Dating Younger Men

Sunday, November 26, 2017

Precursor: This is written from a hetero/gender normative viewpoint which is my life narrative, but I do believe it is applicable to all folks.

This post has been in my notebook for some time. It’s no secret on my home team that I date younger. I’m not talking 1-2 years younger. I’m talking about 4-6 years younger….and at one point this year 7 years younger.

And when you live in a society constructed with social norms that as a woman your love life is dictated by your biological clock, which at times means ideally dating older or the same can be a little stressful.

And I will admit that today and in recent times when I’ve dated guys 5 years younger than me, I’ve often caught myself saying… “But he is SO young” “I look SO much older than him” “What if people think I’m his big sister...or his MOM”...Oh it’s bad.

Insecurities run rampant. But the truth is, I do look older, because I am older...and I am learning to be ok with that.

Because you can be a 40 year old man dating a 25 year old woman and no one bats an eye. But when you’re a woman older than 25 dating a younger man...people have all the opinions in the world.

Call it being a cougar. Call it robbing the cradle. Call it whatever you’d like. But dating younger, I’ve had much healthier relationships than dating men my own age or older. This isn’t ALWAYS the case, but this has been my personal and general experience.

So, I compiled the main reasons I’ve enjoyed dating younger the last few years:

I have a youthful energy and heart...and it is easier to make a younger guy have mature moments and conversations than it is to have an older guy set in his ways view my energy as who I am rather than not being "mature" or "serious" enough.

They respect my world doesn’t revolve around them. That I have my own life, my own friends, my own bank account, my own goals. He is part of my life, but not the center of it.

They don’t find any of the above as competition, or feel inferior or feel "less of a man"...

Younger guys brag to their friends about me, but not only in physical terms, most often it has been about, "She is so great at xyz"...and it is so refreshing to hear they're proud of me rather than intimidated.

They typically haven’t lost their soul on the corporate climb or their ethics to the dollar sign.

They also want to go stargazing with me at 1am...and yes, they also still have jobs to be at by 8am.

And they also want to stay in and drink wine and maybe later hit the bars with our friends.

Most are still less jaded about life. They offer a fresh perspective into my own life. They also make sure I am taking care of my whole self and prioritizing my needs after taking care of others. I’ve actually found me being less of a “mother figure” like people think it would be like when dating younger men...and I’ve been viewed as more of an equal partner.

And just because they're younger doesn’t mean they aren’t ready to “settle down” or not be committed or be a Dad some day….Actually most of the younger men I’ve dated want ALL of those things.

I find that many of the stereotypes of dating younger men...aren’t true, and something I’ve really learned is that age doesn’t mean much...but character does. You can be 33 or 23, but that doesn’t determine if you’re a good significant other or will treat your partner with care and love.

So...this post was probably more for me today than others, but accepting that I like, date, and some times just prefer dating younger.

Narcissist dating

Monday, October 2, 2017

...After years of working at a talent agency and then going rogue, former clients and I talk more than just about their industry. We talk about their love lives...and it has been an interesting result of the tough love conversations I've had after noticing certain themes around professional or collegiate athletes, musicians, or anything that gives you instant access to people who flock to you due to your social capital or income.

....And after my own experiences as well as watching this cycle from both ends of the spectrum in my professional and personal life, I am at the bottom of my patience bucket. Most people will say, "you write so raw" or "you're the realest"....Well, it is about to get very real.

I share this for those who are the 'fame' people and also for those of you who chase the 'famers'....Because I want to point out how vicious this cycle is. Obviously, not everyone is like this and there are plenty of exceptions.

To my 'fame' folks:

All my former clients now friends and vice versa, this was their #1 criteria in looking for a partner: All wanted a partner who was Independent.

This one made me laugh...Every 'fame' person said this...but in reality, they still did not understand why an independent partner didn't just end up at their doorstep.

Reality check.


Independent people are not waiting for you to text or call them. They are busy with what is called a LIFE. With real friends....and a real role in the world...and guess what? THEY DO NOT CARE ABOUT YOUR TOUR SCHEDULE, YOUR PHOTO SHOOT, OR YOUR GAME AT LEVI STADIUM.

Independent people already have their own thing going on. It doesn't matter if they have less money than you. Have a "smaller" status in their career if they have one at all. Independent people care the kind of person you are. You'll have to EARN their trust. They won't follow blindly.

If you lead with your status and occupation, YOU ARE LOOKING FOR FANS. For admirers. For followers, likes, and shares.


To my folks who are labeled as buckle bunnies, jersey chasers, groupies, and the ones that run after the emotionally unavailable tortured artist....

Reality check,

Stop being that person to feed their inflated popularity.

You're not doing yourself or them a favor.

They only like what you can do for them - give them their 15 minutes of extended fame. Once you have done this for them, they see little to no value in their lives.

