have liked that.” Yikes. Guys in relationships shouldn’t have their FB profile read “single”. It makes the hunt even tougher for us single gals on the prowl.
It was past my bedtime and The Giant walked me to a cab. Just before I got in he asked if I would come to his place for a bit. “I’m not going to sleep with you,” I said. He said he was fine with just making out. When I finally got in a cab an hour later, I got a text from the younger coworker asking me to come meet him for a drink. Hmmm, I hadn’t been sure if our dinner was just two friends hanging out, or a date. That text made me sure it had been the later. I declined, but said I hoped he’d come out with me the next night. And he did.
The following day after work we went to a near by bar. I ordered some nachos and several drinks. I told the hot youngin’ about a date I’d been on with Goldilocks where I’d choked on nachos and he had to give me the Heimlich maneuver. I swear to go, no more than 10 minutes later, I was choking. Unlike Goldilocks, who immediately came to my rescue, the boy just sat there and asked if I was “going to puke?” Oh, youth. Obviously I was fine, but a bit turned off by his lack of caring. His pretty eyes made me quickly overlook this.
We barhopped all night, and ended up on the patio of Jack Astor’s around last call. I decided we were both drunk enough for me to make my move. I leaned over and kissed him. Half an hour of making out later, we were kicked out of the bar. I probably should have just got in a cab, but thought the ladylike thing to do would be walk him home. We then spent the next hour making out on his front porch. This guy definitely made me feel like a kid again. He asked if I wanted to come to the side of the house with him…and off came our pants. A moment later I was leaning against a wrought iron fence as he fucked me from behind… the only thing blocking us from Wellesley was a shrub. Thankfully, most gay men walking by didn’t seem to be too concerned by alleyway sex.
I thanked the boy for a lovely evening and made my way home. I guess I’m finally ready for no-strings-attached sex again. And as for the Quizmaster, well I’m off to trivia tonight to see my little side crush. I just can’t seem to let go of my fantasy to be fucked while screaming “Oh Quizmaster…do me quizmaster!” I kid. One thing I refused to get involved in is a guy with a girlfriend. I’ve had my fair share of hurt, I don’t intend on causing any myself, despite the nice ring “Fuck me Oh Great Quizmaster” has to it.
June 24, 2008
Submitted by Little Miss X-Rated on Tue, 06/24/2008 - 10:52.

Dear Diary,
A sexy rocker once said, “It’s better to burn out than fade away”. Well, when it comes to relationships, I tend to take the opposite approach. I have a talent for dragging things out with a guy well beyond our expiration date, grasping at any hope that if we just try a little longer, we can make it work. This is until, of course, it has been dragged through the mud so long that the relationship is left totally lifeless.
This has a good side, and a bad. On the positive, I think this “fading away” is what let me still be friends with all the guys I’ve dated…and there have been a few. Once things eventually end, so far there’s been no going back, meaning that we can become just friends, with no lingering romantic feelings. Perhaps that is the test of true friendship between two people of the opposite sex – wanting to hang out, without wanting to get in their pants.
On the negative side, however, near the end of the romantic relationship, before the new ‘friendly’ one, there are usually hurt feelings and harsh words. But that’s what we do when we’re hurt… we hurt back. It’s a desperate attempt and a last resort that never solves anything. I’ve done it, and I regret it.
I started writing this diary to record all the fun (and not so much fun) from my last year of singledom. I’m now, however, looking for something more, and a diary disclosing all the juicy details of my sex life seems a bit… well, inappropriate, for the life I’m now trying to lead. Don’t get me wrong - the one night stands, getting handcuffed to chairs, falling for a certain someone, and picking up boys in bars has been fun. I just think it’s time this chapter of my diary be locked up and put back under the mattress for a while. That doesn’t mean I’ll stop writing… I just will be writing about new things.
During the time I haven’t had a boyfriend I’ve been leaving myself open to an experience I hadn’t had in quite a while – lots of girlfriends. No, I’m not going to be renaming this Girl Diary. See, I went to an all girls’ school for seven years. Seven. That much time being surrounded by cat fights, P.M.S, and “didn’t she wear that dress to last year’s semi?” left me only really wanting to stay friends with a handful of those girls, and becoming closest to my guy friends. This past year, however, I have been meeting such amazing girls, such amazing women, that I would now rather be working on building relationships with them over trolling for guys. In fact, one of these fantastic ladies, K-Star has just moved away, leaving me as heartbroken as I’d been over Mr. X. (I miss you already lady!!!)
