Tag Archive | Awkward


I apologize for being M.I.A. for an extremely long time.  A lot of changes have been happening in my life – some for good, some for bad.  I will write an update here soon before the end of the  month.  But until then, please enjoy a write-up on a date I went on a few weeks ago.


How We Met: We had actually “met” back in January at a shitty bar in the ‘burbs (same place I met “Humdrum”) where he was a bouncer at.  I was there for my friend’s birthday and “Stoner” kept smiling at me and checking me out.  As I was leaving, he mentioned that he really liked my straight hair.  And that was that.  A couple of weeks later, I ended up going back to this awful bar since “Indian Warrior” wanted to go out somewhere close to our houses.  That same bouncer was there and I guess he had remembered me from last time.  We talked a little bit more this time.  “Indian Warrior” noticed that he was staring and smiling at me every time I walked by, so she suggested that I keep talking to him.  At the end of the night as we were leaving, he told me that he hoped to see me again.  Being drunk and somewhat upset about how “Future Hubby” had been acting towards me, I was hoping that this guy would ask me for my number, but he didn’t.  So “Indian Warrior” (also drunk) took it upon herself to make it happen.  Such good friends I have, huh?  Anyways, she made it happen and we exchanged numbers.


*Physical Aesthetics: 7 (in a dark bar), but 5 (in a lighted area)

*Appearance: 5

*Personality: 4

*Manners: 7was

*Intelligence: 4

*Confidence: 6

*Overall Rating: 4-5

The Date: So I’m not going to lie, I was actually a bit excited for the date initially.  To the best of my memory, “Stoner” was relatively attractive and seemed fairly interested in getting to know one another.  Granted, he didn’t blow up my phone like most guys do, but I was actually okay with that.  Since we’re both so busy, it took us a bit of time to find a night to actually hang out.  I’m used to guys going after me, so it was a bit strange when he basically prompted me to contact him about the date on the day of, even though he ended up contacting me first anyways.

Earlier in the day, I told him to think of things for us to do.  I didn’t want to do the typical date stuff, because that’s just boring.  So when he called me, he suggested movies (boring), coffee (kinda boring, but better), or go-karting.  Um duh, which one do you think I picked?!  😉  So he offered to pick me up, and even walked up to my door instead of just calling me or texting me to tell me he was outside.  He also opened my door for me to get into the car.  I thought it was all super sweet.  And that’s about the only thing that I thought was sweet.

The minute we get in the car, he’s on his cell phone.  Granted, he was using GPS, but he was seriously GLUED to the thing.  I honestly don’t think he even paid attention to the first few things I said.  He was like in his own little world.  It was like that for about the first ten minutes in the car.  Finally he started talking to me and we made small talk.  I learned right off the bat that this guy was a complete joke.  First off, he definitely looked better in the dark lights of the bar I met him at.  Not attractive AT ALL in the light.  I mean, he wasn’t the ugliest thing out there, but definitely not a looker by any means.  He looked like straight up white trash (sorry if that offends anyone, I just don’t know how else to describe him).  He’s lived in various places, including Hawaii, South Dakota, Oregon, and California.  He graduated high school in South Dakota and from there went straight into construction.  I thought he was about my age, if not a little older or younger, but it turns out he’s actually 7 years older than me.  I think this really surprised me because 1.) He doesn’t look it at all and 2.) he just seemed a lot younger in both personality and maturity.  Based off just our conversations in the car, I could already tell I wasn’t going to like this guy.  Then he had to top it off with the fact that he’s a complete stoner.  Now, I don’t mind occasional drug use here and there.  It’s not personally my thing, but if it’s someone else’s, all the power to them.  But a complete stoner?  Absolutely not.  It most definitely put everything into perspective though (i.e. why he wasn’t listening to anything I was saying, why he would have delayed responses, etc.).

