[HagansAvenue]

Putting this in the "Newbie" Forum because, in the end, I'm asking about one specific woman...

Background: Soon-to-be former client. She's 13 years older. Recently divorced. We've always gotten along really well. Everyone at my company jokes that she's into me like that and--while that's possible--my gut says it's more of a mother/son vibe than a bang vibe.

A lot of fun, light conversations over the 9 years we've worked together (me as vendor/ her as client). At the same time, we've both kept it professional re: sex, etc. I'm moving soon and set something up in a few days to hang out/spend time.

^Before I get into the pros/cons... my game is solid. Late thirties and never dated a woman over the age of 30. Above average looks.

This would probably be the last time we see each other for the foreseeable future.

Pros:
She offered for me to come by her place prior to us going anywhere. She texted the address and unit number
Recently divorced
We had a random site visit to her company (me and three other dudes) and--apart from saying "see you later"-- didn't mention a word about our meeting... only the both of us know.
It's been a running joke at our company that she wants to bang
I mentioned that I'd make a reservation for place after I come by her apartment, but we can "play it by ear" after I stopped by and she was just like texted back "Thanks." aka "we won't be leaving my place" (or she's not the best texter... even for logistics)

Cons:
She could totally see this in the complete opposite... he's so nonthreatening that I could invite him over
Fun banter, but professional throughout our time knowing each other (even though this is how we both are and wouldn't get "weird" like that)
I totally set all of this up (even though she made the apt invite unprompted)
It's likely not going to be a drinking situation (which, all things considered, is for the best)

^Basically, confirmation bias could have me seeing something that's not there.

Despite starting a thread about this, my whole outlook is to go, have a fun, and not fuss about banging.

I also understand that--within reason--if a woman is willing to meet you out, then sex is on the table.

Just looking to get some thoughts and other perspectives about this. To preempt any "don't shit where you eat" responses, I'm leaving so soon that this won't affect work at all. We do not work at the same company.

[kaotic]

You're in your late 30's and shes THIRTEEN years older than you, she has kids, AND she got divorced.

Sounds like a prospect I'd want to avoid.

Besides the don't shit where you eat - she can be a pivot for me - as in she has friends to bang or clients to forward you or business networking.

Now, let's talk about the scenario - you're wise to know it could be one of two ways to view you.

Oh he's harmless or the oh I might fuck him.

It's your job to pick up on her cues/body language/etc

Just go into it with an open mind, a good vibe, and flirt a little bit, see where it takes you, if she's receptive, escalate.

[Akwesi]

Above average looks... compared to other 50-year-olds? Unless your date is Halle Berry this sounds fucked up.

[treypound]

(01-17-2018 01:52 PM)kaotic Wrote:  

You're in your late 30's and shes THIRTEEN years older than you, she has kids, AND she got divorced.

Sounds like a prospect I'd want to avoid.

Besides the don't shit where you eat - she can be a pivot for me - as in she has friends to bang or clients to forward you or business networking.

I have seen this scenario play out bad for many guys in my adult life. 2 friends (in our 20s) banged their bosses (who were married in their 30s). It was all fun and games until (in one case) - HR found out and fired the man, and (in another case) the hubby found out and showed up to work ready to fight.

A nearly 50 yr old woman, no matter how hot, with all the above red flags, should be avoided. You likely won't heed my or others advice, so enjoy it and hope it works out.

[HagansAvenue]

I appreciate that responses.

I'm leaning towards a non-sexual vibe with all of this... which, all things considered (and as everyone above knows), is for the best.

It really could go either way... as said below, I'll see the vibe.

[Beirut]

Well you are attracted to her (or not, its not up to us to decide)

Shes inviting you to her place. I dont think its because she views you as nonthreatening. Thats quite rare because a nonthreatening guy is a waste of evening. But anyway, you can see the vibe when you get her.

You set the whole thing up. Well youre the man so youre supposed to.


Theres nothing here to think over or overcomplicate.

^^^^ hes leaving the city soon so all these red flags dont matter.

[General Stalin]

Feel out the vibe and go with your gut. After all, after tonight you will no longer be involved with her professionally, no?