Since I’ll be avoiding boy drama for the next little while, I’m not too sure exactly what I’ll be writing about. I guess we’ll just have to wait and see.
Wish me luck… in life, and of course, love.
xxx Little Miss X-Rated
June 2, 2008
Submitted by Anonymous on Mon, 06/02/2008 - 09:29.

Dear Diary,
I just got home from the most anticipated chick flick of the year. Of course I mean Sex And The City: The Movie. It was a week ago that things ended with Matt, formerly known as Mr. X, and this movie seemed the perfect way to start my first weekend of being single… yet again.
I loved every second of it. The movie, that is. The thought of things being done with Matt feels like a knot in my gut that is starting to loosen, but won’t go away. I also bawled my eyes out – during the movie and over him. As I walked out of the theatre I couldn’t help wondering, could Mr. X have been my Mr. Big?
Last Friday I thought it was time that Matt/Mr. X and I have another talk about where things were going with us. Well I should have listened to my horoscope that Friday, which had warned me not to bring up commitment issues. He started by saying he just wanted us to be more “real” to what the relationship truly was. The conversation ended two days later with him saying he basically just wanted to be friends. Carrie and Big go through some tough times in the movie (go figure); he just wants to be with her, but she wants to define the relationship by taking it to the next level. In the end, the lovely Carrie Bradshaw realizes that we all need to make our own rules when it comes to love, and that all relationships are different. We don’t always need to define things by traditional standards.
Matt didn’t want to be defined as a “boyfriend”, but did I push him away, and ruin a chance for us still having something special? Something that maybe didn’t need to be defined? He made me happy, so why was I complaining? What the fuck did I do, and why didn’t this movie come out before I brought up this whole “talk” thing???
Last week I thought that maybe moving on to a new guy would be my best bet at avoiding heartache. I quickly realized that was a shit idea, and cancelled my requests for random hook-ups with two gentlemen from my sexier past. I haven’t felt love in a long time, and I think I pushed Matt away because I was afraid of falling too hard, and then getting hurt. I’d been the one to end all my significant relationships in the past. I don’t know how I would have handled him maybe breaking up with me a year from now.
I keep trying to remind myself of reasons why this is probably for the best, and why we aren’t good for each other. The problem is, we hadn’t been together that long, so how could either of us really know that yet? I definitely was being a nut last week when I showed up drunk for us to discuss ending the relationship. I told him that in my “five year plan” I wanted someone I could move in with, marry, and then have a baby with. I said if he couldn’t be a boyfriend then how could he ever be that person?
Well, maybe he never would have been that person, but how can anyone know in less than three months the answer to that? Oh god, my head is spinning. This has been the longest week ever. And the horniest. I can’t help thinking of fucking Matt all day long. Riding the bus I was fantasizing about him going down on me. At my desk yesterday I couldn’t stop imagining sucking his cock. I’ve been waking up wet every morning after having sex dreams about him! I need to just take a couple of weeks where I don’t talk to him, stop over-analyzing everything, and realize that “some labels are best left in the closet”.
May 26th, 2008
Submitted by Anonymous on Mon, 05/26/2008 - 09:44.

Dear Diary,
I haven’t eaten in over a day, or left my bed in 24 hours. As you may have guessed, Mr. X and I are over.
It started a while ago, these feelings of dread, but I kind of knew what we were heading for after the finale of Grey’s Anatomy the other night. These two kids with terminal brain tumors are saying goodbye, and the guy says, “I’m not finished loving you”. After the episode I stood in the shower and cried. Matt is never going to be in love with me. At least if we end it now, I will be ok. If we wait any longer, I might be in love with him, and I just can’t handle that. Oh, Mr. X was really named Matt. I feel he’s finally deserving of a real name after two and a half months.