We finally get to the go-kart place and I’m super excited.  Then we find out it’s an hour wait.  Personally, I wouldn’t have minded waiting, but apparently he didn’t want to wait.  So we drove around trying to find something to do.  I suggested coffee so we found a Starbucks.  We got there right as they were closing so we grabbed some drinks and left.  We drove around for a bit and I was ready to just ask him to take me home, especially when I saw that he was taking me to the vicinity of his apartment.  He mentioned going to a bar around the area so I suggested we go there for a drink.  Thank god he agreed with the plan, since at this point I was already scared he was going to drug me or something.

At the bar, we order some drinks.  I had a wine, and just on a side note, it was the shittiest wine I’ve had in awhile.  So that just made my mood even worse.  Anyways, at this point we were barely talking, just saying things here and there with a lot of awkward moments of silence.  We talked a bit more here, and we have absolutely NOTHING in common.  I mean, the guy doesn’t even like sports.  I was so excited that the Nuggets game was on the t.v., and he could care less.  While I watched, he just kept playing on his phone.  I tried being nice, but my I’m-fucking-bored-and-clearly-not-interested persona started coming out.  At one point, after getting done in the restroom, he tried hugging me and kissing my cheek and I literally pushed him away, completely disgusted.  I guess this is just tangible proof that guys really don’t get hints whatsoever.  I wonder if anyone at the bar saw this awkward moment.  After this, shit got even more awkward than they already were.  He had one more drink while I just sat there sipping some water.  I really had to pee, but I was so scared he was going to slip me a roofie or something that I just held it in.  He had this really annoying stoner laugh that was just super obnoxious and I wanted to cringe every time he laughed.

Finally, after his third beer we left.  I was actually really apprehensive to have him drive me home since he mentioned he doesn’t really drink and then proceeded to drink 3 beers within less than an hour.  In the car, he apologized for making me uncomfortable by kissing me, to which I responded that it was okay (I lied).  At the intersection right before the area I live in, he most definitely ran a red arrow turning left, which scared the fuck out of me.  Luckily, there were no other cars in sight.  Either this guy was super drunk or super high…or maybe a bit of both.  When dropping me off, he got out of his car, opened my door for me, and walked me all the way to my door, stating that he was a good guy (something he had previously mentioned….).  He leaned in for a hug, but luckily not a kiss.  Phew.

I can honestly say, worst date.  Ever.

*Positives: He has some manners, he paid for everything

*Negatives: He didn’t appear to be listening to anything I had to say most of the time, he has a child and baby mama drama, he didn’t go to college, he’s not the brightest crayon in the box, he is a complete stoner (seriously got excited talking about weed), he had to mention he was a good guy on more than one occasion, is not attractive at all, we had nothing in common, nothing to really talk about.  It was all negatives, really.

Second Date?: He alluded to it on a couple of occasions, saying I was the first girl that he met at the bar that he actually went on a date with and that actually kept true to her word.  But if he texts me again, I’m most certainly telling him I’m not interested.

Date #31: “Turtle”

How We Met: We met at a mutual friend’s going away party.  Really, I should use the term “met” loosely, considering the fact that he never actually introduced himself.  In fact, I had to go ask someone what his name was after like an hour because I felt bad that he had been in the same room as me and talking to me, but I didn’t even know his name.  Basically, at this going away party, it was segregated into a lot of people upstairs and a few people downstairs.  So being the lameass that I am, I chose to hang out with the calm, quiet, few people in the basement.  And “Turtle” was one of them.  Oh and on a sidenote, this nickname isn’t a reference to Turtle on Entourage, because I’m pretty sure even he has more game than this guy I went out with.  Anyways, towards the end of the night, this guy ended up sitting right next to me, and I noticed kept scooting closer and closer to me.  I’m not a shy person, so I didn’t mind this or think twice of it.  But it was to the point where when he left his seat momentarily, this cute little dog came and practically sat on my lap, and he made the dog move so he could sit by me when he came back, gently scolding the dog for even thinking about sitting by me.  WTF.  Okay, enough with the sidenotes…so “Turtle” leaves the party without saying bye and I don’t think anything of it.  Until I find out the next day that he managed to find me on Facebook (I’ve made myself fairly private) and added me as a friend.  Not wanting to be rude, and since I met him in person, I decided to accept his friend request.  He began to message me and we set up a date to meet.


