Tag Archive | Insecure

A Retrospective… “Box Office Hipster”

So I really didn’t have any intentions of ever writing about this guy, because he’s not a part of my life anymore and his appearance was so brief that I didn’t deem him worthy enough to grace my blog.  But I know a lot of you had mentioned you wanted some background history on my dating life and this gentleman asshole would actually be considered someone pertinent, considering he was one of the reasons why I started this blog in the first place!!

I'm not even kidding you, this is pretty much exactly how he dressed.....

I’m not even kidding you, this is pretty much exactly how he dressed…not necessarily a bad thing but yeah…

The Story….After graduating college, I was kind of at a loss as to how to meet new guys.  I knew I could always just go to the bars and try to find a guy there, but how lame is that?  Besides, there’s the stigma of finding someone at a bar, and even though some people do in fact find the love of their life at a bar, I wasn’t about to join that crowd.  Around this time, I was still seeing “Mr. Big (Present)” every once in awhile, but I was quickly losing interest since it had been so long with us doing the same thing, with no change whatsoever.  I was to the point where I was over it and I just wanted to find someone else.

Being the social butterfly that I am, I started talking to some of the guys who worked at the box office at my work (I work in the theater district…like Broadway musicals and plays…not the movie theater…).  If I remember correctly, earlier in the year, one of the guys had nervously asked for my number after I had spoken to him once.  It was really cute and he was a fairly good looking guy, so I gave him my number.  That ended up being one of the worse dates ever, with him being super nervous, awkward, and the epitome of insecure.  I mean, the guy went to the bathroom and when he came out he told me, “I’m surprised you’re still here, I thought you were going to leave while I was gone.”  Yep.  He really said that.

But enough with all that.  The guy this post is dedicated to is the friend of awkward boy I went on a date with.  I really never paid much attention to the people at the box office before, but they had renovated things so that the box office would be facing the bar that I make occasional guest appearances at and we could all stare longingly at each other if we all wanted to.  “Box Office Hipster” never really made an impression on me.  I remember having bought a ticket for something from him and him trying to talk to me but I just disregarded him.  He just never stood out and I didn’t think much of him, except he was kinda cute.  But with the renovation and being having a lot of breaks in between shows, I ended up chatting with him on occasion.  It started out pretty innocently, but eventually we began flirting…a lot!  I would even catch him staring at me from across the way on occasion, and while I was creeped out, it was kind of flattering.  But he never asked me for my number or made any indication he wanted to hang out.  So it was frustrating and intriguing all at the same time.

Finally, after two months of chatting and flirting and creepily staring, he asked for my number.  I had been working that night and so had he, so before he took off for the night, he invited me out with him and his friends.  I told him that I maybe would and that I would let him know as soon as I got off.  Well of course I went to meet up with him!!  And I ended up getting drunk.  If I remember correctly, I gave him a lap dance at the bar we were at and proceeded to make out with him a bit.  When last call hit, I knew I couldn’t drive home.  And I started to panic a bit.  I didn’t want to stay at his place since that was the first time we had ever hung out, but it was looking like I had no other option.  Outside of his friend’s place, I kept telling him I couldn’t stay at his place and I tried calling my friend who lived in the area to see if I could stay at his place (turns out I was right in front of his building as I was panicking…shows just how drunk I was).  So I ended up staying the night at “Box Office Hipster”‘s place.  He was a complete gentleman, and even offered to sleep on the floor if it would make me comfortable.

After that night, we were practically inseparable.  He would text me several times a day every single day, from the time I got up till bedtime and would want to hang out as much as humanly possible.  He even got sad/upset when he was supposed to be having a guys night and I didn’t tell him I was at a nearby bar.  Honestly, I was completely overwhelmed.  And I definitely felt smothered at times a lot of the time.  But he was good to me and he liked me, so I went with it.  He had told me I was the first girl he had been excited about in a really long time and that he really liked me.  So of course, I fell for it.   And that’s where I went wrong….



