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Going from Business to Pleasure, escalating in business settings

MIA_W0lf

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Rookie
Joined
Jun 26, 2019
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4
Hey fam,

Q: How can you be more aggressive, direct, or establish intent in business settings especially in the current climate?

Quick profile, I'm early 30's startup founder, down in the MIA

As a business owner (startup), I'm at networkers all the time. But more so I also host events, sit on panels, and have speaking engagements. Often, I meet amazingly beautiful women and several often walk up to me to talk business or seek advice. High percentage want to talk after and the pretense is always to provide career or business advice, be a mentor, or even be an official adviser or investor on their idea or business.

I was never the creepy douchey guy that goes after vulnerable girls or ones that just came to me for advice nor do I want to be. I have nor ever had major issues being aggressive or flirty (although consistency in escalation is a sore spot). But now there's a larger age gap, I'm too busy to find women outside of these spheres, and because of my industry (yup, I work in a space that is about women advancement, company risk mgmt, and corporate legal), it can be awkward after being on panel about advancing women in tech and then trying to ask this beautiful woman out who I've seemingly clicked with (I always mix in business talk w/ social talk and humor, I can be a charming guy ;-) ), and when I do I say something like "hey this was fun, let's keep this going and grab a coffee or drink sometime in the coming week" and her response is "yeah! let's talk business, I would love your insight on my plans". AND YES THEY ALWAYS come with a note pad or open laptop and basically start interviewing me and talking biz.

More BG:
Networkers used to be the absolute #1 place I use to pull dates especially in the West coast but often it was with peers so there wasn't a senior mentor pretense. I was in finance meeting other finance girls, or med students, lawyers, and just other women on their grind. I had no problem asking them out for clear dates. Even if there was an air of it could include shop talk, it was clear when I got the number, that this is a social thing. Im now starring across some bright-eyed 22 year old saying 'be my mentor or help be write my business plan' - - - ahh, no.

Having a mental block or road map to the transition. I'm starting to try out something simple after the first meet "Hey how about next time we meet, we do something more social, do you dance?". i don't think that'll work evey time but thinking it'll get me further than now.
 

Fuck This

Cro-Magnon Man
Cro-Magnon Man
Joined
Jul 24, 2015
Messages
2,091
That is definitely a department I'm deficient in as well. One time I had a prospect call me and she probably wanted the cover of a business meeting, but I made it personal and told her as much and she threw up some walls pronto.

if I was going to pursue someone personally I think I'd refer them to a colleague then follow up with an opener about "how's it going with so an so?"

Maybe invite them to a group thing, and talk about non-business stuff to set a personal connection. "I'm headed up to Montana to kayak....Wait you like to Kayak too? White water or lake?"

Seed an Idea about common interests outside of work. "I've always wanted to be able to go Whitewater kayaking with a girl who can keep up..."

Then follow that up with a date invite for the common interest. "Hey the Big Blackfoot is running good, wanna hit the Stretch south of town on Saturday?"
 
you miss 100% of the shots you don't take
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