*Physical Aesthetics: 4-5

*Appearance: 6

*Personality: 3-4

*Manners: 3-4

*Intelligence: 6

*Confidence: 4

*Overall Rating: 4

The Date: I’m to the point where I’m completely over going on all these awful dates.  I know why they’re awful too.  Because I’m just not into them, nor the guys they are with.  I would rather spend my free time with people I am 100% sure I will enjoy (a.k.a my friends).  Hence why I rarely go on dates on the weekends.  Waste my lovely weekend on some guy that I know nothing will work with?  Please.

Anyways, as I’ve clearly prefaced the following, this date wasn’t good either.  We decided to meet at a bar right by my work so I could just quickly run over there afterwards.  I sent him my phone number to text me, yet he was either too timid or doesn’t text (which I highly doubt), so I didn’t even know if he was at the bar or not at our planned time.  I told him (through Facebook) that I would have to still change and what not before I met him over there so I may be later than our planned time, and all he said was, “Well I’ll see you when you’re there.”  Strange.  I could have totally stood this guy up.  So of course I take my sweet ass time getting ready and having a drink with my favorite co-workers while I’m getting ready.  It was a little over 30 minutes after I told him I would be off work, and I still hadn’t heard from him.  For a second, I thought maybe he just didn’t show.  So I was SO tempted to not even make my way over to that bar and just hang out at work, because, well…I love my co-workers.  🙂  But I didn’t want to be a total bitch, plus I still need to get to 50 guys here, so I went.  It turns out he was already there at the bar, just waiting for me.  Why he couldn’t text me to let me know he was there, especially since I showed up very late?  I do not know.

I go to sit down, and he IMMEDIATELY begins to scoot his chair extremely close to me again.  And when I say close, I mean he was practically sitting in my lap by the end of our stay at the bar.  I just thought it was so weird, and maybe that’s his way of showing he likes a girl or whatever, but it’s strange.  Anyways, we start talking and I recognize immediately that we have nothing in common.  Whatsoever.  We hang out at very different places and enjoy doing very different things.  Okay…maybe that’s a bit of an exaggeration.  But in my mind, we had nothing in common.  He works at a company that he started, working with hedge funds.  He works from home.  He goes out every once in awhile with his friends.  I did most of the talking.  Booooooring.  Luckily, my co-workers were still at work and texting me so I decided to move our date to my work, which I know is lame, but at least I would have all my favorites there to witness how awful this was all going.  As we’re closing our bill, I reach for my credit card, and “Turtle” doesn’t even blink.  He doesn’t offer to buy my drink, and just puts his credit card down and tells the bartender to split it.  Seriously??  Again, not saying I need to be paid for, but at least FUCKING OFFER!!  Be a fucking gentleman!!  I know I’m a bit of a princess in that, but I can’t help it – the guys in my life take care of me without question, so I’m just used to it.  And even when I try to buy them stuff, they refuse and make me put my money away.  True gentleman they are.  So of course I was already irritated that he didn’t offer, but I still let him come hang out with me at work.

