Tag Archives: dating

Confessions from one of the boy’s

In the last few months I’ve been called ‘A princess’, ‘Bridget Jones’, and one of  ‘the dudes’. Apparently, my friends are just as confused about how to describe me as I am. So below is a list of confessions, that if anything, will add more to the confusion:

Confession – I have not been in a committed relationship in 7 years.

Truth be told, I’ve dated people – 1 month here, 3 months there and I’VE been committed to people. But to be in a committed relationship – both partners need to be committed. At least that’s what I’ve discovered.

Because I came out of my last relationship with as many battle wounds as one could come out with  (he was a REAL keeper – I’m pretty sure I needed the 7 years to get over everything) I began to put miles and miles of emotional distance between myself and the men I was dating/interviewing…that is, unless they weren’t really into me. If this was the case, this is when I opened up the most and would totally commit myself because well, that’s the healthy thing to do right?…No takers?

Confession – I have no filter.

Pretty much, I say everything that comes to my head. This can be a good thing…sometimes, in some ways. When it comes to me, what you see is what you get; 100% honesty, awkwardness and word vomit at all times. At a girlfriends last night she pretty much told me that I should ‘censor’ some of what I say so that, a) I don’t come off as crazy, b) I come off as attractive and c) I leave some things to the imagination.

Having no filter means that it’s very, very, very difficult for me to censor myself. I have the urge to say EVERYTHING, jokes, snippy comments, random thoughts that I trail off with. This makes it difficult when it comes to dudes because…well, I can be a lot to handle because you can’t ease into me…you get all of me, all at once. I joked back at her and said that I’m going to end up with a friend who already “loves me just as I am” – please see my Bridget Jones post.

Confession – I sing girly songs, Disney songs, and interpretive dance around my house to the songs from Glee, minimum 4 times a week.

I can’t help it. It’s so much fun to twirl around in sparkly dresses while singing Disney songs.

Confession: I have developed the ability to befriend most men.

Comments like ‘you must have a lot of guy friends’, ‘don’t worry, Jen’s one of the dudes’, &  ‘she may as well be one of the guys’ are common comments I get at work, socially (ex. at my friends 30th birthday party I sat down with her boyfriend and a bunch of guys and that was how I was introduced- glad to start out on a feminine note)  and unfortunately this is sometimes the case with guys that I’m trying to date.

How I managed this – In many ways, my sense of humour is like a boys: I watch Family Guy, Seinfeld, I’m in love with SNL – mainly Will Ferrell and I don’t get squeamish when there’s a bunch of dudes around being dudes and making inappropriate, yet REALLY funny jokes.  Actually, I often chirp in and say something even more obscene. AND I’m a little, just a little flirty. A good ego stroke is good for anyone.

Confession: I work in a male dominated office and LOVE it.

Working with men is an amazing opportunity, with minimal drama (sorry ladies), tons of jokes and a great sense of security because you have 15 big brothers.

Confession: When it comes to dating, I typically get stuck in 3 scenarios – 1) The dude wants to just be my best friend. 2) The dude just wants to bone me. 3) The dude wants to be my best friend and bone me once. What’s that all about?

I constantly get put into this ‘Friend Zone’ where all of a sudden I go from being a woman to being untouchable. I don’t want to be untouchable…I moisturize.

Also, on the exact opposite end of the spectrum, in my life I have heard of many of my male friends saying ‘I just want one chance’, ‘wouldn’t that be fun’…WTF…where’s the longevity? How did ‘one of the boys’ also become a conquest that is not worth dating. I’m not a sure thing, a onetime deal – I’m kinda funny and sometimes I can be fun.

So, even though I’m one of the boys, I’m still a woman. I own close to 50 dresses and if that doesn’t prove how much of a woman I am, I’m not sure what does.

I’m pretty sure that there are some men out there that want to see if there’s a chance between us. BUT – those are never the ones I want. Where’s the fun in having zero chase? That can be the best part – the butterflies and the stress of wondering if ‘he into you’ or if  ‘he’s just not that into you’.