Bring a bottle of wine to her apt.

[HagansAvenue]

"^^^^ hes leaving the city soon so all these red flags dont matter."

That's correct... new career, new location, and I won't be involved with her professionally after that night.

[Jetset]

1) A fit, attractive new divorcee at 45-50 is going to be in cock destroyer mode. I've seen it. It's terrifying. If everybody has picked up on her wanting to bang, she doesn't want you over because she thinks you're harmless. You may not even be her first colleague today.

2) You don't know how crazy she might actually be. Maybe she wants to piss off her ex-husband. Maybe she's divorced because she's going bananas with mid-life hormones. Maybe she will try to burn your life down when it doesn't work out and she realizes she's not 25 anymore.

Choose wisely. Wrap it up if you do.

[Bienvenuto]

This sounds like 'fools mate'.

Get the notch. Willing to bet she brings a creative role play/ dominatrix vibe on the night.

Enjoy

[General Stalin]

Has this meeting already happened? What was the outcome!?

If not, keep us posted.

[Vaun]

dude you sound totally desperate, like you can't get laid with more appropriate women. And I'm not just talking about her age.

Apart from the desperation, this will sink your career. People talk. They will tell your future employer. Your colleagues now will tell your future colleagues. Your boss and the leaders of your current company will look down on you. What happens if you end up working with the same people in a new company?

I wouldn't trust you with my clients if I found out about this, most likely neither will anyone else in your industry.

Too much down side here. You're willing to throw away your career for some, dry, old dusty pussy?

The thing is, you want to keep her begging for it, without ever giving her the dick. That way, you get references, favors, new jobs, etc. The second you fuck and she then dismisses you, you can kiss that goodbye, just like she did her husband. You want to use her, but not for a nut.

I wouldn't do this chick if she were 13 years my junior and a UFC ring girl.

You will destroy your career by sticking your dick in grandma.

[Jetset]

Personally, I agree with Vaun. This is the kind of game I run at work. Women who show an interest get attention and validation for being my cheerleaders, not fuckbuddies. Some of the nominations I get for company awards, you'd think I had impregnated them.

If you're staying in this industry at all, work-wifing her up is likely a better investment. Do what you want, tho.

[HagansAvenue]

This will all happen on Saturday and I’ll post an update over the weekend or Monday at the latest. I’ve seen too many threads where dudes ask for advice/perspectives and don’t post a follow up.

She’s been a cheerleader-and-half throughout my time here. There were some changes on her company’s end so we saw less over each other over the past 12 mos. I understand that sexual tension greases the wheels of commerce and, as of now, that may have been the dynamic... though I’ve always thought it was more mother/son than “let’s fuck..”

I’m pretty sure the husband bailed on her though.

I’m going to be in a new location with new career in a different industry... so realistically there won’t be any overlap.

Just to clarify, the 13 years+ lady is attractive to me. At the same time, I have plates that much younger... So it’s not quite about thirst in that way.

^ I understand if that makes this all sound even weirder. The main thing is I’m trying to get a read on this before I go and the perspectives have been helpful.

I’ll see the vibe and go with it. I appreciate the responses—it’s been a tough thing to get a read on—and will follow up.

[Vaun]

(01-18-2018 10:28 PM)HagansAvenue Wrote:  

I’m going to be in a new location with new career in a different industry... so realistically there won’t be any overlap.

What about your recommendations and referrals from your former company? You're old enough to know those relationships last decades. It seems like you might be building this up in your head. This happened to me last year. We built it up for over 10 years. We got together, had good sex, and never talk to each other, at all anymore. To be honest, I'd rather want her friendship than the bang now. Even though we have had the hots for each other since 2005.

[HagansAvenue]

(01-19-2018 10:27 AM)Vaun Wrote:  

(01-18-2018 10:28 PM)HagansAvenue Wrote:  

I’m going to be in a new location with new career in a different industry... so realistically there won’t be any overlap.

