J, TDR Dating Challenge

TDR Dating Challenge: Approach People (Day 9)

These dating challenges are getting TOUGH, y’all. At first it was like “yeah, I can focus on only one dating app! I can be more open! Sure!” and now I’m like “You want me to TALK TO STRANGERS?! Did you learn NOTHING about safety from your parents???” and then I realize I’m yelling at Alexa and that I am a real crazy person.

But, challenge is good! So with that, let’s move onto today’s tip.

Tip #9: Today, approach 3 strangers you find attractive and strike up a conversation with them. Try to remember what it was like to meet people before social media.

This is probably hard for a LOT of people. Introversion and social anxiety are incredibly common and very hard to overcome. Then, there’s the matter of what to SAY. Like, do I just walk up to someone and ask them to love me??? PLEASE ADVISE.

Personally, though, this should have been a breeze! I’m super extroverted, I talk to strangers all the time (at trivia, work events, parties, etc).

The REAL issue was that this challenge occurred on a Monday. I work from home on Mondays, and I watch The Bachelor on Monday nights. I don’t put on makeup. I only leave the house twice – once to go to Trader Joe’s to pick up wine, and once to go to the gym.

However, this challenge waits for NO GIRL. It was on. First stop: Trader Joe’s. I grabbed a basket and walked over to the flowers. An attractive man stood to my left. It was game time.
J – I love how beautiful these flowers are!
Man – Yeah, they’re my wife’s favorite.


I walked up to the wine tasting, hoping that would be an approachable location. As I downed sipped the taster of prosecco, I turned to the guy next to me.
J – I love this one!
Man – I really only like reds. *throws out cup and walks away*

*Looks down and realizes I am wearing what are essentially pajamas*

Trader Joe’s was obviously not doing me any favors this day. It’s fine. The gym would prove better, right? Lots of guys! Buff guys! Testosterone! Yay!

…yeah, nope. I have a fundamental aversion to hitting on people at the gym because like WE ARE TRYING TO WORK OUT HERE I DON’T WANT TO TALK TO YOU??? If you recall my gym bae saga, you’ll know how petrified I get around people who have headphones in. They are not to be bothered!

So, I failed this challenge. But, you know what?! I talk to people I don’t know every day. So, my challenge to you is to push yourself out of your comfort zone and strike up more conversations – but don’t force it where it’s not natural.

And, if a man tells you he’s married, run fast. Mama bear is never far away.


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