The next day I called him to see if we were going to do anything that weekend. He was being a bit cold and distant, same as he’d been for the past week or so. After we got off the phone I texted him saying we needed to have a “talk”. “I agree. Call you after work”, he replied. I started to cry. It was over. He called, and said he knew he couldn’t give me what I wanted, but he still wanted to be friends. “You’re doing this to me while I’m at work over the phone?!” I cried. He said he’d meet me to Yonge and Bloor at 6:00. It was 4, and Beer O’Clock at the office had just started. I needed to get drunk. I went to the kitchen and sat with some co-workers chugging back coolers. I told them what happened, and they passed me more bottles.
I met Matt in a bar and he saw that I was drunk. I told him it was good, at least I’d probably laugh now instead of cry. We talked for a couple of hours, and I continued to drink. He said he didn’t want this to be a break up, that he still wanted to hang out just as much, but that he couldn’t be a boyfriend. He just wanted us to be more realistic about what this really was. I thought I understood. We went to the Liquor Store, bought some pear cider, and sat outside on a bench to drink while I waited for K-Dubb to pick me up. “Can I kiss you one last time?” I asked. He laughed, and said it wouldn’t be that last time, but we kissed like it was. I now think it really will be. We actually hadn’t kissed, never mind even slept together, in two weeks. We would sleep in the same bed, spoon, cuddle, he’d kiss my neck or forehead, but that was all most of the time. I had brought it up before, and he said ever since his ex he’d used sex as a way to escape, but he couldn’t do that any more. That since he cared about me, having sex with me just seemed too intimate.
I know he wasn’t seeing anyone else, I believe everything he said, and he had been honest from the start about his feelings…so how could I be mad? After we parted ways I went home with my girlfriend K-Dubb to drink the rest of the cider. We went for dinner, then to The Madison. I was depressed, beginning to feel hung over, and no one looked as hot as Matt. I wanted to go home. By midnight I was sound asleep. He called Saturday morning, asking if I was ok. I said I was fine, but I’d probably call Sunday. I stayed in bed the rest of the day crying, nursing my hang over, and sleeping so I wouldn’t have to think about what would never be.
Sunday morning I wake up, and I know I need to talk again. I call, he’s asleep, but when I start to cry he says he’ll listen. “I just need to know – are you wanting me still in your life as just a friend…or as the person you’re seeing, but just without the pressure of it heading somewhere?” He basically chose friends. I cried some more, and said I still wanted him in my life, so at least now I could let go of hopes for something more. I then emailed that guy who’d written to me weeks ago with the proposition for sex, asking if the offer was still on the table. Following that I texted Goldilocks asking if I could use him for sex next week. He said that sounded good. If you fall off the bike and scrape your knee, just get on a new bike and ride again, right? Oh shit…am I just trying to get rid of this pain with meaningless sex? Oh well.
I think I’ll actually wait a couple of weeks before any new bike riding. I should make sure Matt is totally in friend mode before I sell my soul to sex (again).
May 13, 2008
Submitted by Anonymous on Tue, 05/13/2008 - 13:16.

Dear Diary,
Sorry I haven’t written in a while. I guess I’ve been pretty preoccupied with Mr. X. We’ve been dating for two months now, and we’ve had “the talk” (finally). Basically, he says that he doesn’t want to jump into anything too fast – so even though he’s basically my “boyfriend”, we’re not defining anything right now. Hmmm, that seemed to make more sense in my head than it does in writing. I get it though – he needs to sort some things out in his life before he can get too serious with me. And I’m happy with how things are right now. I still feel like there’s so much more to know about him, yet I feel a strong connection. I definitely see potential for something great with Mr. X. We’ve also said that we don’t want to see other people. Speaking of which…
Suddenly I’m basically “off the market”, and now guys from my past have started booty-calling me! This one guy, who I’d dated almost a year ago at the start of my “single life”, was at the time the best sex I’d ever had. He was so tall and big that he basically tossed me around like a rag doll. It was hot, although outside of the bedroom we barely had two words to say to each other. Anyway, two weeks ago he emails me saying he knows how I’m a fan of the forward proposition, so he’d just come out and ask if I’d like to get together for a “roll in the sack’? I replied to his message, telling him about Mr. X, and declined his hardly indecent proposal.