There had been several warning signs that I shouldn’t date this guy.  Right from the get go, he told me that he wasn’t good with relationships whatsoever and he usually got tired of girls after a month or so.  And from there, instead of ending it with them, he would just stop talking to them and would ignore them completely.  That should have been RED FLAG number one.  But clearly I’m an idiot.  He also didn’t have a savings account and didn’t believe in saving money; his belief was that if he earned it, he can spend it however he chose.  He had a weird thing with his image (I’m guessing it was because he was fat in high school and then lost a bunch of weight after) and literally took as long as I did, if not a tad bit longer to get ready.  And when I say get ready, I mean we would just go over to his friend’s place and he’d have to get ready to go there.  With a hat on he looked good…though I soon discovered just how awful he looked without one.  His hair was receding BADLY, and just gross looking.  He thought it was weird that I didn’t wear a lot of makeup and that I wasn’t always 100% put together all the time, because all the girls he had dated in the past wore tons of makeup, always had their hair and nails done, and always dressed up.  He also made a comment that if I lost any more weight, he couldn’t date me anymore.  Yes, he was a bit of a chubby chaser.  Closed minded doesn’t even begin to describe his thought process.  He never saw outside of the box, on anything.  He had a weird thing about being in the spotlight or the center of attention, and hated when any attention was brought onto him.  I’m the complete opposite, so you can only imagine how that went.  He thought sex or anything sexual was the reason why he lost interest in the girls in the past, so with me he didn’t want to do anything whatsoever initially.  It was like 2 weeks before we did anything but make out.  And that’s a long time for me.  Seriously…I could go on even longer than this.  But I won’t bore you all with it.

Anyways, as predicted, after about a month, he became really distant.  It was right after I had called him out for being so closed minded.  Weirdly enough, even with all the red flags going off, I was super upset that we had stopped talking.  I’m not an openly emotional person and usually do the opposite of what other girls do (i.e. girls usually text/call guys A LOT…I don’t at all; girls are always like “Oh I like you so much” and are all over the guy…I just assume the guy knows how I feel and I’m never all over him – in fact, I’m usually distant; etc.), but I started to when he stopped talking to me, telling him I missed him and shit.  What the fuck.  He also owed me some money, so I was very determined to get that back.  Not because it was a lot, just because of the principle.

Where is he now……After about a month or so of us not really speaking and him still owing me some money, he met a new girl.  She was definitely the needy, clingy, whore makeup,  Oh-my-god-I-like-you-SO-much type that he needed.  A girl who didn’t have very many friends nor a life of her own so that all her time could be spent on him.  Oh, and I should mention, she’s definitely large and in charge.  Haha.  Of course, after a month or so of casually dating, they became official and have been together ever since.  I think they even moved in together a few months after they became official.  How lovely.

Big ladies need loving too...

Big ladies need loving too…

What I learned…I realized that “Box Office Hipster” was very similar to “First” in that they both wanted me to be something that I wasn’t.  Luckily, since I had learned the first time around changing myself and who I am was not beneficial to anyone, especially myself, I didn’t change myself for this one.  But I definitely contemplated it, which scared the shit out of me.  I never thought I would do it again, and here I was contemplating it.  I think my experience with this one also further drove the point across that I should find someone who likes me for me, flaws and all, instead of someone who has an idea of what it is they want in their head and tries to make me into that.  Either way, it’s an experience that I am grateful for, and a person that I’m glad to have out of my life for good.

“Secret Sleaze”

How We Met: So this guy was supposed to be one of my 50 Dates back in 2012.  My boss “Ashlynn Peppermint” put us in contact.  He met this guy at a bar that he frequents and I guess they had become fairly good friends.  We had texted back and forth a couple of times, not ever coming up with a time that worked for both of us.  Finally, he just stopped texting me so I assumed that was that and didn’t really think twice about it.  After about a month or two of not hearing from him, I get a text out of nowhere from “Secret Sleaze” asking if I still wanted to hang out.  While I had already been hanging out with “Future Hubby”, I still wasn’t sure what we were, nor how exclusive we were.  Plus I think he was pissing me off at the time.  So I decided to go meet up with “Secret Sleaze” for a bit at a bar he was at.  He was really sweet and nice, and conversation flowed pretty well.  So we decided to set up an actual date for later in the week.


