Dating Challenges of a High Income Woman

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DEAR MIDLIFE BACHELOR: I challenge the notion that earning a high income is positive for a woman. I am 45, and have been divorced for two years – so I’ve been back in the dating scene again for a year or so. I have a fairly high income, well at least it’s higher than most men I have met recently. I live in a very expensive city where most people live in apartments/condos. I have two kids and a rather large house. I usually meet first dates out at restaurants and if the date goes well I accept a ride home. I get lots of comments on the house like, “You live here … wow, my apartment would fit in your living room!”, etc. I get lots of uncomfortable jokes about it (I don’t make THAT much – just more than most guys do). I have two nannies, and I often get jokes about my “staff” … or they ask me if I am taking my ten maids on holiday … you get the idea. I don’t get lots of second dates, and silly me I think the two things are related. (Did I mention I am thin, long-legged, and yes I even Brazilian wax) so I think I should be able to get a repeat a bit more often than I do.

Although I try to stay positive, I do find this a bit discouraging as I feel that if I were a man, my income would be a huge asset as the high income guy is often the toast of bachelorhood. I can’t buy a date, although I actually haven’t tried to buy a date … but maybe I should since apparently I can afford it.

I am considering lying about my job (I never bring it up, but I often get asked) and never taking a guy by my house etc. I think men say they like successful women, but in reality they only want them if they are less successful than they are. Just my experience – I’d welcome your opinion. Lexie, age 45

MLB RESPONSE: First of all – kudos to you on the Brazilian wax job. I find this highly entertaining, and speaking on behalf of all midlife bachelors I say, “Well done – we salute you!”

Now for a serious answer. I know exactly what you mean – a jackpot woman (see Types of Women – Jackpot) with too large an income can often be intimidating to a man. I personally make a lot of money – and in my lifetime I’ve been out with several women who buried me in terms of income. One had a lot of “old family money” … another was an M.D. with her own TV show … and another was a really successful divorce attorney. I always felt intimidated by these women … and I just couldn’t get past it. I felt like these women were somehow better than me or smarter than me … and they very well may have been. But the problem was that in my own head, I was not the leader of the relationship … like they were the one in the driver’s seat. I know that sounds dumb, but that is my best interpretation of it.  So I do sympathize with your dilemma.

So you can do one of two things: 1) Date men who make more than you, or 2) Date men who make less than you do. Often times, midlife men who make huge incomes ($350K+) become obsessed with chasing mid-20s bombshell “trophy” women. So depending on the man, it may be somewhat challenging to date someone who is at or above your income level. Recognize, however, that regardless of income, some of us (myself included) prefer women our age (mid-30s to mid 40s) just because there is no maturity gap. My point is – the pool of available men is larger if you focus on men who don’t make as much as you.

How do you date these men who make less than you without scaring them off? I’d say you minimize mention of how much you make … don’t take them to your big home … just generally keep any discussion relating to what you do for a living somewhat vague for as long as possible. I do this same thing pretty much all the time … with friends and acquaintances just because I cannot stand listening to people who brag about what they do or what they own, etc. So for me what I’m talking about comes fairly easy. The idea is that you put off exposing the man to your wealth until you are sure he is in the relationship for the right reasons … and then it can be more of a pleasant surprise.

Of course, you could do the exact opposite and go overt – Liza Minnella style … where you are clearly the boss of the relationship, and insist that the man serve you in every possible way. You might even get a mid-20s male model who caters to your every whim. And even if the relationship is superficial, it might just be a good ride for a while. Ha ha

No matter how you decide to proceed, or which type you decide to pursue – my advice is that you focus on staying positive … that you map out and stick with a strategy to meet the type of man you seek (see the section under Dating Advice entitled Develop a Strategy for Midlife Bachelor Success), and continually re-evaluate yourself, your objectives, and your methods and tactics until you have found the perfect man. I know – the Dating Advice section is written for a man from a man’s point-of-view … but you can adapt, not adopt, as much of it can be applied to men or women. Good luck – and thanks for sending in the photo, Ms. Jackpot Lexie!  You will be fine!!!

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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.