So, if it is not a real and deep connection...cut your losses that never was a loss in the first place.

People obsessed with their own self-brand and 'fame' are constantly branding themselves, exhibit 0 empathy, and only prioritize themselves and their wants/needs over their families, friends, and humanity.

Does this sound like something you can live with forever? I would hope not.


On the real.


My almost proposal

Friday, August 25, 2017

Some people meet their sweetheart young, some are with their first love of their life.

I am not that person. 
I let a break up leave me bitter and detached. 

But a lot has happened in the last 2 years, and although I rarely think about this person now, all the cliches (Can people really change? & relationship timelines are trash!) I learned the hard way was from my relationship with this person. 


"I bought you a ring."
 Not something you wanted to hear from your ex post break up.

A few months after our break up (okay we broke up like 3, 5, who knows how many times), he let me know he had bought the ring. 

He said, it was right on time
 On time?

Our timeline of being engaged, living together in the city / me getting a job in SF, and married by the time I was 28 with a kid by the time I was 30.

I turned 28 in March, and although my life looks nothing like the life we projected, hearing he bought a ring based on a timeline (and I am sure out of guilt) made me re-think who creates these relationship timelines anyway...because they are garbage.

If a couple wants to get engaged after 3 months of dating, amazing. If a couple wants to be together and not get married, awesome. If someone wants to not do any of the above, it is no one else’s business.

So, in the last 2 years, I stopped caring about these imaginary timelines and unrealistic expectations that come with the "rules" of love.

Because does love really go by rules?

And because I am a secret rule breaker. I knew exactly what I was signing up for with this person...and I signed up anyway. I knew prior to my almost proposal that this person was not someone I'd marry, but I wanted to make things fit so badly because 1) It was on the "timeline" for my life and 2) I thought I could change him.

I thought I could make him settle down. I thought x,y,&z would make him change into exactly what I thought he should be.

Well, since that is not how love or relationships work, I learned that after several failed attempts to “make him a better person”, I FINALLY decided to listen to my home team and my gut…

So, I left. 

And after having a devastating year on top of a messy break up, I became bitter and detached. 
But at some point, I also started creating a life that I loved. One full of honesty, connection, and kept promises. I even let the bitterness turn into wisdom.

With time on my side, I also realized I loved that he was wild. I liked that he did not give one #$%@ about anyone but himself. And later I realized I needed him to give a few #$%@'s and maybe be less wild.

But that's not who he is. And that's not who I really want him to be. I would have never fallen so hard for him in the first place if we weren't so different.

So, I left; left for a life that I feel connected to, free of the societal upkeep and learning to love people for where they are and not what they could be. For loving myself for who I am, and not what I thought I should be.

Dating in San Francisco: The Ex Porn Star

Sunday, June 18, 2017

I posted about Modern Day Dating and Stranger Danger  in my last 2 dating stories, and I figured now that a year has passed, this story was safe to post.

I was sitting at this restaurant and my date was an hour late. If I wasn't hungry, I would have left because nobody disrespects my free time! Especially a first time date.

So, my date arrives all inked up, which I personally do not care, but that was not visible in his photos on Bumble. Trying to be a good date and ask questions, I asked him what this particular tattoo meant...I mean, it was a sword through a woman's face...and that was one of the less abrasive tattoos he had.

He said, "One day I dreamed about it. Drew it when I woke up, then got it tattooed...but don't worry I don't stab women in the face!"....AWKWARD LAUGH. UHHH OKAY. I am SO glad you don't stab women in the face.

So, now that we are on that page, we got into talking about past lives. He was in a metal band for years and I was exchanging road trips and tiara stories from my youth.

Then he started talking about how he used to do porn, but then he got burned out. Honestly however people want to make an income is up to them - no judgement.

Then, he started saying..."Yeah it got really weird with my Dad being the Director"...OH...OKAY. GREAT. So this was a family business!?

Again, no judgement, but this guy was an hour late, dreams of swords through women's faces, now porn is a family business, and he talked the entire time and never asked me 1 question. Not to mention he kept mentioning how he loves Asians...


So, I went to the restroom and called my friend A. I said literally drop everything you're doing and pick me up.

Inked metal ex porn star did not get a second date from me. But it sure does make for a very good story.

Welcome to dating, in San Francisco.

Dating in San Francisco: Stranger Danger

Wednesday, January 18, 2017

Dolores Park on a rare empty day.

Its been a minute since I talked about modern dating in San Francisco. And since I am not dating in 2017, I figured I'd tell you some of my most awkward and embarrassing dating stories from the year as promised.

This past June, I went to my first Pride parade in San Francisco. Hours of celebrating the significance of this gathering and little did I know I was about to watch life do its thing.