*Physical Aesthetics: 7

*Appearance: 8

*Personality: 10

*Manners: 5 & 10 (I’ll explain later)

*Intelligence: 7

*Confidence: 5-6 & 10 (again, I’ll explain)

*Overall Rating: 7

The Date: So we decided to go to the restaurant that he was supposed to take me to last year (is it just me, or is it weird to say “last year” and be referring to 2012??).  I had heard a lot of good things about this place, so I was pretty excited.  Plus he seemed like a really cool guy from just having hung out with him the one time and chatting through text, so that was nice too.

We met at the restaurant, and immediately the conversation started flowing – just like the previous time we hung out.  We talked about everything under the sun, from alcoholic drinks we like, to cars and racing them, to what we want to do with our lives.  It was really nice to go on a date with a guy who could actually keep up in conversation.  During a lot of my dates, I felt I had to try and keep conversation going and there’d be awkward moments of silence.  But not with this one!  He’s pretty funny too, so I was laughing a lot of the time.  I felt like we had a lot of good things in common, such as our love for music and our love for cars.  And the food was great too, though a bit out of the ordinary.  We ordered stuff to share and got this appetizer called “Fries with Eyes”, which was whole fried smelt with an aioli sauce.  It was really good!!  I’ve eaten a lot of weird shit, so this didn’t even phase me.  I’m not going to lie, at some points during the date I was thinking that maybe things could work out with this guy and that maybe “Future Hubby” just wasn’t the one for me at all, even though I’d already fallen for him and considered him my potential “TOWWETB”.

But there were definitely two things in our conversation that completely stuck out to me in a not so positive way.  The first would be the fact that he’s already been married and divorced.  While there isn’t anything wrong with that and I’m not one to judge a person on whether they’ve been divorced or not, I think the thing that bothered me about the fact is that it all happened at such a young age (he’s only a couple of years older than me and I’m in my twenties, so you can do the math).  He had told me he married his high school sweetheart and then a year ago they decided they weren’t really that into each other anymore.  It’s sweet to marry your high school sweetheart, but to me it’s a sign of immaturity to not only think you’re going to love your high school sweetheart forever (again, not judging people because it DOES happen and DOES work), but also to get married so soon in life.  If you truly loved a person, couldn’t you wait till you’re a bit older and maybe grow up a bit before you make a decision like that??  Marriage isn’t something to be taken so lightly.  I just feel that people who get married so young or so soon aren’t thinking realistically.  Or maybe I’m just too jaded to understand that kind of emotion.  I’m sure it’s a mix of both the former and the latter.  Plus, I’m not one to want to deal with any excess baggage; NO THANK YOU!  Anyways, on to the next subject.  The second thing that stuck out to me was his outlook on life.  I’m somewhat of a free spirit in that I don’t believe in wasting my young life away slaving away at work all the time.  Don’t get me wrong – I’ve done it in the past.  And looking back on it now, while I don’t regret it, I sometimes wish I hadn’t been working so much and had taken time for myself, to just enjoy life.  His whole outlook on life is the complete opposite of mine – his plan is to work as much as he can now and work as hard as he can so that eventually, later on in life, he’ll hopefully have a couple million in the bank and he could just live off that for the rest of his life.  Then hopefully then he’d have someone to just sit around and enjoy it with.  While I’m sure that’s the dream of a lot of people, I guess I just don’t understand it.  By the time I’m old and wrinkly, I just want to sit on my ass.  In my world, NOW is the time to be doing what you love, NOW is the time to be enjoying your life, NOW is the time to be experiencing things.  Plus, I feel when someone is so into their job that they don’t have time for anything else, they also don’t have time for dating or finding someone to date.  Or if they do have someone, they’ll never have time for that person and that person will eventually find someone who does have time for them.  So inevitably, the person who makes their job #1 above all will always be alone.  And that’s most definitely not something I want.

Okay wow, totally off topic.  Talk about a long ass rant.  Let’s digress and go back to the main point of this post….

