Are You Friggin' Kidding Me?

One Bostonian's Misadventures in Dating


And finally, Lady J lands a boyfriend.

Well hello there dear readers. I’m sorry for the long absences, but I do come bearing great news! I have just recently started dating a really wonderful dude and things are going really well. Since things are legit, I don’t want to give all the details, but I will give you some of the story.

He and I met last April during the first homestand for the Red Sox. He works at the Park with me, in another department. We met through some mutual friends. Turns out we had a lot in common, so we became friends. He’s a musician (in a touring band, which is neat) who went to a certain special music school in New England. He’s absolutely hilarious and outgoing. He also loves baseball just as much as I do. His biggest downfall is pretty major though.

He’s a Yankees fan.

There’s a lot of playful banter between us, mostly because we’re silly, but also with our baseball loyalties. None of it is personal, which is good.

After spending a lot of time with him at work and hanging out with him a few times outside, I started thinking he might be into me. I wasn’t sure how I felt about it and since I didn’t want to be in any weird situations, I tried to avoid anything of the sort. I always played off that I was seeing multiple guys on the side. I never made any advances. However, I also didn’t want to be so self centered that I thought a guy was into me just because he was friendly and nice. I went back and forth with this. At one point, when I was pining over Mr. Baseball, my roommate had told me that she thought that I was going to end up with the Yankee Fan. We talked all the time, obsessively snap-chatted each other, and hung out frequently, but no moves were made.

It wasn’t until after the World Series that he and I spent more time together. I went to see his band perform and finally got to see him doing his thing. Honestly, that’s one of my favorite things to do- see people do whatever it is that they’re passionate about. Being a musician, I appreciated our long and in depth talks about music, so seeing him perform was just really great, for lack of better words. It made me see him a little differently, but at the time, I didn’t know it.

The next day was Santacon, which is my favorite pub crawl of the year. He had mentioned that he would try to meet up with me and my friends later in the day. We were texting back and forth and he finally admitted he was too tired to come out. I gave him a little crap for it and moved on. However, the following few days, I realized that I was actually really upset that he didn’t come out. I really wanted him to be with us while we partied and I was actually sad that he didn’t show up. I wasn’t sure what that meant, so I tossed the feelings aside.

Moving along, I had a Christmas party at a friend’s house the following weekend. It was in the Yankee Fan’s neighborhood, and since I had kind of wanted someone (mainly him) to come with me, I invited him. He was interested, but said he’d get back to me since he was going to see his friends perform at some club. Later, he decided that he would go with me to the party and then just duck out early for the show, which didn’t start until 11:30 or so anyway. We met up at the train that night and walked together, in a blizzard, to the party. We ended up kind of sticking to ourselves, without being completely anti social, and totally looked like a couple. In my head, I pretended that we were to see how it felt. I didn’t hate it and decided that I was open to see what would happen. He asked me if I wanted to go with him to the show downtown, and I went with him.

Long story short, we got drunk at the club with his friends and roommates and then went back to his apartment. Everyone, aside from myself, was too drunk to get home, so I navigated the taxis to the Yankees Fan’s house. His roommate (also my friend) begged me to stay over, saying I could sleep anywhere and we’d all get breakfast in the morning. What ended up happening was the roommate falling asleep on one couch, while the Yankee Fan and I fell asleep on each other on the love seat.

In the morning, he woke up and said he was going to move to his bed and said I could come with him if I wanted. I followed him and we ended up just cuddling all morning. We started getting handsy, though not pervy, and he asked me if that was me trying to say I wanted to fool around. I said no and we both stopped. However, our faces were so close that I just wanted to kiss him and see what would happen. I could tell he seemed a little rejected from not wanting to hook up, so I knew he wasn’t going to make the move. I got over my nerves and kissed him and it turned into this big magical makeout session.