And as the saying goes nice guys do finish last, it’s true…but not forever, the nice guys are the ones we marry after we’re done getting our hearts torn out, stomped on and then spit on.

Confession: I’m still single…but I’m so happy.

Because I’ve had so much time to myself, I’ve been able to cultivate the best, most supportive, large group of friends. I’m very blessed with both the wonderful, amazing and strong women in my life, but also the sweet, kind and caring men that I’ve met.

Confession: Being single for so long, it almost has become a job.

I keep myself busy 5-7 days a week – dance classes, soccer games, friend visits, dates, unnecessarily long hours at work…

Never a chance to be lonely if you’re never by yourself…except on those days when you escape from the world. Those are the best days. No answering the phone, no creeping on facebook. Just some movies and my paint brush.

So whether I’m battling through the Friend Zone, telling perverted jokes, or day dreaming of marrying Prince Harry, I’ll still word vomit all of my inner thoughts just for a laugh.


Dating = Drinking

Being the ripe ole age of 28 many of my friends are either LISING (aka. living in sin, aka. I’m joking about that term), may as well be LISING or married. So, that being said, I cannot count the times when my coupled off friends have made the comment ‘I haven’t had a drink in forever’ or ‘I haven’t been drunk in AGES’. I, myself am still single and therefore I go out on dates (some months more dates than others, but none-the-less, I am dating).

I’m not implying that I have a drinking problem or a dating problem  – I too will go AGES with out having a drink, however, when you’re dating…you’re drinking. What’s that all about? I will tell you.

Dating = Drinking – It’s a math equation:

1) First dates are awkward interviews. How many times have you been on an interview when you wished you could have a little drink to ease the stress?

2) Pretty much, until you’re ready to get down to business with someone, you want to be in a public setting – aka. Let’s meet for drinks.

3) Sad but true, having one or two drinks makes conversation easier. You’re more relaxed.

4) When it’s a bad date, a good drink can make it better.

5) Since there’s so much awkwardness around:

  • should we kiss?
  • should we not kiss?
  • should I invite him up?
  • should I not?
  • what will happen if I invite him up?
  • do I really want him to stay over?

5 – continued) Sad but true AGAIN, until you’re totally comfortable with someone, a light buzz makes all these decisions easier. It even makes a mad dash to the door a little easier – ex. ‘Oh there’s my cab, gotta go’ and then you bolt without even a high five.

So, when you are actively dating, like say a couple of dates a week, that means  you are having drinks a couple of times a week. So when you take that, and add it to your regular social life it equates to your liver wishing that you’d hurry up and find someone you like and are comfortable with because it’s sick of getting damaged, and your body’s tired of getting fat.

The Bachelor

Women everywhere seem to all have Bachelor fever.  Being a woman, I too have gotten into a couple of seasons. I really haven’t watched it since about 2004, but regardless, I can’t say that I’ve never watched it.

So, being a grown up, I realize that most people have somewhat of a past – unless they married their high school sweetheart (even then they could have a past).  However, when I am dating someone, personally I’d rather not know too much of their history. I mean some of it is necessary like ‘have you been engaged before’ ‘are you a giant cheater’. But other than that what’s the point?

Now, on The Bachelor, these women are witnessing  the Bachelor’s history happen right in front of them and they convince themselves that they are ok with it. No woman is ok with that – What’s that all about?

Here’s why I think this is BS:

1) Over night dates – What do you really think is going on when they close those hotel doors? I’ll tell you, they are touching each others privates. OR their privates, are touching each others privates. Either way, this dudes going on a date with you the next day, and you’re clearly sloppy seconds.

2) Why on earth would you ever put yourself against 24 other women? It just seems like a bad idea.

3) Public humiliation.  He has three ex-girlfriends in the period of a week and you all look like desperate crazies…Just Sayin’.

This goes for the Bachelorette as well!

The pretty one?