And remember Goldilocks? He’s been sending me drunken text messages late at night, while I’ve been in bed with Mr. X! The other day we were working on another film together and the whole time he was sending me texts from across the room with propositions of oral sex. Although Goldilocks is up there in my top 5 givers of good head, I wasn’t at all tempted.
My year of singledom and uninhibited sex seems to have done the trick in curing me of any past urges to stray. My guy’s band was playing Saturday night, and after the show as we drunkenly walked back to my place I told him about how Blondie was trying to bang me. He seemed a bit worried, but I told him that I’d rather have him spoon me for a few minutes than sleep with any other guy. In our intoxicated state it seemed like a sweeter moment than it now sounds. We walked in the door to my room, I ripped off my clothes, and we fucked until we passed out. I was happy to not have to settle for the spooning.
April 21, 2008
Submitted by Anonymous on Tue, 04/22/2008 - 08:27.

Dear Diary,
I just came back from a weekend up North with some friends. Despite the spring-like weather in the city, drive three hours north and it’s more like Ice Storm ’98. Without power, the only thing to do was drink and talk about sex - two of my favorite past times. I began to reminisce about my ex from University who had an obsession with my ass. Not in the normal “I like big butts” way, but more of an “I like the taste” kind of thing. Ya.
He would wake me up in the middle of the night with his tongue in my…well, my “other special place”, telling me he’d been dreaming about it. He was also a huge fan of anal sex. We did it a hand full of times, but frankly, the sensation of pooping backwards just wasn’t a turn-on for me. Neither was the aftermath. I’ll just leave it at that, although sitting with my friends around the fire, I went into great detail about the sounds and sights that would follow. I eventually had to make my butt off limits to him. Anal was not something I’d done before, but after dating a guy for over three years, you eventually try a lot of things.
That weekend my friends had invited Mr. X, the guy I’ve been seeing, up to the cottage too. Unfortunately he was busy, but I sure wish he’d been there to keep me warm during the night. We’ve been dating for about a month now, and I’m getting mixed advice from friends as to whether or not it’s time to have the “R.D.T.” as one called it – the Relationship Defining Talk. Are we exclusive? Is he my boyfriend? It’s been so long since I’ve had to deal with this that I don’t even remember how that came up in past relationships. Right now I’m happy with how things are, I’m just a bit nervous about a replay of what happened with the last guy I dated for over a month.
I’ll call him TV Guy (we met working on a tv show), and after about six weeks of going out to dinner all the time, sleepovers a few times a week, and him meeting my family and friends, I finally brought up if we’d stay together while he was away on vacation? “Jeez, I’ve been meaning to talk to you about that,” he says. “I’m not really looking for a girlfriend.” I think if I knew that going into things I would have been fine, but he’d been acting so “boyfriendy”, that it was a blow. Because of that guy, which was 8 months ago, I’m definitely holding back with Mr. X. If he’s also not looking for something serious, I just don’t want to get hurt again. I think I’ll give it another week before I attempt the R.D.T, and pray that he brings it up first in the mean time.
April 7, 2008
Submitted by Anonymous on Mon, 04/07/2008 - 11:18.

On the night of my 25th Birthday, almost exactly a year since my single life began, I met him… Mr. X.
My first meeting with him at The Drake had gone well, and I planned to see his band play again the following weekend. My girlfriend K-Dubb and I headed to Mod Club on the Saturday night, and after the show I went up and said hi, feeling a bit nervous. Since our meeting a few days earlier I wasn’t sure what he was thinking…he had been really sweet at The Drake, but maybe he was just being polite? The rest of the night I danced with my friends, had some drinks (ok, several drinks), and then found him again. It was close to last call, and we went to the bar to do a shot, then headed back to the dance floor. He was super sweet, dancing with me and the girls. When it was time to go home he asked if I wanted to come back with him to a friend’s house…I said sure!
We cabbed it uptown and continued our partying with a couple of his friends until the wee hours of the morning, when we headed downstairs to a bedroom. I had no intention on anything happening with him that night, and had actually not shaved b/c I was so sure nothing would... up until we started dancing I didn’t even know if he liked me or not. Anyway, I can’t give much detail to what happened next, because frankly I was so wasted that I can’t really remember. I just knew it had been good. After only a couple hours of sleep my cell phone rang. I’d forgot all about my big Birthday Brunch with the fam that was happing that afternoon. I fucked him goodbye, and found my way home.