During the parade, a major tech company float had stopped in front of us and I looked at this guy and I thought, where do I know him from?...We made eye contact, started pointing to each other, and then we started mouthing, "How do I know you?!" and after exchanging an ah-ha moment while literally thousands are lined up and down the street, it's basically a rave but above ground...he pointed to his phone and told me to check mine because his float started moving forward and I wouldn't get a chance to solve this mystery.

Turns out we were snapchat friends. On snapchat, I read his name and quickly realized a couple of things...

1) Turns out parade guy actually tried getting me to hang out for 2 months...but I didn't really care because I wanted to make friends versus go on dates when I moved to San Francisco.

2) He then tried hanging out again with me 2 weeks prior to Pride (5 mos after we started talking), but I declined because I wanted to go skydiving and I didn't want to invite a new person to the group that was already going.

What is life.

We decided to do an impromptu date at Dolores Park after the parade....and I pulled every rookie move in the book!

I took a pre-made drink from a stranger, my phone was almost dead, and I didn't update my friends to tell them which park I was headed to. I thought this was going to be the next lifetime movie, but I went anyway.

To make it worse, after some very sweet compliments, you want to know what my compliments to him were?

His sock game. Hey, they were colorful.
His eye lashes. I don't think it's fair when guys have long pretty lashes.

I'm not sure it gets more awkward than this people.

Luckily, he does sales in tech and is used to schmoozing, so he was able to brush off the social awkwardness that is me and we ended up having a lot in common - I'm going to spare the details, partly because my family reads this...but turns out an impromptu date wasn't so bad after all. And overly planned, calculated me, actually had a good time....

So, stranger danger maybe wasn't so dangerous after all. 

2017: No Dating

Monday, January 16, 2017

San Francisco: Original BFF.

Being a 20 something can be confusing and eventually you learn what "advice" to take and what doesn't apply to you.

One of those subjects is dating.

With barely any dating experience up until late college, I was a late bloomer. I was definitely a chase your goals, not boys type of girl. 

Once I was done with graduate school, I started focusing on my love life.

Mainly because I fell into the illusion that many of us do after school:
Marriage is the natural next step.
As a woman, my eggs are expiring, so best get someone before I'm too old.
I am in a more stable part of life to have a consistent person.

I ended up dating....a lot, and ended up in a serious relationship, mini relationships, and handfuls of dates that all led up to this point today - single.

And I've had my fair share of funny dating stories (more to share), positive relationships, and ones that I learned a great deal from and hope to never repeat.

So, as I turn 28 this year. An age where most women have gotten married and are having kids or this is the age that we all have said, "we hope we have our first child by 28"....I'm actually claiming it as a year of no dating.

I was serious about my 2017 theme and investing into what I already have in life and from my calculations, that also means no boyfriend.

I am giving permission to re-group. Focus on my connections currently and to ignore this idea that I'm getting older so I better hurry and find someone.

I don't have this ache or feel this void like I did for so much of my 20's - feeling like I am missing out. If anything I've accepted this year that ideally I'd love to get married and have kids, but if that doesn't happen, I know I will do enough in life to make sure I am happy and fulfilled in other ways.

This isn't a pity post. There isn't anything sad about my life. Being single is a choice. Just like being married is a choice.

So, instead I also have decided to root for healthy relationships. For myself, for my friends, for my family.

Healthy, great, and immeasurably positive relationships.

I also may have picked up a new hobby where I awkwardly leave a ring emoji under my friends instagram pictures because I am hinting I want them to get engaged.

But no pressure friends - Since I won't focus on my love life, I have all the time in the world to focus on yours ;)

And on a real note, I feel good giving myself some space to not feel obligated to put myself out there when that's all I've done since the Fall of 2013.

So, cheers to a year of rooting for healthy relationships, and I am also planning to post the funny dating stories along the way from this year to relive some of my most horridly embarrassing, but very memorable moments.

Dating in San Francisco: Modern Day Dating

Tuesday, August 9, 2016

I've been meaning to write a dating post...

But it's far too embarrassing and until I get permission from former datee's or remove them from my social media, I didn't want to venture "there".

This incident though, is further removed.

My life. Some times. The things that happen. I cannot run into someone who doesn't know someone who doesn't know something horribly embarrassing about me.

So last Monday. Typical Monday. I was meeting a friend and the first few places we tried, were not working out for us.

After walking all over the city, I decided to use UBER - carpool. All of a sudden, a guy hops in the front and turns around and says my name! I was like UMMM WHO ARE YOU?!?!

Turns out, I matched with him on an online dating app and never messaged him back....Awkward. Talk about the LONGEST 3 blocks of my life riding in uber with this stranger. I was so mortified I ran out of the car and bolted across the street where I almost got ran over by a prius.

And I'm not sure about you, but when I think of my "this is how it ends"'s not by ummm, a prius.

A preview to modern dating in San Francisco.
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