So after dinner I offered to drive him home since he had taken a cab to the restaurant.  On the walk back to my car, it was freezing and I didn’t have a thick jacket, so he put his arm around me.  Normally, I’d consider this cute, but really it was kind of awkward.  I failed to mention earlier that “Secret Sleaze” is little…like when I wear heels, I feel like we’re the same height.  And I’m itty bitty.  So one little person attempting to hold another little person is just all too awkward.  Sorry short guys of the world, short girls don’t really like short guys either, you’re SOL.  Anyways, I drive him home and he asks me if I want to come inside and watch a movie with him.  Granted, it was only 10pm but he had to wake up at 4am so I told him I didn’t want to keep him up and I declined.  He kept trying to get me to come in, saying it was okay if I kept him up and what not.  But I put my foot down and said no.  Besides, I really just wanted to go home…I’ve been kind of a lameass homebody as of late so yeah.  Right before he left my car, he pulled my face to his and gave me a kiss.  Again, one of those moments that are supposed to be cute, but I honestly felt it was super awkward.  Because I sure as hell was not feeling that that was going to be the next move.  And it was after this that I came to the realization that he’s a bit of a sleaze.

Why you might ask…everything that had happened so far seems pretty innocent, yes?  Well…not quite.  It was until that moment when he practically insisted I come inside with him then kissed me that I put everything together.  The first night we met up was the night before New Years Eve.  Being the party girl that I am, I wanted to get a good night’s rest so that I could party it up the next night.  So I told him I was just going to hang out with him for a bit.  That night…THE VERY FIRST NIGHT WE HAD EVEN MET ONE ANOTHER, he tried to get me to stay out with him later, saying, “Oh you could just sleep over at my place.  You could even have your own side of the bed,” trying to make it sound innocent.  The on New Years Eve, I had sent him a text saying that I wasn’t going to be able to meet up with him because I was at a friend’s place and already drunk.  His response to this was, “You can come crash at my place.”  And then on our actual date, he kept asking me to come inside.   I realized after I put these 3 things together that he must have some assumption that I’m a complete whore and just go home with any guy.  Maybe…JUST MAYBE….he was trying to be friendly and just concerned about me drinking and driving or something.  But if I’m already at my friend’s house, why would you make an offer to have me come crash at your place??  Clearly they’re not going to kick me out.  And if that first night he was just trying to be nice, I feel like telling me I could sleep in his bed next to him isn’t the way to do it.  Something more along the lines of….”If you need a place to stay because you’ve been drinking, you’re always welcomed to stay at my place.”  Not, “You can sleep in my bed.  You can have your own side.”  What the fuck.  Seriously.  This goes back to the whole manners thing from above.

Again, I might be blowing everything out of proportion, but personally it didn’t seem like an innocent thing.  It pretty much sounded like this entire time he was just trying to get me to sleep with him.  And we all know I’m no hoe so it’s not just gonna happen like that!!  Hmph!

*Positives: He’s actually pretty attractive, he dresses well, he’s great conversation, he’s funny, he likes to go out and have fun, he grew up racing cars so he really knows how to drive a car

*Negatives: He’s really short, he’s already been married and divorced, he didn’t go to college (I know this makes me sound like such a bitch, but I really just can’t do guys who didn’t go to school…), he’s kind of a sleaze, I noticed that he makes fun of himself a lot and then tries to justify it right after which to me is pretty damn insecure (just own it; don’t justify it!), I feel like there have been instances where he tries too hard to be funny (which goes back to the confidence thing up above), he’s not a huge fan of sports

Second Date?: Honestly, I probably still would go on a second date with him because he was good conversation and a nice guy.  But since I have “Future Hubby”, it’s probably not going to happen.

Date #11: “Mr. Too Cool”

How We Met: This was actually a blind date/set-up by “Miss Pretty Hair” (thank you!!  =) ).  She’s been wanting me to set me up with one of her friends for awhile now and she finally did!  Apparently “Mr. Too Cool” had heard about my blog, and was willing to be one of my victims dates for it.  As of now, he is the first guy that I have gone on a date with who knows about my blog (and who I know knows about my blog…the others ones may have figured it out somehow).  “Miss Pretty Hair” gave him my number, and gave me his, but we only started talking last night.  We both had the day off so we decided to make it a day date!