Fast forward to now: We’ve hung out several times in the past month including my gym’s Christmas party, sleepover at my house, going shopping for Christmas presents for his family, seeing Frozen together, a week of long distance snap chats during the holidays, a hilarious and drunken New Years Eve (where we ended up just making out the entire night), and some hockey games at Fenway. We’ve had a few sleepovers, but no sex yet, since he’s still a little nervous about the whole thing.

However, we did have the talk and he is officially 100% my boyfriend and nothing could be better. He’s very sweet (he likes to cook me dinner) and hilarious (all we do is laugh). He’s friends with my friends and I’m friends with his. He doesn’t want to rush things. He’s too awkward to be playing me. He’s a few years younger (Cougar Status!). He’s just a really awesome guy and I’m really, very happy right now.



The Therapist

As I’ve mentioned, I’ve jumped back into the BDSM world and have been more active with my FetLife account. Fetlife, first of all, is pretty great because it’s not an actual dating site. It’s really just a sort of social media networking site for a niche group. However, if you use it to meet people, all the better.

Anyway, I have a minimalist profile. I have a few photos, none of my face, but of my mouth and a little cleavage. Nothing too revealing, just sexy enough to get attention without showing off everything. My profile says that I’m interested in learning more and finding a Daddy-Dom type personality. I get messages from some real creeps sometimes, but lately I’ve had a couple that seemed interesting.

One was from a guy that I refer to as The Therapist. His profile was minimal, like mine, but we had a nice conversation on the site. He was born and raised in Dorchester (swoon!) and still lives there. He’s working on his Ph.D. and is a Daddy-Dom. He was very nice in his messaging and not creepy at all. After a few days of chatting, we decided to meet up for a drink.

I ended up being a little late, since I opted at last minute to be a hair model for one of my friends who’s in cosmetology school. He was totally cool with it, despite my over apologizing. He was slightly embarrassed for being over dressed (he was still wearing a suit from work), but he looked fine. Very cute.

We had a great discussion about psycho analysis and how the brain works. He works at a prison as a therapist and I found it extremely fascinating, since I majored in criminology. We chatted about that, Boston sports, and he tried to analyze me. He found me difficult to figure out, saying “nothing about you makes sense”, which he seemed to like. After a chatting for awhile about “vanilla subjects”, he turned and started asking me what I was looking for and telling me what he was looking for. We talked about Dom/Sub relationships and why each of us is the way we are. It seemed like we were pretty compatable and he wanted to see me again. We left the bar, he kissed me, and we went our separate ways.

Date 2 was a few days later. I went to his neighborhood in Dorchester (have I mentioned that I love this area of Boston?) and we grabbed a drink at this Irish (duh) pub. He was a little extra flirty, putting his arm on my chair to sort of tell the other guys at the bar that I was “his”, so to speak. He suggested we go to his apartment to “watch a movie or something”. I’m not stupid, I know what this means, but sure, why the hell not?

His apartment was pretty awesome. We settled on watching Major League in his room. We cuddled and we started to make out. After getting a little handsy, I stopped to tell him that we couldn’t have sex that night. He seemed perfectly okay with that and asked me if I wanted to stop altogether. I said no, but it just couldn’t go any further. He accepted that and we went on our way to fooling around. I can see where his dominance comes out, even if I could tell he was holding back. I asked if he wanted to stop, since I was basically just a big tease for him, and he said “No, I can handle this. If it’s too much, I’ll stop, but you made yourself clear and I don’t want to push you into anything”. Alright. After awhile, he drove me home, held my hand in the car, kissed me goodnight, and off I went.

Date 3 was two days later. He came over to my apartment after work. We settled on a movie in my room, where we proceeded to fool around again. Clothes started coming off and I stopped everything to drop my H Bomb on him. He looked a little stunned, I hate having to drop that news on someone during the act, but I had a hard time figuring it into conversation before things went down, and it had to come out sooner than later. He told me he didn’t know a lot about it and that he would like to do a little research. I told him to take his time, that I wasn’t trying to pressure him. I just wanted him to know so he could make his own informed decision. He asked if we could still fool around, that he wasn’t expecting us to have sex that night anyway, and I said yes. So the night still went pretty well, even if there’s a blip on the radar now.

