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Help a mature brother decide

spred

Don Juan
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Hello, long time member and reader. Can't post in Mature man so I ask here.

Me: 44, not married, no kids, very good job, leadership positions in big companies (good social value)
Her: 40, not married, no kids, good looking, workaholic, leadership positions in manufacturing.

Met online 1,5 years ago, at the time I was working in another city. Exchanged expectations (no kids, contact info). Spoke daily on her initiative over phone or messaging,she is very open and talkative. Met after 3 months at her initiative (I asked her out, she preempted and suggested earlier date). Offered info about her job, family, issues, intimate stuff. Kept asking about when we meet when I am in need town, initiated 90 percent of contact. Asked me after one date to spend weekend with her family, I didn't take it up. Keeps describing her day, offers support, offers to cook my fav food, tells me when she meets guy friends. Keeps making sexual jokes. Met second date helping her out with an errand, invited me over to her for coffee.
Overall she is invested , I am not.
Here is the issue: I suggested we spend New years together, she declined because she had family over (legit situation). After she told me that a male friend picked up her parents for the party at her place, and the guy spent the day with her and family. I suspect old boyfriend.
She is trustworthy, kept all her promises, offers details on how she spends her time, I have no evidence to the contrary.

Red flags: all our dates happened on her terms (locations and timing); has only male friends (1 orbiter and 1 old BF).

Dillema: stick around to find out what's the story or cut my losses? She has all to lose, me nothing.
Or I am seeing things which are not real?
Thanks
 

Knight of Roses

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Too old. Why you going after 40 year olds at 44?
I’m 35 and I date typically in 20-25 yo demographics. You shouldn’t be seeing anyone above the age of 32 IMO
 

spred

Don Juan
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Too old. Why you going after 40 year olds at 44?
I’m 35 and I date typically in 20-25 yo demographics. You shouldn’t be seeing anyone above the age of 32 IMO
She has all except age: good looking, not playing games so far, good financial, taste in clothes,furniture, very high interest, zero drama, zero flakes

I know what you are saying, at 44 I should date max 44/2 plus 7, meaning 29 :)
 

Bethatsocialguy

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The problem is, she is making all the decisions in her personal life as well as her work life and you are allowing it to happen. Deep down, she doesnt want to be making those decisions in her personal life but she is so used to it (aafter all years working) that she does it now and no guy has come along and been the leader for her. I honestly think you can do better. The age is a big issue and I think that her mindset is fixed and you wont be able to change it. It is going to lead to more headaches in the future because her dominance is going to want her to be in a leadership position in whatever you have with her. You say 0 drama and 0 flakes now but you are not in any type of relationship with her so you cant confirm whether this will be the same when the situation changes (chances are it wont)
 

Kotaix

Master Don Juan
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There's nothing wrong with dating women in their 40s. They tend to be raised better than younger women. If she turns you on, she turns you on.

OP, I'd say give it a shot because she's so high interest. Just keep your eyes out for signs of crazy.
 

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Modern Man Advice

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Hello, long time member and reader. Can't post in Mature man so I ask here.

Me: 44, not married, no kids, very good job, leadership positions in big companies (good social value)
Her: 40, not married, no kids, good looking, workaholic, leadership positions in manufacturing.

Met online 1,5 years ago, at the time I was working in another city. Exchanged expectations (no kids, contact info). Spoke daily on her initiative over phone or messaging,she is very open and talkative. Met after 3 months at her initiative (I asked her out, she preempted and suggested earlier date). Offered info about her job, family, issues, intimate stuff. Kept asking about when we meet when I am in need town, initiated 90 percent of contact. Asked me after one date to spend weekend with her family, I didn't take it up. Keeps describing her day, offers support, offers to cook my fav food, tells me when she meets guy friends. Keeps making sexual jokes. Met second date helping her out with an errand, invited me over to her for coffee.
Overall she is invested , I am not.
Here is the issue: I suggested we spend New years together, she declined because she had family over (legit situation). After she told me that a male friend picked up her parents for the party at her place, and the guy spent the day with her and family. I suspect old boyfriend.
She is trustworthy, kept all her promises, offers details on how she spends her time, I have no evidence to the contrary.

