My boss at my new job is pretty hot, is it possible for a younger man to seduce an older woman?

devilkingx2

Master Don Juan
Joined
Jul 9, 2013
Messages
4,546
Reaction score
2,243
Location
NYC
Alright guys let me update y'all.

Thursday night was office night, it's a weekly thing where the branch owner takes everyone out. This week we went to a bar and I got to meet most of my coworkers. Several attractive women, cool bros who will make good friends, etc. Everybody is nice and friendly and there's some friends I can make. But I don't think any of the girls will give me the time of day in terms of dating (yet)

Friday morning the branch owner had the morning meeting at IHOP so we all got breakfast! (I don't know if that's weekly or not)

My training is over and my first week as a salesman starts tomorrow. If I don't get any sales I'ma quit and find another job lol. If I do get sales I'll hopefully gain enough clout to start picking up chicks.

Thinking back on Wednesday, that day I spent training with my hot boss, I think I did a good job hitting on her enough to count as flirting but not so much that it's a HR violation. I think she subtly implied she's not interested. I'm thinking I gotta become a top salesman like she is before I have a shot.

Also I feel like a lot of the guys in the office are taller and more muscular (and obviously have more money) so I may be low hanging fruit at the moment. Maybe I gotta put a pin in my hair brained schemes for the moment and focus on becoming an excellent salesman first. (Or maybe everyone just has to know me better)
 
Last edited:

devilkingx2

Master Don Juan
Joined
Jul 9, 2013
Messages
4,546
Reaction score
2,243
Location
NYC
Also all of my favorite bosses at all of my jobs have been mid 30s but still pretty Latinas who are very nice. I wonder if i have a fetish lol.
 

SW15

Master Don Juan
Joined
May 31, 2020
Messages
13,531
Reaction score
11,393
Also all of my favorite bosses at all of my jobs have been mid 30s but still pretty Latinas who are very nice. I wonder if i have a fetish lol.
Mid 30s Latinas are usually single moms. Latinas become moms earlier in life than white women.

When 30+ childless men want to date 30+ childless women, that's usually white women.

There are few things more annoying than a careerist Hispanic/Latina woman.
 

zekko

Master Don Juan
Joined
Aug 6, 2009
Messages
16,076
Reaction score
8,926
Thinking back on Wednesday, that day I spent training with my hot boss, I think I did a good job hitting on her enough to count as flirting but not so much that it's a HR violation. I think she subtly implied she's not interested.
I was going to say that if you wanted to pursue this, I would try to get her out doing something but definitely wouldn't frame it as a date, just a casual after work thing. Then maybe something can "just happen". Sounds like it's too late though. If she has three kids she's probably too busy to do any hanging out anyway.
 

Sam_J

Don Juan
Joined
Apr 14, 2021
Messages
164
Reaction score
105
Age
28
I fukked my boss but she was three years younger. Years ago, we were both in our 20s. Banged her all over the office. I hated that job so it was kind my way of getting some satisfaction. She was hot and I knew it would happen eventually when she interviewed me.
How did you know from the interview?
 

It doesn't matter how good-looking you are, how romantic you are, how funny you are... or anything else. If she doesn't have something INVESTED in you and the relationship, preferably quite a LOT invested, she'll dump you, without even the slightest hesitation, as soon as someone a little more "interesting" comes along.

Quote taken from The SoSuave Guide to Women and Dating, which you can read for FREE.

devilkingx2

Master Don Juan
Joined
Jul 9, 2013
Messages
4,546
Reaction score
2,243
Location
NYC
Mid 30s Latinas are usually single moms. Latinas become moms earlier in life than white women.

When 30+ childless men want to date 30+ childless women, that's usually white women.
Hmmm that's good to know actually. I can refine my targets accordingly!


There are few things more annoying than a careerist Hispanic/Latina woman.
Single moms and careerist women are both turn offs for me. Lots of responsibilities and not much free time. That's why I gotta make sure to keep things casual if I manage to smash my boss or any other MILF.