He told me on his way out that the week would be really busy for him, which is understandable as he works full time and is a doctorate student. I told him that I would be fine, that I had a lot of things going on, too (playoffs, baby!), so not to worry about me.

We texted the next day, but I haven’t heard from him since. I’m not taking it personally yet, but if he wants to see me, he’ll message me. I like him, but I’m not overly attached to him. He’s a great guy who is super smart and sweet. I know our sex life would be a blast. However, I don’t really understand what he wants in our relationship anyway. I don’t know if he’s looking for a girlfriend who likes kink, or if he just wants someone to fuck around with. Either one works for me, but I’m not exactly sure yet, so I don’t mind that it’s a slow process for now. And it’s totally fine if he doesn’t want to sleep with me after the bomb I dropped on him. I know I wouldn’t really want to. So I guess for now, we’ll just see how this plays out.


Mr. Baseball

Holy crap, you guys. I am suddenly and unexpectedly back in action. I’m also so excited about this, that I’m writing this way before I should. However, the way things are going, I’d have too much to write about by the time our date rolls around NEXT WEEK. Anyway, here it goes.


I got a bling from OKCupid that a guy with a high match percentage was looking at my profile last Thursday night around midnight. I was just getting ready for bed, but took a second to check it out. He had a lot in his profile that I didn’t take the time to read since I was so tired, but I saw that he was pretty cute and with a 95% match, I decided to bookmark him for the next day. I rated him 5 stars and received a message that he had rated me high as well. Even though I planned to do so the next day, I sent a quick message saying “Hi! We match pretty high, so you must be cool” basically. He messaged me back, said the same, and I told him that I only wanted to say hi quickly before I went to bed and that I would message him in the morning. He commented that he liked that I liked baseball and looked forward to chatting later.

The next morning, I read his profile and totally swooned. This guy is straight up hilarious and is even more obsessed with baseball than me. We had a lot of things in common and I was so glad I chose to look at him the night before. I wrote to him and we started chatting. After about an hour, we switched to texting.

We haven’t stopped chatting yet.

Mostly we chat about baseball and light hearted stuff. It hasn’t turned into anything inappropriate at all. It’s 100% clean and friendly, but still on the flirty side. We’re both really digging each other and are super pumped to meet up.

Downfall is that he lives about an hour away with a weird work schedule, so that makes things a little difficult for now. We do have our first date set for next Thursday. I got us free tickets to the Red Sox game (even though he HATES the Red Sox. Die hard Rays fan. He couldn’t be 100% perfect!), so we’re going to be going to that and grabbing milkshakes.

Despite his pure hatred of the Red Sox, he bought a Red Sox shirt to wear to the game. It’s of course a player shirt of a player that played for the Rays before the Sox, but the fact that he bought a Red Sox shirt for me kills me.

Soooo yea. Fingers crossed!


Every Bunny loves a good Bar Hop

So I am a HUGE fan of anything that allows me to dress in costume. It’s why I do Santacon every year. So when I discovered, through my Santacon friends, that Boston has an Easter Bunny pub crawl, I was over the moon. Last year, I couldn’t attend, but this year I made the Boston Bunny Bar Hop a priority. I invited Baby Bender to come along with my group of friends, since I know how he feels about costumes and pub crawls- the exact way I feel about them. He was just as excited as I was and met up with my roommate and me at the first stop.

Basically, we went through the whole night with bunny ears and glow sticks, hitting up the list of Bunny Approved bars in Cambridge. I had put together this really awesomely adorable/hot (go figure how that worked) outfit for my black and pink bunny costume. I got a lot of comments over my mini skirt and how my ass looked (seriously, I had never received so many compliments over my ass from so many strangers, it was a really weird feeling). I even got propositioned for a threesome with this couple. Baby Bender had a field day watching me deal with that.