Red flags: all our dates happened on her terms (locations and timing); has only male friends (1 orbiter and 1 old BF).

Dillema: stick around to find out what's the story or cut my losses? She has all to lose, me nothing.
Or I am seeing things which are not real?
Thanks
That is a question only you know the answer to. You don't seem too enthused about this girl so why spend the energy and resources? But only you know how you feel.

As a rule of thumb, if you are not feeling it, don't waste your time/energy/resources. Especially at your age, you have to be more intentional with the people in your life.

My two cents.


Modern Man Advice
 

spred

Don Juan
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I am feeling it a lot, it's just too good to be true based on my dating experiences. You are correct regarding being more intentional, I will act on your feedback. Thanks a lot.
 

BackInTheGame78

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She has all except age: good looking, not playing games so far, good financial, taste in clothes,furniture, very high interest, zero drama, zero flakes

I know what you are saying, at 44 I should date max 44/2 plus 7, meaning 29 :)
Have you banged this woman yet? Your OP doesn't make it clear. I would certainly hope so after 1.5 years.
 

BeExcellent

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Have you banged this woman yet? Your OP doesn't make it clear. I would certainly hope so after 1.5 years.
That’s my question too. If the answer is no what you are is an orbiter and what y’all are is pen pals.
 

spred

Don Juan
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The problem is, she is making all the decisions in her personal life as well as her work life and you are allowing it to happen. Deep down, she doesnt want to be making those decisions in her personal life but she is so used to it (aafter all years working) that she does it now and no guy has come along and been the leader for her. I honestly think you can do better. The age is a big issue and I think that her mindset is fixed and you wont be able to change it. It is going to lead to more headaches in the future because her dominance is going to want her to be in a leadership position in whatever you have with her. You say 0 drama and 0 flakes now but you are not in any type of relationship with her so you cant confirm whether this will be the same when the situation changes (chances are it wont)
You are absolutely right.
I've been thinking back at our interactions and message history over the past year.
Conclusions:
- all the interactions (messages, phone calls, dates) that I initiated were countered and made happen on her terms (timing, location, sequence).
I have tested this yesterday: messaged her to let her I know I will call her to discuss something important, she called me one hour earlier than my proposal; I proposed a firm date for weekend (time and location), she agreed but spent 30 minutes"convincing" me to change time and location to another place she likes (and took me before there).She also requested me to confirm the date just before. I will reiterate my terms Saturday and accept no change.
Also by checking the message history I found out she invited herself over to me in two ocassions, at the time I countered because legit reasons.

Regarding interest, there is a big difference between messaging (caring, sexual, funny) and in person interaction (cold, hesitant). All physical contact was initiated by me, and accepted.

Overall I came to the conclusion she is gaming me and controlling 100% of actions.

I tend to see it as a challenge and take control (lead her), regadless of outcome I will learn.
Opinions?
 
Last edited:

Glassguy

Master Don Juan
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You are absolutely right.
I've been thinking back at our interactions and message history over the past year.
Conclusions:
- all the interactions (messages, phone calls, dates) that I initiated were countered and made happen on her terms (timing, location, sequence).
I have tested this yesterday: messaged her to let her I know I will call her to discuss something important, she called me one hour earlier than my proposal; I proposed a firm date for weekend (time and location), she agreed but spent 30 minutes"convincing" me to change time and location to another place she likes (and took me before there).She also requested me to confirm the date just before. I will reiterate my terms Saturday and accept no change.
Also by checking the message history I found out she invited herself over to me in two ocassions, at the time I countered because legit reasons.

Regarding interest, there is a big difference between messaging (caring, sexual, funny) and in person interaction (cold, hesitant). All physical contact was initiated by me, and accepted.

Overall I came to the conclusion she is gaming me and controlling 100% of actions.

I tend to see it as a challenge and take control (lead her), regadless of outcome I will learn.
Opinions?
You are skating the question that several have asked.

Have you fvcked his chick or not?
 

Stoic

Senior Don Juan
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Personally, I would not be into a workaholic career woman. Aside from just having as a plate.

In my experience, they are just not good relationship material.
 

Stoic

Senior Don Juan
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Also, you should be leading. This is the issue with careerist woman. They are used to leading in the work place. Following a woman is no fun, even if you are getting laid.
 

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