Some Women Have a Sense of Entitlement

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DEAR MIDLIFE BACHELOR:  I’m a 45 year-old professional man who has been dating a 43 year-old professional woman for several months.  We both earn well over $100K/year.  Unless it’s my birthday, or I won a bet and she owes me, I always pay the bill — lunch, bar tab, dinner, tickets of any kind,  travel, etc. — even if where we are was her idea.  I have raised the issue, and she falls back on being “an old fashioned girl.”  To me, this is a double-standard — she enjoys and embraces all the benefits of modern womanhood (opportunity, career, income, etc.) but holds on for dear life to the “benefits” of the days when women were seen as little more than the weaker sex.  I think this “he who has a penis pays the bill” attitude is BS.  I think there should be some “ability to pay” aspect and some equity.  Am I being unreasonable?  Am I out of the mainstream?  Am I destined to be alone if I don’t change my opinion?  Thanks.  Dave, 45 years old, Orange County, CA

MLB ANSWER:  Hi Dave – you are not being unreasonable for wanting your $100K/year girlfriend to help pay for dating expenses.  Regardless of their income level, many women today have a sense of entitlement – which means they expect you (the man) to pay for everything.  Some subset of these women will tell you with a straight face that they are “traditional” or “old fashioned” women … and actually appear self-justified.  When confronted with such attitudes in the past, I have wondered how these traditional/old-fashioned women would react to me proposing they clean my house?  Or cook me a meal?  No – you cannot SAY that sort of thing out loud that because you know her response would be less than ideal.   You see, being a “traditional” or “old fashioned” woman has a very narrow definition in today’s society.

I have dated a high income earner woman who was probably worse than your girlfriend in terms of her sense of entitlement.  She would have me take her out for these $400 evenings … most of those bills were related to the wines she chose.  After a month or so of going out with her once or twice a week, I realized that she was going to break my bank – and that I needed to make a decision … because I could have been dating a handful of normal women for that same price.

The crazy hot Latina nurse I dated (discussed throughout this site) was the opposite though – she earned a pretty decent income, and paid for stuff probably about one-third of the time.  That was nice of her – she was pretty grounded in terms of the expense of dating, and willing to contribute.  My point – there are different types of women out there … some with less of a sense of entitlement.  It is hard to screen for that quality up-front without sounding cheap.

Dave – you live in Orange County, California … a place I spend a fair amount of time in currently.  I jokingly sometimes refer to OC as “Silicone Valley” because of all the aftermarket breasts I see … particularly in the Newport Beach area.  My point – you live in a very fluffy part of the world where there are a lot of trophy women.  [Trophy women are women who are extremely good-looking, and who expect to be well taken care of.]  Many of my former girlfriends have been trophy women – there is nothing wrong with them.  If your girlfriend is a trophy, it may be difficult to escape the financial role you describe.  Your only other choice is to move on, and take your chances with someone else.  For me, one thing that can immediately push me in the direction of flight is when a woman overtly tells me things like “dates are a free meal” or “I always eat for free”.  In other words, a woman with a blatant sense of entitlement gets kicked to the curb in a hurry by me … not for feeling entitled, but for being dumb enough to bark it out.  Good luck – let us know if you are able to negotiate anything with your Orange County girlfriend.

DEAR MIDLIFE BACHELOR:  I just want to get your opinion on a situation I have here.  I am 40, have been divorced for the past seven years, and I live with my girlfriend, and have done so for the past year and a half.  We get along great, and she is great in bed.  For the past two months, I’ve also been having sex with a younger married woman who works in my office.  We’ve knocked it out first in my car, then in her car – and we have graduated to a hotel room the last couple of times.  Neither me or the younger woman from work want a relationship with one another – but we enjoy the sex.  What is your take on this exactly?   Steve, Age 40, Mountain View, CA

MLB ANSWER – your love triangle situation is certainly interesting, and to an extent you are living the midlife bachelor dream!  The biggest problem in my opinion is that the younger woman you are fooling around with – she is married … and that is definitely a bad karma situation for you.  You are also creating bad karma by cheating on your girlfriend … but since she is your girlfriend, and not your wife, then that is up to you.  I can tell you that the more recent love triangle situation that I was involved with – everything wound up turning to shit!  Neither woman was married – but I chose incorrectly, wound up getting dumped, and then later recognized what poor choices I had made based pretty much on the hotness of the woman involved, and the extremely good quality of the sex we were having.  “The hottest fires burn out the quickest” – that expression was definitely true for me in that case.  All I can tell you is that eventually things will return to equilibrium in your life – and you will hang on to the memories and lessons of your current dilemma.  Enjoy it as long as you can, and let us know what happens!   Oh – to reference a few things on this site to read, you might check out Is Cheating Worth It?  Or maybe if you think there are “short shelf life issues” in your relationship with the woman at work, maybe checkout The One Night Stand at Midlife.  In terms of dating advice, you don’t seem to have a problem getting dates … so maybe I’ll recommend you read the section entitled Reaching Midlife Bachelor Equilibrium.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.