We get to my work, and since I had been texting my co-worker “E-Slide” on how awful the date had been going already, you could tell everyone either already knew this or in their head were thinking, “What the fuck is she doing with a guy like that?!”  He just gave off a weird vibe.  Like a super timid, awkward vibe.  Anyways, we go to sit down and of course, again, he scoots his chair so close to me he’s practically in my lap.  Why he thinks this is attractive in any way, I’m not too sure.  Because I don’t like having someone I’m already uncomfortable with that close to me…ever.  But yes, he was practically in my lap again.  Luckily, my boss and “E-Slide” were in the vicinity so we all just start talking.  I kind of felt bad because at that point I kind of started ignoring him (or at least tried my best to).  He started GAWKING at me, even when I was just listening to someone else talk.  Instead of looking at the person talking, what most socially competent people would do, I would catch him just gawking at me in such a creepy way.  I seriously just wanted to die on the inside.  So can you really blame me for ignoring him?  Plus I noticed that he would change how he spoke to my boss (who’s a guy) in opposed to me or “E-Slide” – like the inflection in his voice and his demeanor changed, almost as if to “look cool” or “fit in.”  So unattractive.  He kept asking me when I was free again, and what I was going to be doing over the weekend, and luckily I’m busy so I told him that.  He seemed bummed, for what reason I don’t know, because I’m pretty sure I gave him every sign in the book that I wasn’t interested in him at all in the least bit.  When it was time to leave, “E-Slide” wanted me to walk her to her car since this one creepy security guard has been lurking around lately, so I told her I would.  “Turtle” was parked in front of the first bar we were at, which was only a block and 1/2 down the street from where we were at so I thought we were going to part ways.  But being the dumbass I can be sometimes, I offered to give him a ride to his car, which for some reason he agreed to.  Again, what the fuck.  I didn’t have a drink at work so I didn’t think to tip my boss (he was bartending), but “Turtle” definitely had two drinks, and not only did he not make any offer of payment, he didn’t even try tipping.  Horrible impression to make on someone who works in the industry.

So I walk “E-Slide” to her car, and then drive “Turtle” to his.  The entire time he’s trying to talk about my car like he knows cars so well and keeps comparing it to a hybrid.  At this point, I’m already so grossed out and not attracted to him, that I just can’t even really listen to him nor take him seriously.  We get to his car, and he gives me an awkward hug where he accidentally (but probably not accidentally, let’s be real) brushes up against my boob, then leaves.  Ugh.

*Positives: I really wish I could think of even one.  Oh…I guess he’s somewhat intellectual since he majored in biology.  And he’s from Chicago, and I’m in love with that city.  That’s about it.

*Negatives: He’s not physically attractive in any way whatsoever, he is extremely awkward, HE DIDN’T PAY FOR HIS DRINK AT MY WORK NOR TIP MY BOSS, didn’t offer to buy me a drink, weirdly kept scooting closer and closer to me, attempted to touch my leg or back every so often and it just came off as super weird and creepy, kept gawking at me for no apparent reason (also super creepy), is socially inept, has no characteristics I desire whatsoever, and clearly can’t take a hint.

Second Date?: No.  Absolutely not.  He sent me a message over Facebook (why can’t the fucker just text me?!) asking me what I was doing this weekend which I ignored.  Finally, this prompted him to text me super late at night asking me where I was at.

Date #28: “Bashful”

How We Met: We met on the (now…in my opinion) infamous dating website that I am part of, What’s Your Price.  He had “winked” at me awhile back and although after I looked at his profile I didn’t find anything of substantial interest, I did think that he seemed somewhat physically attractive.  And since I’m not really saying no to anyone (with the exception of those cheating married bastards and guys who live extremely far away from me), I figured I’d give it a shot.  It did worry me a bit that his profile said he had just gotten out of a relationship, because in my head that was a sign that he was one of those guys who needs to be in a relationship and that he was just trying to find a new person to cling on.  This notion was further corroborated in a message he sent me asking me if I was open to being in a relationship (RED FLAG, RED FLAG).  We had intended on going to dinner a couple of weeks ago but things kept getting in the way.  Finally we found a night where we were both free.  To be honest, I was a bit apprehensive to go on this date (it seems this is a constant in a lot of my dates….).  I’m getting to that point where I haven’t been as excited to go on dates and I feel like it’s more of a job than actually trying to find someone.  And I mean, the whole point of my blog was to eventually find someone.  So with that whole aspect kind of missing, I’ve been bumming.  Anyways, for the sake of my blog and the fact that I hadn’t posted a date post in awhile, I figured I’d go on the date.