When I was 20 years old, my friend Meghan told me that she wanted to introduce me to a guy that she worked with at the gym (I’m going to call him Joel for the sake of this post). This was not how I typically liked to meet people at the time, but she told me he was really hot, so I thought I’d give it a try.

Earlier in the day, he popped over to mine and Meghan’s house (to size me up). He seemed very nice, very attractive (beef cake muscle-y kinda hot), but he had gold hoop earrings on. At that point in my life wearing gold in jeneral was a bad idea, it was as bad as having a silver gangsta chain on. That said, I realized I was being a total a-hole and thought I’d still give it a shot.

When we were at the bar, Joel mentioned to me that he had a kid and that his kid was the second child of a girl I had been acquainted with when I was younger.

Strike 1 – gold earrings

Strike 2 – somebodies ‘baby daddy’

Strike 3 – 2-ish kids under the age of 21…wowzers

So, because I was WAY too immature to become someones step momma, I wrote the guy off as a ‘potential’, and just had a good time with him.

At the end of the night we were at the bar, when Joel said to me:

“You know…you’re the first girl to turn me down.” What’s that all about?

You’re the first girl to turn me down? You have a baby with someone, who has two babies, you’re under 21 and you’re saying this to me? WTF!

I looked at Joel and responded:

“Joel, if we were to date you would be the pretty one. If I’m in a relationship, I want to be the pretty one.”

I know that’s a weird response, but it was the first thing that came to mind. Besides, not many girls want to date men that are prettier than them. We should take longer to get ready than they should. JS-ing.

He looked at me, smiled and said, “yeah, I can see that.”

All I can say is: WOW. Needless to say, I did not let Meg set me up with anyone after that.

Ducking solves a lot of problems

A few months back I was out with my girlfriends for a ‘Single Ladies’ night.

First we bought tons of champers (champagne) then we decorated the apartment and put out food. Second…besides my roommate, only one other person showed up – apparently everyone is tied down right now.

So, the three of us feasted, toasted and danced around the apartment.

This night also happened to be one of my best friends birthday celebrations, so because of the large turnout…I mean lack of turnout, we headed her birthday party a little earlier than we had expected. When we arrived, we were greeted with a rainbow of 5 different shots.

Our next plan was to head to a bar that was a short distant from her apartment. When we got to the bar, we headed straight to the back and placed our coats down. There’s always people that we know at this bar, so there was a lot of back and forth from the front to the back.  Because I had a second date the next day with a fellow that I barely knew, I decided that it was time for me to slow down and just socialize for a bit.

On one of my trips from the front of the bar to the back of the bar, I somehow bumped into this insanely cute guy. He was tall, friendly and extremely attractive! We chatted for a bit about the usual small talk: where are you from? what do you do? how much money do you make (JUST KIDDING –  he’s still a student)? Anyway, we were hitting it off, so when he invited me to get a drink I naturally said yes.

We were at the bar for pretty much the rest of the night and we got a little flirty – nothing out of hand…I am a lady after all. We were talking, and I think his arm was around me (or my waist) when I looked up and…


I couldn’t believe it. What’s that all about? Of all places in this giant city, how did he end up at the same place I was at, especially since we don’t really know each other and we do not run in the same circle.

Now, what does someone do in a situation like this? Well, what I did was:

I ducked.

My new friend at the bar was looking at me like a crazy person as I tried to go all ‘007’ on my date for the next day.

I then said to my new friend “I’m sorry, I don’t know what to do right now. I’m supposed to have a date tomorrow, with a guy I barely know, and he just walked in, and I’m with you, and I don’t know what to do”.

He laughed and responded – “That’s awkward”.

I then suggested that we head to the front of the bar so that I wasn’t in the direct eye line of my date for the next day.

Really, I don’t date that often.  I’m not some sort of serial dater…who does this happen to?

Needless to say, I avoided my date for the rest of the night, and continued to hangout with my new friend.

If you met him, you’d understand this decision.