So we were all pretty drunk and decided to grab Chinese food afterwards. Baby Bender and I had not been physical at all that night, aside from sitting close to each other on the couch at one bar. At the restaurant, we got a little cuddly, but nothing out of my usual nature.

Baby Bender lives downtown, whereas I live in the hipstery college neighborhoods. We were close to my house, which means far from his, so my roommate slyly asked him if he planned on staying with us. He looked at me and asked if he was and I told him he could if he wanted to.

He came home with us.

I didn’t know what his thoughts were, so I thought I’d let him do whatever he wanted really. We have an extra bed that he could have slept in, or he could stay with me of course. He followed me into my room and just stripped down and got into bed. I shrugged and changed my clothes and got into bed with him. He pulled me up to him and we just cuddled.

We stayed up talking and laughing for a few hours, when I jumped out of bed to check my bass guitar for something. When I got back into bed, he pulled me on top of him and I was a little conflicted. I knew we couldn’t have sex, thanks to my little problem, but I didn’t want to get into that whole thing with him that night. I didn’t want to tease him or lead him on, so I just kind of snuggled to him and kissed his cheek. I crawled off of him and kept cuddling with him. We started kissing, which led to a little fooling around. I told him we couldn’t have sex and he responded “Yea, that’s cool. I can still be horny and want you though, right?” I laughed and told him of course, and we just kept making out and getting all handsy. He was little shocked when he discovered my nipple piercings, because oh yea, did I tell you that my nipples were pierced? Basically that’s how that happened, haha. Anyway, nothing really escalated, and we just fell asleep afterwards.

After sleeping all day, I got up and my roommate and I decided we wanted to cook breakfast. I told him that we were going to the store and he could just stay and sleep if he wanted to. He ended up coming with us and the three of us had this cute little day of doing nothing at all at my apartment with an awesome breakfast. He ended up leaving around 4 that afternoon.

We text each other quite a bit, all innocent. Mostly about baseball, hockey, and boxing. Like I said a million times, I don’t care if nothing pans out with him. Honestly,  I don’t expect anything to. I just love being around him. He’s hilarious and a blast to be around. If all we do is get beers, watch hockey games, and make out every now and then- I’m more than okay with that.

I have this really awesome picture of the two of us from the bar hop. I wish I could post it, because it’s hilarious. Maybe one of these days.


The return of Baby Bender

Remember Baby Bender?

So every now and then we message each other, via facebook or texting. Mostly one-liners or something about Mark Wahlberg (he’s a fangirl like me). Anyway, he was going to meet up with me on St. Patrick’s Day, but never did make it out. He texted me the next day to apologize and we chatted for a little bit. I told him that I was planning on hitting up 90s night on Friday and it was in his neck of the woods if he wanted to join. Of course he was totally down and we started planning out outfits. Granted, this 90s night is super fun, but no one dresses in costumes. Both of us are costume geeks, but we played it cool for this event.

So Friday rolled around and I took my roommate and my Gym BFF (we’ll call her The Sheriff from now on, since I reference her a lot and that’s her nickname anyway) downtown. We went over to BB’s apartment which is in the heart of downtown Boston. It was the first time I’d seen him since Hurricane Sandy when he stayed at my apartment. He gave me a huge hug and took the three of us upstairs to pregame. He got along fabulously with my friends and then “yelled” at me for changing my outfit from what I told him I was going to wear. After a quick beer, we shuffled over to 90s night.

It was a lot of fun. The DJ is a friend of mine and we all had a great time. BB had a few friends meet us at the bar and they were a good time, too. He and I spent most of the night catching up and after a bit he put his arm around me. I followed suit, but didn’t read much into it.

We did chat, however, about him joining my gym. He used to box and wants to get back into it. I told him about The Boxing Instructor and how I sometimes go work out super late at night to just do regular boxing. He seems super interested and is thinking about coming in for a free trial. So yay for that!

