Dating an older successful woman

I have been dating different girls for the past year or so – but one of the girls I have dated during the past couple of months was a successful business woman – who is older than me – and things have started getting serious.

We are now in some sort of ‘relationship’, and I have slowly started sleeping with fewer girls as I spend more and more time with her. During the past couple of weeks I was left with only 2 girls (she was one of them) – but eventually I found her more intriguing and realized that I really like her personality the more I got to know her. I am still seeing the second girl, but it seems as if I am heading into a relationship here and will probably commit to the older girl.

However, the fact that she is very successful kind of puts me in an awkward situation. I know this might sound weird to some people on this board, but I am trying to succeed in my own business and the fact that she is much more successful than I am makes me feel inadequate. I have tried to brush those thoughts to the side, but the more I get into this relationship, the more I feel like I am losing my independence. Overall, she is an amazing woman and I can’t say one bad thing about her. Part of me wishes that I could just accept the fact that she is in a different place in her life than me and live with it.

I was just wondering if anybody out there dated an older more successful woman and was under the same kind of pressure. Just as a side-note – she doesn’t put any pressure on me whatsoever – she always wants to pick up the bill, buy me stuff etc – and I always refuse to accept her offers - it’s just me who is feeling that I am not as good as she is. I am just trying to get to the bottom of this… thanks for any responses.

As long as you are making her accomplishments and business success an issue by using comparisons, you will remain a "lesser" man.

Your age...her age?

Francisco d'Anconia said:

As long as you are making her accomplishments and business success an issue by using comparisons, you will remain a "lesser" man.

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I agree - but is that a normal thing to do? Is there a way to avoid making the comparison? Has anybody been in the same situation and managed to avoid making the comparison?

Think of it this way - you're in a swimming competition and you're just starting out. So far you've been trying hard to succeed - but you're still struggling and having a hard time making it into the championship. Now you're leaving with this person who's really successful, has already made it into the championship - how would you feel being around this person telling you about his achievements all day? It would be unfair for you to ask the other person to stop bragging about his / her winnings - beacuse that's the essence of his / her life - they have been working hard to win so naturally they will be proud of their winnings - and you should be proud and there to support them.

I know that it is probably me who is at fault - but I am just trying to analyze my reaction to the current situation and make a decision one way or ther other.

^ You're getting sucked into her frame.

YOUR frame is that she IS great and all, however on the downside she is also older and there are many younger, hotter girls for her to compete with too.

djzulu said:

Now you're leaving with this person who's really successful, has already made it into the championship - how would you feel being around this person telling you about his achievements all day?

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I'd feel inspired. I hang out with successful people every day. I stick with the winners. They hang out with me because I encourage them in their successes and congratulate them. In turn, they congratulate me on my successes. When someone close to me does well, I feel happy for them. It sounds as though you've never been around a successful person and don't know how to handle it. Successful people have amazing things happen to them - things that would sound like bragging to someone else, but they're just telling you about their life.

Just tell her good job and keep up the good work. Be genuinely happy for her -- if you can't, then get out of the kitchen.

Older, "professional" women aren't your problem. This is your problem:

djzulu said:

,.. I have slowly started sleeping with fewer girls

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and more importantly this:

djzulu said:

but it seems as if I am heading into a relationship here and will probably commit to the older girl.

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Sweet Mother Mary, how the fukk do guys come up with sh!t like this? If you are typing stuff like this after 2 WEEKS (?!) of talking to this woman, you've got a bigger problem than silly perceptions of a gap in 'professionalism.' Committment isn't something you should be planning for, it should hit you over the head unexpectedly after you held off until the last moment.

Your problem is you lack real options and this older 'gal' seems like she'd be easy pickin's (and probably true at her age), right? I mean why risk rejection with younger, hotter women when you've got the sure bet here 'eh? Her conditions are she's not getting any younger and she's not as sexually marketable so she makes herself more accessible, and your conditions are you're out of options and she seems like the path of least resistance.

Rollo Tomassi said:

Older, "professional" women aren't your problem. This is your problem:


I mean why risk rejection with younger, hotter women when you've got the sure bet here 'eh? Her conditions are she's not getting any younger and she's not as sexually marketable so she makes herself more accessible, and your conditions are you're out of options and she seems like the path of least resistance.

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Rollo - you totally got it wrong.

I have been seeing this girl for 4 months now - I have just been seeing other girls at the same time - was dating 5 girls at the peak. However, I connected with her better than I did with the other ones - that's why I started spending more time with her. I have dated 20 y/o to 40 y/o and I find that it's much better hanging around her - I have managed to develop feelings for her.

I have been getting enough a$$ for the past couple of years - and I have never met a girl of her caliber.

Latinoman said:

Your age...her age?

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Early 30's Late 30's

wayword said:

^ You're getting sucked into her frame.

YOUR frame is that she IS great and all, however on the downside she is also older and there are many younger, hotter girls for her to compete with too.

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I agree - she's older and has much more competition - but does that mean that I have to stick around younger women for now?

djzulu said:

I agree - but is that a normal thing to do? Is there a way to avoid making the comparison? ....

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Remember, AFC's do the things that are "normal." The only way to avoid making the comparison is to be genuinely happy with who you are.