*Physical Aesthetics: 6

*Appearance: 7

*Personality: 6

*Manners: 8

*Intelligence: 8-9

*Confidence: 4 & 10 (I’ll explain later)

*Overall Rating: 7

The Date: Because I love “Miss Pretty Hair” and trust her judgment 100%, I knew no matter what happened, this date could not be horrible.  She did warn me that “Mr. Too Cool” was a bit cocky; not in the sense that he tells you he’s the shit, but he has a way about him that one can tell he thinks he’s God’s gift to the Earth, so I was pretty prepped for what to expect with him.  Based on just our text messages, he seemed like a pretty cool guy.  Not too forward, not obnoxious, but just right.  We decided to meet at a restaurant right by my house.

I won’t lie, after “Miss Pretty Hair” told me about him, I looked him up on Facebook just so I could get an idea of who my date would be with.  I was happy to find out that in person he looks exactly how he did on Facebook (since this hasn’t always been my experience).  We sat at the bar and had a drink.  I ate rabbit food while he ate a sandwich…don’t judge, I’m not one of those freaks who don’t eat on dates, I just wasn’t hungry.  Haha.  Anyways, we talked about pretty much everything, from work and hobbies, to the way our minds work and living in Hippieville USA.  Conversation never stopped and it was actually pretty intellectual, which was a nice change from some of my previous dates who didn’t have brains.  After drinks, he suggested watching a movie.  Luckily, we both have an affinity for scary movies so we settled upon “The Cabin in the Woods.”  Can I just say…it is probably one of the WORST horror films I have ever seen in my life.  I wouldn’t even consider it a horror film…more so a cheesy, horror-esque film that is trying so hard to be a horror film, but can’t quite be one.  I literally thought about walking out after the first 10 minutes; it was that bad.  I’m not even sure what the point of the whole movie was.  So ya that pretty much blew ass.  Anyways, after the movie we called it a day and went our separate ways.

While the date WAS a very good date, as we all know, there has to be a downside.  Yes, I am being a Debbie Downer – deal with it.  There’s a reason I picked the nickname I did for this guy…there is just something about him that I can’t exactly pinpoint in which he appears to think he is just the best thing ever.  First off, he talked about himself nonstop.  Don’t get me wrong, I totally asked him questions about himself and I was intrigued by a lot of it.  But he talked about himself so much, that I had no idea what he was talking about at some points.  This is so ironic, because we had talked about how we both think we have ADD and we can’t do one thing for too long because we just get so bored.  Well, this one thing (him talking about himself) bored the shit out of me to the point where I zoned out.  I literally did the “nod and smile” a couple of times.  Secondly, going back to the cockiness, just the way he speaks about himself and just about things in general, you can tell that he thinks extremely highly of himself.  This is not necessarily a bad thing, but when it is depicted in someone’s speech and it is clear to an intuitive person that the person they are talking to doesn’t think their own shit stinks, it can be quite annoying.  In addition to his cocky way of speaking, he also tries to over intellectualize everything, which can be perceived as someone being very intellectual, or from my perspective, comes off as compensating for something.  This is where my rating for confidence comes in (4 & 10), because he comes off as being a very confident person who is sure of everything about himself (10), but it’s so overwhelming that it makes me think there’s a reason for this, be it insecurity or compensation for something (4).  Plus, he kept throwing in irrelevant interjections during the movie until I finally ignored him, which was annoying.

*Positives: He’s a good person to converse with, is pretty intellectual, seems pretty easy going, it was fun just hanging out with him, I didn’t feel any pressure whatsoever

*Negatives: He talks about himself FAR too much, he over intellectualizes every little thing, he reminds me too much of a friend who acts the same way with this cocky I’m-God’s-gift-to-the-world behavior and I can only take so much of my friends, so you can only imagine how I feel with “Mr. Too Cool,” his cocky behavior may be an indication of a subconscious insecurity

Second Date?: Yes, but it would have to be a long time from now.  I can’t be around people who have that “Greater than Thou” attitude about them for too long or too often, so it’d have to be in like…a month.  Or longer.