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Filthy Millennial is doing everything else except that one thing...

When asking someone out, a lot of people take a direct path and when I say a "direct path," this is what I mean,

let's take a look at an example from Vulnerable Millennial,

Vulnerable Millennial: "Hey, do you want to go for a drink or coffee?"

Person of Interest: "No thanks."

Vulnerable Millennial: "Cool."

Vulnerable Millennial put themselves out there, they were rejected but, now they can continue on with their life instead of wondering if the person of interest was ever interested in them.

Therapist Brett would describe my "method" of asking someone out as follows, (This is a direct quote)

"From what you've told me; instead of just being direct with a person, you dance around them and just throw winks at them until they either respond with a wink or you eventually get over them."

Sounds about right, Therapist Brett, sounds about gawd damn right.

I ABSOLUTELY have a difficult time with rejection in my love life, I chose a career that is about 85% rejection and I just wish I could have a love life that didn't involve rejection whatsoever.

I think we can all agree that rejection blows.

Unless you're being rejected for jury duty, then it is not so bad.

The only way that I am comfortable with "trying" to hit on someone is by leaving my phone number in very creative and impressionable ways.

I'm not rejected to my face.

It's a safe and quick recovery.

I remember my first time leaving my phone number for a complete stranger,

(Now that I write it out, I probably should just stop leaving my number for complete strangers that I only see and don't talk to...who knows how many serial killers have my digits now...)

A couple of friends and I were out to dinner at a restaurant that had live jazz music nightly. It was a jazz trio but, the only solo member I was checkin' out was the bass player.

Since I was too afraid to actually go up to this guy and introduce myself, my friend told me to just send my phone number over to him.

(light bulb)

If I was going to leave my number for him, then I needed to make a great first impression.

  • My first impression has to be so good that he'll feel inclined to reach out.

  • It has to be memorable so we can tell our future children about how we met.

  • I'm going to plow through my potential first husband, future father of my future children's door with my sense of humor.

  • It has to be better than just a number on a napkin.

I began to rummage through my purse for a spare piece of paper.





I found it.

The golden ticket.

I was going to leave my phone number for him on my Victoria’s Secret Bra sizing card.

This card holds vital information, like VS bras that I have tried on, my name, and most importantly, my bra size.

From the Filthy Millennial archives, I present to you;

a photo of OG card.

*I'd like to make a note that I'm a C cup now...just so you know.*

I have never been more impressed with myself and my sense of humor until this moment.

Like wow, I'm a fuckin' hilarious catch.

Long story short, he never texted me. (LSSHNTM)

But this sparked a major trend in the dating world for me, leaving my phone number almost became an addiction.

I became addicted to being as creative as possible when leaving my phone number behind. I didn't even care if people responded, I just wanted to see what I could come up with.

For example...

*This one was about a beer that was on special, it was a pumpkin beer with a cinnamon sugar rim*

*I actually identified myself*

*My hand writing has gotten better FYI*

Long story short, he never texted me.

Another example, I had an empty candy box in my purse...

I can't remember what I wrote but, the guy who received it, got a box with my phone number inside.

Long story short, he never texted me.

For my 26th birthday, I tasked all of my friends with going around the bar and giving my phone number to any guy they deemed worthy of courting me.

How did they all drop off my phone number you may ask?

Well, I brought back a classic.

I had gone to Victoria's Secret and tried on some bras...

Just like grabbing bar coaster's for my dad from every new brewery I visit...

I grabbed a thick stack of cards and filled them all out.

I left my panty size blank because, you know, you don't want to give it all away at once.

I don't remember how many cards I had but, I received only one text and it was a selfie of two guys...

With my witty sense of humor, I responded with, "Threesome?"


With dating apps being the main source to meet anyone (especially in COVID times), I'm not able to be as creative as I would like to be when leaving an impression on someone.

It's like pulling teeth to get a guy to read your entire profile because we all know they are solely checking out your photos.

They are missing out on my hilarious bios and charming prompt answers.

For the longest time, my bio read,

"My name is Jackie and I am a motivational speaker. I eat a steady diet of government cheese and I live in a van down by the river."

So many guys thought that I was actually a motivational speaker and so many guys in Alaska asked me which river I lived near; apparently that is a normal thing in Alaska.

I cannot connect with a guy who clearly does not understand my sense of humor.

Trust me, I've tried and it is not fun.

Now that I am fully vaccinated, I feel like I want to get back out there but, at the same time...Do I want to keep throwing out more winks or just be more direct?


More winks for everyone.

Most recently, aka 2 weeks ago. I gave my phone number to a bartender. This time, I called out my plan to him.

I said, "Listen, (his name here), I'm leaving you my phone number. Do what you will with it, I don't care. I live in Chicago. Cool? Cool."


Yeah, I was probably too intimidating in that moment...

I have been brainstorming on the many unique ways that I can leave my phone number for someone while coming off as charming and less intimidating...

Please feel free to use these ideas in your own dating life.

  1. Create business cards with a list of my hobbies and a photo of me

    1. "Hey, I'm Jackie. I enjoy donuts, Wonder Woman, Cross Stitching, Running and discovering new breweries. I happen to be really funny."

  2. Literally dropping off my headshot with my "Special Skills" highlighted

    1. "Check out my many talents, here is my phone number."

  3. Going into a Male bathroom or Non Gender bathroom and writing the following,

    1. Hey, I'm Jackie. I'm a single woman who is 5'7 and I'm looking for a boyfriend. If you're into astrology and wondering if we're compatible, I'm a Cancer. This is really a woman writing this. This isn't a catfish situation. I have brown hair..well actually it looks kind of red now a days and I have hazel eyes. I have a cat named, Trigger. I have a strong sense of humor and I might come off as intimidating but please know that I don't mean to be. I'm a nice person. This is really a woman writing this. This isn't a catfish situation. I'm sitting at the bar with friends, come say "hi," and have a drink.

  4. Buying flowers from Trader Joe's and then passing them out one at a time.

    1. "Please accept this flower, as well as my phone number."

  5. Handout small packs of gum

    1. "Just in case you ate onions for dinner, here is my number."

  6. Make a "FOUND: Your Future Girlfriend poster"

    1. "Take a number and call now to setup a date!"

  7. A poster with my cat, Trigger

    1. "Are you my dad? You better call mom and let her know where you are."

  8. Sneaking my phone number into the pockets of unsuspecting men

    1. "My hand fits nicely into your back pocket, here have my number"

  9. Literally just grabbing more VS bra cards because it's a fuckin' classic move. Hasn't been successful yet but, I'm still hopeful.

  10. Literally practice being vulnerable and ask someone out to their face and if I am rejected, not take it personally.

Option 10 is probably the simplest, most direct and easiest path to take...

Therapist Brett, that son of a bitch.

He's right.

OR I can literally just wait for a guy to slip me his phone number because I have exhausted myself to the point of not even wanting to try getting a boyfriend anymore after writing this.


As crummy as dating and rejection is, the day I come across (let's be honest), I stumble into a guy who makes a comeback with a witty sense of humor, I will be flabbergasted.

He will absolutely need to continue to make the moves because I will be so stunned from laughing so hard.



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