*Physical Aesthetics: 8

*Appearance: 6

*Personality: 7

*Manners: 5

*Intelligence: 10

*Confidence: 6

*Overall Rating: 8

The Date: I’m not going to lie….the date went a lot better than I had expected.  And after having gone on it, I am actually very happy that I agreed to go on the date and that I met up with this guy.

“Bashful” decided to pick a restaurant that I have actually been wanting to try for awhile and haven’t gotten around to doing so, so I was actually pretty stoked to go to this restaurant.  I got there a bit early so I sat at the bar and chatted with the bartender.  Of course, like every other bar I go to, I made friends with the bartender and he made me a delicious custom drink with cognac, St. Germain, and a hint of yellow chartreuse.  It was DELICIOUS!  I never thought cognac was something I would enjoy, but the way he made the drink was delicious.

Anyways, when “Bashful” arrived, I was actually kind of awestruck.  While he looked fairly attractive in his profile picture, he was a lot better looking in person than I thought he would be.  Ya, he dressed a little frumpy, but he had just such a sweet face.  We got a table and initially, it was super awkward.  I have a feeling he doesn’t online date (granted, he DID write that he had just gotten out of a relationship on his profile) or know how to make a good first impression to begin with, because I felt like I was doing a lot of the talking.  And while I do love talking, it gets a bit awkward when I’m doing 90% of it.  So I started asking him a bunch of questions (I didn’t know what else to do…) and that most definitely got the conversation flowing.  I found out that he was an English major (as was I!!) and actually ended up getting his MA in English as well.  In addition to that, he also got his MBA in Finance.  This lead to our conversation on the fact that he used to teach English at a community college, but decided not to take that route this semester in order to further work on himself and what he really wants to do in life and to work on a business that he started with some people (in the coffee industry, roasting coffee and selling it to business).  The fact that we had our degrees in common was really exciting for me because I love finding other English majors.  We talked a lot about that…pretty much the basis of the majority of our conversation.  His main focus for English was in the psychoanalysis of literature which was really interesting to me, since mine was creative writing (hence the blog…I’ll eventually write about this in particular).  But psychoanalysis has always fascinated me in literature, so to hear someone’s take on it who truly studied it was awesome.  He started talking about how even how men and women communicate (or more so the lack of the ability to communicate properly) has everything to do with psychoanalysis.  With this he gave me the example of porn.  No joke.  But don’t worry, it’s actually a really smart analysis.  Anyways, he gave the dichotomy of there being male porn and female porn.  Male porn is completely devoid of emotion; he referred to this as “absent desire.”  It’s just straight to the point with no feelings involved whatsoever.  Where as female porn has desire, there’s usually dialogue or some sort of conversation going on besides just straight sex.  Emotion is a huge factor in female porn.  And when you think of it, even if some of us ladies like hardcore porn, he really does have a point.  It’s why we like things such as Twilight (not me, but I’m sure others do) and Fifty Shades of Grey. (Seriously, Wikipedia should love me for how many times I reference things back to their site) And it’s SO true!  He related this back to communication between men and women in that women speak from emotion, while men do not.  Obviously, this isn’t always true, but as a generalization, it most definitely is.  His knowledge about this and just how easy it was for him to turn something like porn into a completely psychoanalytical subject just blew my mind.

While we talked a lot about him, he didn’t really ask me much about myself, which I guess was okay.  Just kind of weird since in his initial message to me he said he wanted to ask me a bunch of things.  The date ended much earlier than I had expected (I had prepared myself for a long night of boring conversation and it only ended up last about 1 hour and 45 minutes), which was both good and bad.  Good in the sense that I don’t really like staying out late on weeknights, but bad in the sense that I actually really enjoyed this guy’s company and I was sad to see it come to such a quick end.  But he was tired from working all day, which is something I completely understand.  We ended the night with a hug and went our separate ways.