We walked back towards his place, grabbed some pizza along the way, and he helped us hail a cab. Downtown Boston at 2am is a NIGHTMARE, so it was pretty sweet of him to stick around until we got into a car. He gave me a big hug as I left and then texted me a little bit later to make sure I got home safely.

We decided that we should hang out again soon.

Today I texted him and told him to grab some bunny ears because he would be joining me tomorrow (Good Friday) for the Boston Bunny Bar-Hop. He responded a few minutes later saying “Just picked up some ears!” so we’ll be having a fabulously good time in costume tomorrow evening.

Even if nothing ever happens between the two of us, I just love having him around. He’s just too adorable and sweet!


Brief Catch-Up on Life and Mini Marky Mark

Sorry I’ve been kind of out of it. I’ve been running around like crazy, launching a start up and everything. I also auditioned at Fenway over the weekend to be the next announcer (fingers crossed!) and got to hit in the batting cages with one of my favorite players, so things have been all weird here.


Things with Mini Marky Mark are okay, I think. I say that because I have seen him once since before New Years Eve. At first I was really panicky about it, thinking he was dodging me, but we were still in touch at least. He went to a different party on New Years, went on vacation for a few days, then had the flu, and then was at a conference for a few days. Then on top of that, he had to catch up on work. I was starting to feel like I should give up, but we were able to make plans and went out on Wednesday. Our original plans were to go to a movie, but we ended up going to our favorite hipster bar for some beers and then back to my place. I feel like I was kinda weird in the beginning, but he was very sweet during the whole night, as usual. I did tease him “Do I have to wait a whole month to see you again?”, and he laughed, said no, and then said that he had no travel plans until March for work so he’ll be around. So, I guess that’s good? I sent him a message today, seeing what his plans were for the weekend and am trying to see if we can make plans for it or if he wants to hang out next week. Hopefully things will now go more smoothly and we can actually progress here.

The one thing that set me off a little, and maybe this is just a guy thing, was how he reacted when I told him about feeling bad for one of my friends. I had mentioned that a friend of mine from the gym came to a party with me and that I was feeling bad for him because his girlfriend had dumped him via text on Christmas. MMM asked how long they were dating and I replied that I wasn’t really sure, but at least a few months. He shrugged it off and said that he should be fine and get over it and that someday he’ll grow up and learn. I didn’t really know what he meant by it and I didn’t want to dwell too much on it right then, so I just shrugged and changed the subject.

So yea- I was hoping by now we could have had the exclusivity chat and what not, but I feel like the month long absence ruined that for now. On the flip side, I honestly don’t think he’s seeing anyone else anyway- mostly because he just doesn’t have the time. I know where he works, and it’s an hour commute from his home each way. And with all the activities he does with his friends/coworkers, I can tell that he just doesn’t have time to fit in multiple women. Here’s hoping anyway. Maybe after a few more dates that are closer together we’ll be able to have the chat and be able to move the relationship along.

That’s all I’ve got for now.


The Not-Boyfriend, vol. 3

If you haven’t read the first few installments, here’s Vol. 1 and Vol 2.

So yea, in January, The Not-Boyfriend dumped me for the second time. I came home, had a good cry with my roommate, and moved on. I did not message him at all. Just moved right along.

Then comes Valentine’s Day. VALENTINE’S DAY.

He sends me a facebook message with a Some E-Card that says ‘Happy Van-Halentines Day!’ Not sure if he knew that Van Halen was my favorite band or not, but either way- I loved it. He referred to me as “Doll” which annoyed the hell out of the LomL, since he’s the only person that I know that refers to me as Doll or Dollface. He referenced my facebook status that I had up which was something to do with my awful haircut and my giant bruises from Muay Thai, saying that he hoped my bruises healed and “your hair was never horrendous”. He wasn’t currently aware of my recent venture into Muay Thai, so who knew what he was thinking my bruises were from. Anyway, I flipped out when I saw this message and thanked him and then mentioned that we should hit up another wing place sometime and invited him over for “Zombie Sunday” (my roommates and I used to get BBQ and watch The Walking Dead…barbaric and awesome). I figured we could be friends, but that was it. Wasn’t expecting him to agree at all.

