The Life & Times of a 54 Year Old Online Dater

Thoughts on My Experiences In Search of Love & Companionship, 10 Years Running

Do Blondes Have More Fun? February 22, 2018

Yep, it’s that time of year again.  The time of year when I consider dying my blonde hair to a different color.  I do this most every year.  It’s usually right around New Year’s that I have this fun little hair debate with myself.  Last year I actually died my hair a deep maroon color that was hella cute for about a week and then proceeded to turn every single shade of BRIGHT red imaginable.  Most of 2017 was spent trying to get back to blonde.  I am a true blonde.  No, not in the dipshitty, space cadet kinda way (sorry all you dipshitty, space cadet-y blondes).  But in the fun and bubbly, beachy kinda persona.  I just look good as a blonde.  And blonde hair looks great with a tan.

As we all know I was busy obsessing over my NYE date this year, I neglected to have my hair debate.  As I am on a self professed mini hiatus from all things online dating for the next couple of weeks, I am left with pondering hair color.  It’s sort of amazing how much mental free time I have on my hands when I’m not preoccupied with trying to over analyze every single thought, action and statement that any random man may be having regarding me (or not about me, for that matter).

This year I’m considering a lower key hair color transformation.  I was a complete toe-head as a child.  As I’ve gotten older, my natural color has gotten more dark (and grey, but I can pull those off as highlights).  I’m a dirty blonde these days (in more way than one).  I’m thinking of going brunette.  Just plain ole’ brunette.  Thoughts?


Dating Down January 29, 2018

Now, before anyone jumps my shit, take a deep breath and just read. Dating down has many connotations. Most of them negative. It implies that you’re better than someone else. That they aren’t as worthy. That they aren’t up to your standards. That is NOT what I am referring to. I don’t look down on others. Well, I do, but not my brave online dates, and if it happens, they usually deserve it for being a shitty human being.

I’m not a shitty person. As a matter of fact, I’m a damn good person. A damn good person who’s a pretty good catch. A damn good person who doesn’t need anyone else’s money. A damn good person who doesn’t care what a person has, but instead cares about who they are as person. A damn good person with some pretty significant insecurities. A damn good person who often hides these insecurities under a thick layer of self deprecation, humor and sarcasm. I’m nothing if not self aware. I know I can be an idiot a lot sometimes. I know at times that I have the emotional maturity of a petulant 7 year old. I own it though. I own it all. All my shit that is tied up in nice little compartments with decorative bows.

Dating down has nothing to do with looks or character or wealth or height or weight or anything that you can put your finger on. It has to do with me owning my shit. It has been proven time and time again that I cannot handle dating someone that I’m totally into. I turn into this crazy insecure idiot that I do not like. It brings out ALL of my insecurities and makes me question (and ultimately ruin) everything. You don’t believe me? Remember everyone’s favorite douchebag TD? The one who ruined my life (and blog) for more than 2 years more like 4years? The one that made me question absolutely everything about myself and what I brought to the table? The one who stole my happy from me and morphed from the most amazing man ever, to one of the worst? I know I had something to do with that. I always do. No one is ever blameless.

I just can’t handle really liking someone. NYE date is a prime example. I went out with the guy twice. I really liked him. If I didn’t get a text from him each morning or if he took too long to respond to a text of mine (according to my fucked up time frame), my mind would take over and I’d start spinning. It’s insane. It makes ME feel insane. It’s not a good feeling and I don’t want to do it anymore.

In the spirit of self preservation, I have decided that I can only date men that I am fairly ‘meh’ about. Guys that I like, but that I’m not 100% into. This doesn’t mean they’re not good people or unattractive, it’s just men that for whatever reason, I don’t connect with. I’m a great date with guys that I’m not all that into. I don’t second guess everything I say. I don’t worry about what they’ll think. I don’t worry if they think I’m pretty. Or if my ass looks big in these jeans. I’m just my authentic self, say what I want and let the cards fall where they may.

I have had a couple ‘meh’ dates since I moved here. I was funny and witty and charming and the guys liked me. They wanted to go out again. I agreed. Nothing has been set up yet, though. Here’s the difference: whereas I would start spinning from not hearing from a guy I like within 2 days (okay, who am I kidding, within 2 hours), I’m actually okay not hearing from them. I don’t obsess over it. My mind doesn’t create stories. My insecurities don’t come racing to the forefront. I’m okay either way hearing from them or not.