*Positives: He’s cute, he’s smart, he has two masters, he majored in English (like myself), he’s super busy with work and life in general, he’s a bit awkward (but in a very endearing way), he’s a total foodie

*Negatives: He’s a bit awkward, he waited for me to bring up things to talk about (but maybe he was just really shy?), he’s just as busy as me, if not even more, his manners aren’t exactly up to par (didn’t walk me to my car really, didn’t let me walk out of the restaurant first, didn’t hold the door open, etc.)

Second Date?: I really do hope so, despite some of his negative qualities, he seemed like a really cool guy that I could find myself actually liking a lot.  =)

Date #23: “Goofy”

Note: This wasn’t supposed to be a date in any way, shape, or form, but in some sense turned into one.  I seem to have a lot of these pseudo-dates, especially as of late.  Weird.

How We Met: We had a piano class together I think my junior or senior year of college.  Neither of us ever practiced, we always sat in the back, and our teacher (in my opinion) wasn’t too fond of us.  We started talking because of this.  We honestly never hung out outside of class and after graduation, we would occasionally speak on Facebook.  But that’s about it.  Keep this in mind while reading the rest…


*Physical Aesthetics: 6

*Appearance: 6

*Personality: 5-6

*Manners: 8

*Intelligence: 6 (but I couldn’t really gauge)

*Confidence: 4

*Overall Rating: 5

The Date: So like I previously stated, this was not supposed to be a date in any way.  “Goofy” had messaged me on Facebook awhile back that he was coming into town for what is called The Rocky Mountain Showdown and that we should hang out while he was in town.  I’m a friendly person so I agreed to this.  He started texting me when he got into town and it turns out he was staying at a hotel a couple blocks away from my work so I told him to come visit me at work if he got the chance.  And this is where things went sour.

He came into visit me, which was sweet, but he literally stayed at the bar the entire time.  On top of that, he was texting me the entire time I was working.  I was cocktailing that night in the back so it was obnoxious to have him text me every 5 seconds asking something.  I’m not really sure why he stayed the entire time I was working because I honestly thought he was just stopping by to say hi and then meeting up with his friends.  Anyways, we got to talking about what we were going to do that night and a co-worker and I had decided we were going to watch another one of our co-workers DJ at some bar a couple blocks away.  He said that he was meeting up with his friends, but then halfway through the night decided he was going to tag along with us (I guess I made the mistake of inviting him?).  I thought this was kind of strange because he completely changed his plans with them to hang out with me, and as I said previously, we had NEVER hung out outside of school before and I graduated college 3 years ago.  So he decides to go grab some food while I’m finishing up at work and I swear, before my shift was even over, I get a call and a message from him.  Seriously?  He knows I’m not going anywhere and that I’m meeting my co-worker at work, so I’m not sure what’s with the incessant blowing up my phone situation.  I get off of work, and he’s literally just waiting for me outside of my work.  So I make him come in while I’m getting ready.  I start complaining how my co-worker who I’m supposed to meet up with is late and I’m wondering out loud where he is, and “Goofy” makes the comment, “Sounds like you have a crush on him,” and then under his breath, “That’s a problem.”  What.  The.  Fuck.  I tell him that I don’t have a crush on him and that we’re all just supposed to hang out so I’m wondering where he is.  He starts kind of arguing with me about it, saying, “No it sounds like you like this guy” (and even if I did, why should he care?).  So I begin to explain how all of us at work are pretty close and we all love each other so damn much, so if anything it’s like a loving little family.  Not sure why I even had to explain this, but I did.

So we start heading down to this other bar because my co-worker decided we were just going to meet there instead.  On our way down, I passed by my favorite night club and of course, “Hollywood” was working.  I’ve kinda been avoiding him for some time now just because he’s been so mean to me, and in doing so, I’ve realized I don’t like him more than a friend anymore (for now…).  So because of this realization, I’m 100% okay with him as a person again.  I told “Goofy” we had to stop by (because it was on the way to the other bar) and he mentioned something about liking to find conflict.  Again, another weird comment.  I dismissed this and kept on going.  We stop by “Hollywood”‘s work and I have him do a quick, final outfit check (remember, we’re just friends now, and I’m already comfortable with him so why not).  I was dumb and wearing a red bra and a sheer white top, so I had him make sure it wasn’t obviously see through.  This apparently irritated “Goofy” enough for him to make a comment about it, so I dismissed it and told him “Hollywood” was gay.  Hahaha.