I was feeling a little uneasy – had our romp in the sack ended any possibility for an actual relationship? My fears were put to ease when he called later that afternoon. We made plans to go on an actual date. I took him on a Tuesday night to this film screening at Camera Bar, and we had a great time. I really enjoyed just hanging out with him, and after the screening we headed to another bar. Eventually I said “I don’t mean to be presumptuous, but I’d like to come back to your place tonight.” I really wanted to have sex with him again, but this time sober. Can I just say, my god, he has a beautiful penis. Beautiful. And an amazing body. Great kisser, great sex, sweet and passionate, really amazing.
It’s now been a couple of weeks and I can’t say anything bad about him! He calls a lot, texts me, is sweet and funny. He even stayed over at my place for a couple of days. We made dinner together, went to a movie, he made me an amazing breakfast, and the sex…oh, the sex. If I thought it was good before, I can now say it’s THE BEST SEX I HAVE EVER HAD. He is amazing, truly amazing. He was going down on me and fingering me the other night and I’ve never felt anything like it…and his fucking cock. FUCK. I LOVE giving him head. I’m getting wet right now just thinking about it. (Maybe I should call him Mr. Big-Cock? Get it? Get it? Like Mr. Big…from Sex and the City? …I didn’t even come up with that my friend did. I think I’ll just stick with Mr. X for now.)
Diary, can you tell I’m happy? I’ll say cautiously happy, because he seems a bit too good to be true right now, so I’m keeping my guard up. At least I’m finally getting fucked properly.
March 27th, 2008
Submitted by Anonymous on Thu, 03/27/2008 - 11:11.

Dear Diary,
So much has happened since I last wrote…where to begin?! Well, first of all, I ended up getting a call from The Boy (the 21 year old who I’d had a one night stand with 5 months ago). He asked if I wanted to come meet up with him at a bar, and since I happened to be near by, I went. After an hour of me teasing him about how crappy he’d acted in the past, I follow him home. We didn’t have sex, but talked for hours, and then he let his fingers do the talking. (Did I actually just write that?) Well I certainly don’t learn from the past, because I basically haven’t heard from him since. That’s fine with me, because I’ve moved on to bigger and better things.
Before I get to that, though, here’s what else has happened. It was my good friend K-Dub’s Birthday a couple of weeks ago, and doesn’t Goldilocks AND one of my other ex-relationships both show up to the party. I don’t know why I’d been so into Blondie. Seeing him that night did make me feel a bit sick, but mostly because I felt freakin’ stupid that I’d been so into a guy after only two dates (who frankly wasn’t all that special).
A few days later at work I mention to a coworker that I’m “single and looking”. He tells me he has a great guy for me, and connects us over Facebook. The guy was a night editor for my old company, and seemed cute, so I figured why not when he emailed to ask me to meet. We go to a pub for some beers and pool after work, and he was very nice, but I just knew he wasn’t what I was looking for. Despite this, I end up getting drunk and making out with him practically on the pool tables. He’s emailed me a couple of times since, and I really need to tell him that nothing’s going to happen. I feel like a bitch…why am I such a kissing slut?!
A few days after that was my big quarter century party. Now this past month I’d been writing to a guy through Plenty of Fish, but hadn’t thought much about it as I’d been so wrapped up planning my party. What is kind of cute, though, is that he and I had actually messaged each other at the exact same time off the site, then things went on from there. The day before my party he tells me that his band is playing at The Drake the following Monday, so I say I’ll come. Now, back to my party…
Remember the night of the huge snowstorm? Well that was my party night. Thankfully a lot of friends still came out, and we practically had all of Revival Bar to ourselves. I had an amazing time and danced the night away. At one point I decided to take off my heels in order to strut my stuff barefoot. I then start talking to a former coworker, a 35-year-old man who’s always been a bit on the flirty side with the girls from the office. Well, he tells me he thinks my shoes are in the basement, despite my insistence that I hadn’t been down there all night. He leads me down with his hand on my ass. Next thing I know his hands are now on my chest. And then we kiss. Yikes – sooo not a good idea. I laugh it off and head back upstairs. That was kind of creepy.