While this may sound shitty, I don’t think it is. It could be one of those things where ‘love grows’ or whatever such bullshit you read in a greeting card. I just know that for me, it’s ‘safer’ for me to not care so much. To not be so invested. To not have my mind spinning out of control. I’ve heard time and again people say that you should be with someone who loves you more than you love them. I always thought that sounded pretty sad and was a bunch of bullshit. I think that’s what I need to do though. I can’t handle it otherwise ……


Reality Check November 30, 2016

Before you all two think that my entire dating life has turned around and is going swimmingly, I feel the need to remind you that this is, of course, ONLINE dating, so there will always be those clueless people that make you scratch your head and wonder how they have survived so long.  Here’s just a couple while I work on my next actual date post! *oooh, the suspense*

Tilted Kilt: chatted a bit on Bumble.  Didn’t have much in common but what the hell, right?  He suggested we meet.  I agreed.  He suggested that we meet at Tilted Kilt.  I disagreed.  For those of you not having had the pleasure of experiencing a Tilted Kilt, it’s sort of an upscale Hooters.  Except that the uniforms are smaller.  Much smaller.  And the waitresses’ boobs are lifted to just about 2″ below their chin.  He didn’t understand why I wanted to go somewhere else, so I explained, simply, that I am not a guy.  Duh.  We never actually ended up meeting.  No great loss.

Clueless: to recap, on bumble the girl swipes left or right to signify interest.  If you swipe right on someone who has also swiped right, you are able to communicate.  So I swiped right.  He apparently swiped right.  I sent a quick (and boring) ‘Hi, you came up as a match today so I wanted to say hello’ blah, blah.  He writes back and the conversation goes something like this:

him: huh, I don’t remember ever seeing you before or swiping right

me: that’s very flattering

him: oh, sorry, I didn’t mean that

him again: but I don’t remember seeing you at all

me: nice of you to apologize, but then you said it again….

mutual: unmatch …

There have been a few other ‘interesting’ matches, but I will save those for another day.  Stay tuned for date #2 recap with 007!


Peggy or Joan is the new Ginger or Maryann……… June 1, 2015

Filed under: internet dating — Grey Goose, Dirty @ 11:40 pm
Tags: , , ,

For the record, I think I’m a combination of both Peggy AND Joan.  A mixture of all their best traits and attributes, of course. 😉

Anywhoo, I watched the finale of Mad Men several weeks ago when it aired and I LOVED IT!  And I mean LOVED, LOVED, LOVED it!

I know a Don Draper. The looks, the charm, the inner turmoil. He used to get upset with me when he would say everyone told him he looked like Colin Ferrell and I said he was more Don than Colin. I always told him he reminded me of Don Draper.  Although he physically resembles Collin Farrell more than he does Don Draper, he is, in every single aspect, Don Draper. Not John Hamm, the actor who plays him, but the character himself. He never understood that.

He is handsome and fit and perpetually searching. He has spent his life searching for happiness in other people. Being disappointed by other people. Looking everywhere but within himself to ‘fix’ things. He doesn’t think he’s good enough. He gets in his own way regarding being happy. I’m not sure he even knows how. He has flashes of contentment and peace, but I think they are few and very far between. He’s always seemingly searching for something, but instead of looking within, he looks elsewhere.

He’s got a good heart. I know he does. He doesn’t know that though. He thinks he’s bad. And unworthy. Ever since I 1st met him I’ve likened him to Don Draper. Having just watched the series finale of the show, I am convinced more than ever that I was right. He IS Don Draper.

He’ll never be happy until he finds happiness within himself. Until he stops creating drama and allows things to just ‘be’. He’s a good man, but an inherently sad one. He creates drama so that he can then turn around and feel that he is helping someone. I think it makes him feel important. Or needed. I wish he’d realize that he is important and needed just for being him. He needs to realize all that is good about himself and his life. He has so much to be thankful for.

No one can teach him this though. He always thought I was crazy when I would bring it up. He needs to figure it out for himself. The man that I always knew was an amazing person. The man that I hope someday finds his own inner peace and realizes that he is good enough.

The series finale ended with a shot of Don Draper sitting in nature (something he would never ever do), in lotus pose (another thing he would never do) and smiling. He gave away all he had. He alienated everyone who ever loved him. He gave away all of his worldly possession. It was just he, nature, yoga, morning salutations and he smiled. A genuine smile from within.  It was a pretty powerful moment.

I hope beyond hope that the Don Draper I knew someday finds this same inner peace and happiness. Although I am one of the people that once loved him and was pushed away, he deserves it. He would never admit that I was his ‘Cricket’, but he will always be Don Draper to me.