We finally arrive at our destination, and everything was fine.  He got along well with my co-worker and my co-workers friend.  We had a couple of drinks, listened to our other co-worker DJ (for like 5 seconds because we waited for forever and he didn’t start till the very end and we got impatient) and then headed out to another bar.  My co-worker and his friend decided to go to one bar  but I wanted to go to another, so I did as I pleased.  By this time, I was honestly wondering if “Goofy” had completely blown off his friends, because he kept saying they were meeting up with him but they still hadn’t shown up.  So we go and sit at the bar (really, just so I can say hi to “Boss Man” and get some water because I needed to get away from “Goofy” stat!) and just start talking.  I honestly cannot remember how we got on the topic, but he mentioned that girls in Arizona are hotter.  Which is fine, whatever.  Then I made some comment about how yeah, at the bar we were at there weren’t very many pretty girls and that (here’s where I got “cocky bitchy” as I like to call it…it happens sometimes when I’ve been drinking) I thought I was the prettiest girl there.  To this comment, he replied, “You’re hot, but you’re definitely not the hottest.”  Clearly, the fucker doesn’t know me because I was (half)kidding and I wasn’t meaning it to be arrogant, it was seriously a joke.  Anyways, my “cocky bitchy” self decided to take offense to this and I started talking about how I’ve gotten some of the hottest guys around so I don’t know what he’s talking about.  He took this as me being insecure and started telling me that I have insecurity issues.  Oh, if only the fucker knew…anyways, then shit kinda hit the fan, I called him out on being a fucking weirdo and making comments about me having a crush on my co-worker and what not.  He totally tried to back track, claiming he never said that and I was making shit up, yet I was 100% sober when he said that, and he was already drunk.  Basically, we argued about dumb shit for a good 30 minutes or so.  He kept bringing up the word “friends,” as if we were so close or something (refer back to my opening statement about this) and kept assuring me he wasn’t just trying to take me home and hook up with me for one night.  Again, What.  The.  Fuck.  Just all around.  Finally, his friend showed up, I excused myself to go to the bathroom, then got the fuck out of the bar.  He tried texting me to find me, but I just told him I went home and to have a good night.

*Positives: He’s a nice guy, complimented me all night, bought me a couple of drinks, had very good manners

*Negatives: He doesn’t seem to know the definition of what a “friend” is, he clearly has some jealousy issues, he’s clingy, we didn’t have much to talk about…like really talk about

*Second First Date?: I don’t think so.  I know he wants to hang out again before he leaves and was practically begging me to hang out pretty much the entire weekend, but after last night I’m hoping he just hates me.  It’d be better that way.

Date #21: “Kooky”

How We Met:  We met through the dating website What’s Your Price.  I hadn’t been having much luck on the website, even though my last date that I met on there, “Dream Maker” was AWESOME!!  I just hadn’t been getting a lot of “winks” (as they are called) on the website and when I did, they were men from other states.  Now, as much as I would love to fly out to another state to be paid to hang out with someone, it’s still a sketchy situation.  Anyways, “Kooky” winked at me, I gave him my offer and that was that.  We discussed when we would both be available, I suggested a place, and it was set.  Initially, like almost every other date I’ve been on, I was apprehensive to go on this one.  My apprehension with this was that he was older than me…much older.  49.  Being in my mid-twenties, that’s a bit of an age gap.  Having an affinity for younger men (yes, I rob the cradle, fucking deal with it), this territory was certainly new to me.  And while the oldest guy I had ever gone for (before this date) was 12 years older than me, this was still extremely different.  Especially considering I did not meet him in person.  Anyways, yes I was interested to see what would come of it.