Monday night I continue my Birthday celebrations by heading to The Drake to see my new online hottie’s band play. I bring K-Dubb and a bunch of other girls. When I walk into the bar he comes right up and gives me a huge hug, then says “nice to meet you”. Super cute. When he gets on stage I can’t take my eyes off him. This guy makes me drool just thinking about him. I haven’t been this attracted to anyone in a very very long time. The clock strikes midnight, and I turn the big 2-5.
The next morning I wake up to a text from him wishing me a Happy Birthday. I think this is going to be a good year.
March 14, 2008
Submitted by Anonymous on Fri, 03/14/2008 - 12:01.

Dear Diary,
Remember Goldilocks? I had really liked him, but he ended things after deciding to “give it another go” with his ex. I had to see him the other day, because there was a bit more filming to do for that movie we were working on. I ask him how things are going with the girlfriend. “We tried, we sucked, we’re finished,” he says. Interesting. A couple of friendly emails back and forth between us the following week, and I think why not, I’ll give it another try. I asked him out the first time, why can’t I again? I write Goldilocks and ask if he’d like to hang out again “friendly or otherwise”. That was a week ago, he still hasn’t written back. Boo.
What is wrong with me? Last week The Boy missed our movie date, now Goldilocks won’t respond to my email. Do they sense my desperation for a boyfriend? I was in a crappy mood Friday night and got plastered with some good friends at The Madison. It’s past last call, we’re all sitting in a booth where the piano guy sings, and I see a cute guy. Seriously, within 10 minutes, we were making out. I say bye to my friends and follow him and his incredibly wasted buddy outside. I end up getting in a cab with them and going back to his place. Correction, to his parent’s place.
We go to his room, loose some clothes, and start making out. He was covered in tattoos, which is usually so not my thing, but it was kind of hot. If I was going to do something stupid, this was the guy to do it with. I actually didn’t plan on sleeping with him. I’d even gone off my birth control a couple of weeks ago, hoping that would stop me from doing something like this. It was good, I guess, but totally not worth it. This is not the way I’m going to get my boyfriend.
Back to the drawing board. The Boy just isn’t realistically a potential b/f… he’s almost 4 years younger than me, and at this point he’s been putting off our movie date for way too long (it’s now been THREE times that he’s let me down). Goldilocks isn’t replying to my try at a reconnect, plus I recently heard some dirt on him that tells me I should just move on. The Kindergarten Teacher finally explained why he was acting distant – his ex girlfriend wants to get back together and he’s “confused”. I told him that’s something I just can’t compete with. My best bet is Mr. Nice Guy, so last night I headed to the bar he works at again to try and see him.
I went with Blossom and K. for a late dinner and drinks. Thankfully this time he was there (yippee) and he looked even cuter than I remembered. As we ate I stared longingly at him from across the bar. After we finished I suggested we take our drinks up to the counter where he was working. He’s sooo nice and we sat there for a couple of hours talking to him. Blossom thinks Mr. Nice Guy likes me, but if so then why hasn’t he asked me out? That night (a few weeks ago) that he and I danced at Grace O’Malley’s it was obvious that I am into him, so I’m not sure what’s up. At least I’m taking it slow, and up until this point I’ve resisted my urge to be aggressive and just ask him out myself. I did mention that I was heading to Gracey’s again next weekend, and that he should come, so we’ll see.
Oh, and Diary, this is kind of crazy! Remember the singer I emailed after I saw his band play last weekend? Well Blossom was at Stone’s Place Friday night and ran into him. She went up and said she’d seen him play, and that her friend (me) was “in love with” him, and had messaged him on Facebook. Get this, he says “Oh ya, Little Miss X-Rated, right?” (OK, he actually said my real name, but still…he remembered!) And then, the next day he adds me on Facebook (I’d just messaged him on it last week, not actually added him). I know it’s not really anything big, and that nothing will ever happen, but their band is playing again soon and I’m definitely grabbing Blossom and Buttercup and checking it out. My girl’s are the best wingmen ever. That’s still a while away though, but hopefully Mr. Nice Guy will come out next week. Fingers crossed.
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