Asking out a former co-worker

[Questionitall]

I am interested in asking out a former co-worker.
She was a superior that I occasionally worked with but I did not directly report to her.
I only have her email and ID on a message APP (the Line app).

Plan: Think of an action date (horse back riding for example).

A suave friend of mine advised me to ask her to meet to ostensibly talk about work.......

I think the somewhat more direct idea of doing something together is better.

Only problem is that we all know she won't be "feeling it" with an email/message.

She is a 6 and maybe 7 out of ten.....better than average but not drop dead........
Probably gets attention from guys all the time and the email/message is likely just another nuissance in her life that she does not need.

Advice?
Thanks!
I am 38 and she is 27.

 

[Black Widow Void]

Don't sabotage your intentions to her (if she doesn't resent it, she'll not respect you because you weren't direct and taking charge).

Horseback riding might not be her thing (or this would provide an excuse if she's simply not interested.) If your only option is sending a message, I'd recommend something like this:

Start off with something short and general and then....
"Once or twice, I wondered if there was more to you than just your work personality. I'm betting that there is and I'd be interested in finding out. "

 

[7onriverI f]

You might be too old for her so that's going to put her off from the start. Find girls that don't have these hangups. She might not mind with age.

 

[Glassguy]

Horseback riding for a first date? Are you going to send roses to her before the date too?

Come on man. Just invite her out for a drink.

 

[SW15]

Def don't talk about work.

I like inviting her out for a drink if you can make it work in your area with the COVID restrictions.

Activity dates can be good if you are both passionate about the same activity. You might know that about her since you were a co-worker for some time. In the absence of that knowledge, drinks are better. It is only on rare occasions that I have done the activity based first date.

 

[BackInTheGame78]

Horseback riding for a first date? Are you going to send roses to her before the date too?

Come on man. Just invite her out for a drink.

Lmao!!

 

[DEEZEDBRAH]

The past is full of low hanging fruit. If desire wasn't there, why after she was getting her **** pushed in elsewhere?

It's just lazy and says, zero options are available and your ability to source more is crap.

Actually pursue women. Not weasel your way into the past.

 

[andreihaha]

The past is full of low hanging fruit. If desire wasn't there, why after she was getting her **** pushed in elsewhere?

It's just lazy and says, zero options are available and your ability to source more is crap.

Actually pursue women. Not weasel your way into the past.

Exactly.
Also, you waited too much and you are not seen as a possible romantic partner.
I could be wrong but I doubt it.
Better to pursue others.

 

[bat soup]

Why are you being so boring and unimaginative with your dates? Horse riding? Come on, man. At least make it Ostrich or Camel Riding. Or tell her that you know a cracking Owl Sanctuary nearby that you've been dying to take her to ever since that time she looked at you and asked you why you weren't getting on with your work.

 

[andreihaha]

Why are you being so boring and unimaginative with your dates? Horse riding? Come on, man. At least make it Ostrich or Camel Riding. Or tell her that you know a cracking Owl Sanctuary nearby that you've been dying to take her to ever since that time she looked at you and asked you why you weren't getting on with your work.

That was funny.
But the inherent problem is that now they have no contact and it feels pointless, which is why he is trying to impress her by doing something unusual.
My advice, next!

 

[SW15]

The modern, white collar work environment doesn't make developing romantic relationships easy. This was even the case before #MeToo started invading the white collar space in the late 2010s.

Since at least 2000, white collar jobs have gotten absurdly difficult to obtain. The average white collar job search takes 6+ months. Recessions only make this time measurement figure lengthier. So, if a romance goes in an unpleasant direction, it's going to be very difficult to obtain a new position in a reasonable amount of time. There have been 3 mass layoff events in white collar since 2000 (9/11, Great Recession, and COVID). White collar jobs are usually the slowest to come back after a downturn. The blue collar jobs and the low wage service sector jobs come back first. Knowing that a white collar job is difficult to replace definitely puts a damper on putting the moves on a co-worker. It's not advisable to do so if you really need the job.

Likely due to the aspect of difficulty finding new jobs, #MeToo, and phobia of sexual harrassment claims, the actual white collar workspace itself has moved in a decidely non-sexual direction over the past 2 decades. The modern workspace for men involves us tiptoeing around to avoid the wrath of the HR Department, which is often staffed by women.

Because of everything I've written in the last 3 paragraphs, I think it is ok to pursue a former co-worker once someone separates from the company. There are no professional risks in that scenario. In a situation where the you as the man were laid off, then I would not recommend doing it. There's a negative power dynamic at play there. Plus, women expect a man to be employed. In a situation where you quit for a higher paying job, then you are in a better power position. If she left the company for whatever reason, it doesn't matter.

The original poster is not confident in his wording. He needs more boldness and an attitude adjustment if he is going to make the move. It also seems like this is some white collar work work environment.

Based upon how poisonous the white collar work environment has become for men, I wouldn't recommend it in a lot of cases. Men as a whole are better off doing blue collar work in the trades.

 

[bat soup]

The work issue is not a problem if you don't work there anymore and don't need her as a reference.

But I'd keep it low key - ask her out for a coffee or a drink. There's no need to offer a sports activity program out of the blue to someone who may not even remember you. It comes across as bizarre. First you should see if she's even interested in meeting you.

These elaborate activities could be good for the 2nd or 3rd time you meet and even then, it might be difficult to escalate without getting kicked in the head by a horse.

 

[evansblue]

This is a woman you don't even work with anymore, presumably don't even see anymore, and your only means of contact is an e-mail... and you're going to randomly invite her out for horseback riding? lol, what are you thinking dude?? That's something you do with a woman you've been dating 6+ months.

Why didn't you get to know her and become friends when you knew her? And don't tell me you did, because you wouldn't be left with just an e-mail if that were the case.

 

[Lookatu]

The 27yo will understand this.