I was going to say that if you wanted to pursue this, I would try to get her out doing something but definitely wouldn't frame it as a date, just a casual after work thing. Then maybe something can "just happen". Sounds like it's too late though. If she has three kids she's probably too busy to do any hanging out anyway.
There was a part of the day that went something like-

Her: (mentions that she's single and not looking for anyone right now)

Me: (wondering if that's a good sign because she volunteered her relationship status)

Me: oh yeah I know what you mean, I'm not too big on jumping into anything serious. I just want to find someone to have fun and party with.

Her: well I hope you find someone like that!

Me: oh yeah, me too.

Later on I overheard a rumor from one of the other guys that she had a date on Friday.

But that's definitely a good idea Zekko, I'm gonna try that later on when the situation shifts into my favor.
 

SW15

Master Don Juan
Joined
May 31, 2020
Messages
13,531
Reaction score
11,393
I fukked my boss but she was three years younger. Years ago, we were both in our 20s. Banged her all over the office. I hated that job so it was kind my way of getting some satisfaction. She was hot and I knew it would happen eventually when she interviewed me.
The few times that I have had an attractive female interviewer, it was usually a1st round HR type interview. HR representatives have a tendency to be younger females and some are attractive.

If you're ever dealing with a 3rd party recruiter (a recruiter contacts you from a company that isn't the hiring organization), those women are usually attractive. It's a sales job (more so than a corporate recruiter) and attractive women are often hired in sales roles.

Female hiring managers are usually not as attractive as corporate/third party recruiters. I can't recall an instance in my career where I had an attractive female interviewing me for a job in a management type role.

I prefer that my immediate supervisor is a man. Female bosses are usually bad news. I have had a beta biatch boy as a manager once and another incompetent male as a boss.

In most white collar jobs, even if your direct supervisor is a man, there are usually women in executive management that will be a part of your interactions.

In my jobs in the past 10 years, I have not had any top tier, attractive female co-workers. I've had cute female co-workers, but I wouldn't jeopardize my white collar jobs for a woman I'd rate as a 5.5-7. It's tougher at about 7.5 or 8 on your own rating scale to turn down an attractive co-worker or manager.

I don't seduce at my workplace. If I didn't work white collar, I might be more inclined to seduce at work.
 

TheCharmingGuy

Senior Don Juan
Joined
Nov 19, 2020
Messages
328
Reaction score
273
Age
27
Location
North Carolina, US
Possible? Of course. Desirable? A single mom who controls your employment status? Definitely not. The fact that she is a single mom alone should be a big red flag.
 

Peace and Quiet

If you currently have too many women chasing you, calling you, harassing you, knocking on your door at 2 o'clock in the morning... then I have the simple solution for you.

Just read my free ebook 22 Rules for Massive Success With Women and do the opposite of what I recommend.

This will quickly drive all women away from you.

And you will be able to relax and to live your life in peace and quiet.

biggoal

Banned
Joined
Jul 19, 2019
Messages
3,696
Reaction score
798
Age
40
Hmmm that's good to know actually. I can refine my targets accordingly!




Single moms and careerist women are both turn offs for me. Lots of responsibilities and not much free time. That's why I gotta make sure to keep things casual if I manage to smash my boss or any other MILF.



There was a part of the day that went something like-

Her: (mentions that she's single and not looking for anyone right now)

Me: (wondering if that's a good sign because she volunteered her relationship status)

Me: oh yeah I know what you mean, I'm not too big on jumping into anything serious. I just want to find someone to have fun and party with.

Her: well I hope you find someone like that!

Me: oh yeah, me too.

Later on I overheard a rumor from one of the other guys that she had a date on Friday.

But that's definitely a good idea Zekko, I'm gonna try that later on when the situation shifts into my favor.
Why is it all I see on OLD is single moms?
 
Top