*Physical Aesthetics: 8 (for his age)

*Appearance: 5

*Personality: 5

*Manners: 6

*Intelligence: 5

*Confidence: I’ll say 7 but really it’s more so N/A (I really couldn’t gauge)

*Overall Rating: 5

The Date:

Since I hadn’t gone on a date in SO long (my own doing, really), I figured I should probably go out with this guy before I went on my vacation.  I really needed to pack which is why I took the night off from work, but I got most of it done pretty early so I decided to not bail on this date.  “Kooky” left the decision up to me as to where we would meet, so I had him meet me at a bar that I had really been wanting to go to for awhile.  It’s a speakeasy style bar and I just LOVE those types of bars, so I figured what better way to experience that place than with a new person!

I got there before him, so I got us a table.  And the most awkward thing happened…sitting at the table right next to me…and when I say right next to me, I mean I could hear his conversation with the person he was with, was a guy I went to high school with and traveled to Europe with in high school.  It took me a minute to realize it was him, but when I did, it was most definitely awkward.  While it takes a lot to embarrass me (I do a good job of embarrassing myself on a regular basis so it’s almost normal to me now), this situation did in the sense that the guy I was meeting up with was not only a guy I met online, but a guy who is almost twice my age.  We both acted like we didn’t recognize each other though which was wonderful.  “Kooky” finally arrived, and (thank god…maybe not, I don’t know?) he looked just like his picture on his profile.  I’ve heard so many horror stories of people not looking the same in person as they did in their profile picture, so I feel lucky to have had similar aesthetics in both profile and in person for the two people I’ve met online.

Honestly, I’ve had some really bad dates (as I’m sure you can/have read in my past posts), but this one was pretty bad.  He was a nice guy, but we had NOTHING to talk about.  There were moments where there was an awkward lull in conversation, and I literally had to think of anything I could to initiate conversation once more.  I felt that it was me doing most of the talking and him kind of just answering.  He works as the manager of a facility which deals with senior citizens with mental disabilities.  His company helps aid these disabled citizens in finding homes, jobs, etc.  This is most definitely an admirable job, but I felt that he himself could perhaps use the help he is giving to these people.  The way he spoke to me and just spoke in general was very strange…I’d say eccentric, but it was beyond that.  It was almost as if he had a mental deficiency himself.  But he did graduate from Dartmouth so I’m not too sure what to think of that either.  The conversation was very forced the entire time and we had NOTHING in common.  Basically, if I liked something, he hated it.  We talked a lot about alcohol and drinking (I’m a bartender, that shit always comes up), and he pretty much hates every alcohol I like.  I love vodka and whiskey, he likes gin.  Seriously??  Nothing in common.  I hate to blame the age gap, but I’m going to go with the probability that a lot of it has to do with him being almost twice my age.

We finally found common ground on the next bar that we went to (which ironically is the same bar/restaurant that I went to with “Almost Birthday Twin”) when we started talking sports.  While we still weren’t into the same sports (he loves football and nothing else really, I love basketball), the conversation flowed much better when talking about this.  At one point I had to pee, so I left my drink at the bar (duh).  Honestly, I was terrified he was going to roofie me (yes I can be a bit of a hypochondriac), so I set my beer up in such a way that I would know if it was touched when I got back.  And I really did think my beer moved and that he had roofied me when I got back.  But I never blacked out so I guess not?  Haha.  Anyways, the night ended about 2 1/2 hours after it started, with a nice little bonus at the end ($$$).

*Positives: He was a nice guy, he looked like what he did in his profile picture, he paid for everything (but I’m not sure if that’s a positive considering the website says they have to)

*Negatives: We have absolutely nothing in common, he’s weird as fuck, he’s old, I think he may have his own mental disability…honestly I could go on and on and on…

*Second Date?: Ya, I don’t think so.