What about your recommendations and referrals from your former company? You're old enough to know those relationships last decades. It seems like you might be building this up in your head. This happened to me last year. We built it up for over 10 years. We got together, had good sex, and never talk to each other, at all anymore. To be honest, I'd rather want her friendship than the bang now. Even though we have had the hots for each other since 2005.

I hear you. I wouldn't have made the thread if--barring some crazy false-rape accusation-- this would affect how I earn money, my soon-to-be former employer, or anything like that. Different industries, different regions... it's a complete severing of ties.

You're right, I'm totally building it up in my head. If I had to bet, I would bet that it will be platonic and chill.

[Baphomet]

(01-19-2018 12:28 PM)HagansAvenue Wrote:  

I hear you. I wouldn't have made the thread if--barring some crazy false-rape accusation-- this would affect how I earn money, my soon-to-be former employer, or anything like that. Different industries, different regions... it's a complete severing of ties.

You're right, I'm totally building it up in my head. If I had to bet, I would bet that it will be platonic and chill.

Which begs the question:

Why on earth would you waste irreplaceable time, for a "platonic and chill" gab session with an over-the-hill woman whom you'll never see again?

Sign me,

Baffled.

[Jetset]

(01-19-2018 02:40 PM)Baphomet Wrote:  

Why on earth would you waste irreplaceable time, for a "platonic and chill" gab session with an over-the-hill woman whom you'll never see again?

Whatever you do, don't buy her an appetizer, OP.

[HagansAvenue]

Baphomet,

Because it's been a great working relationship, I learned a lot from this lady + she always cheerlead'ed me. Whatever goes down/doesn't go down - I'm glad to see her before I go.

Again, the whole idea with starting this thread was to get some different perspectives because I've never encountered a situation like this.

RE: appetizers Haha. Never will I ever.

[HagansAvenue]

TL;DR no +1 and I appreciate you guys for the reality-check perspectives:

Ok so i get there and she makes strong margaritas. Touching, the word “sex” is mentioned more than once, and eye contact that told me all I need to know.

^ Green lights all over the place.

Buuuuuut man I appreciate you guys: Could doesn’t necessarily mean should. I’m reliving this thread in my mind and I consciously let the conversation wander a bit... the whole thing seemed off (can’t imagine why... Heh)

Quickly it turns to ex-husband stories. Plus, her most recent boyfriend bailed for another woman.... she went by his JOB today and gave him some sort of gift haha but “now she’s over it...”

Red flags quickly outnumbered the green lights.

I let her talk herself into seeing me as a platonic good guy. Unfortunately I was a little faded, cops are everywhere in my part of the world, and I was tired. We crashed in separate beds.

Here I thought I was Mr. Fast Love...and sometimes I am, but not with this one.

If it wasn’t for this thread I would’ve steered it in a different direction. Maybe it would’ve been fine, but I had no desire to take the chance.

Thank you. I didn’t buy appetizers.

[Jetset]

(01-20-2018 06:27 AM)HagansAvenue Wrote:  

Quickly it turns to ex-husband stories. Plus, her most recent boyfriend bailed for another woman.... she went by his JOB today and gave him some sort of gift haha but “now she’s over it...”

Red flags quickly outnumbered the green lights.

Yeah, you probably dodged a bullet there.

I'm not going to criticize anybody for having an older woman pass their boner test, but if she's single, there's typically a reason. It might be "bitch is crazy", and nobody needs that showing up at work. You don't even know if this guy was really her "boyfriend", or if she was just a plate and didn't accept it.

[Vaun]

I think you got the best result out of this you could have wanted. She still adores you, but you wont incur the wrath. Always leave them thinking you are better than them. She threw the work thing out there unconsciously, fuck with her and your old work colleagues will find out. I don't judge either for the age, I was just in Vegas and I'd rather date 46 year olds there than 28 year olds in SF, Seattle, Boston and most American cities.

[General Stalin]

Admire your resolve to resist the urge.

I would have smashed for sure.

[RatInTheWoods]

SHould have banged.

Old MIlfs can be mind blowing.

[Dulceácido]

Unless you get another chance and correct this, you'll regret not fucking her for the rest pf your life.