He responds that he’d love to but then attached this message: “Or – I have a bottle of wine that has been sitting on my desk for over a year. (Can’t exactly show up to the frat house ready to party with a bottle of pinot, know what I mean?) If you ever wanted to come over and watch a movie and help me drink it you’re more than welcome to.”

WHAT IN THE FUCKING HELL?! It was VALENTINE’S DAY! I knew that he more than likely didn’t mean anything by it, but I didn’t want to confuse my heart any more, so I decided that I would take him up on the offer, but not on that night. We ended up getting together a few days later and I had baked some cookies before going over there to bring him. I thought that if he was offering wine, I’d offer cookies since they are my specialty and I had told him months before that I’d make him some sometime.

Well, we drank the bottle of wine and sat on the couch in his room to watch The Big Lebowski. He sat awfully close to me and I had to keep telling myself that it was nothing.

That is until he turned around to kiss me after the movie was over. So there, my heart shatters into a million little pieces all over again because I have no idea what the hell he’s doing. I let him kiss me to see if he meant to do it, but he kept coming at me. I stopped him and asked him what he was doing and if this was all okay. He said yes, but he couldn’t have sex with me. I understood that and decided, okay why not, and let the fooling around session begin.

I hung around for a little while with him afterwards and we had this really…reallllllly awkward talk. This is the talk that basically summed up everything about him that I had sorta figured out on my own.

  • He had never even kissed a girl until winter break of his senior year of college. This is also when he started drinking alcohol.
  • He didn’t lose his virginity until after the last party of senior year of college, to some frat rat.
  • He didn’t know if he was circumcised or not and flat out asked me because he knew I wouldn’t tease him (making him comfortable with me? I don’t know…).

I just wanted to hold him right then and there and take care of him. I was so confused how someone so attractive and sweet could be so “innocent”. I guess that’s the life of being a computer nerd? Man, it really blew me away, but it made everything else make sense. Of course he wouldn’t want to be with me who’s more….experienced, we’ll say. He was scared of me. Not that I’ve been around the block a million times, but yea. I scared him, plus being H-positive was just way too much for him. Understandable.

After I left that night, we started seeing each other again. I tried to keep telling myself that it was nothing and to not get too excited about it. That was hard, seeing as he actually dropped the word “relationship” once, while joking that it would be funny if we fought over a movie and that’s what ended our relationship. Every time we hung out ended with us fooling around- with no sex (intercourse, if you will).

We went on a string of dates that included our infamous Pi Day date. I became frazzled after awhile when we’d keep hanging out, but too much time would pass between dates. He went away for what I thought was only going to be a weekend conference in Florida. It ended up being over a week and then his phone was stolen…and then he went to Colorado for a week after that. I had NO idea where he was, what was up…just over all confused and slightly hurt that he wouldn’t just say “Hey I’m going out of town to visit friends for the week”. Would have saved a LOT of craziness in my brain if he would have. Or he’d tell me things he thought I’d want to hear.


Oh, and one time he gave me a pet name.

It’s all very movie-like, right? Ugh, so stupid! It drove me insane. Especially when he FORGOT my BIRTHDAY and then FORGOT to mention that he was going to EUROPE. Luckily, while all that was going on, the Love of my Life was around and pretty much made me give up on the whole thing with The Not-Boyfriend.


And then it ended when I got that really stupid message about something on facebook, that I still don’t know what he’s referring to.


So yea. That was long winded. I could be more specific, but this post would be a mile long and honestly- it’s the same thing over and over again. When he was around, he was WONDERFUL. Then 2-3 weeks would go by before we hung out again.


Yup, glad that’s over.