Dear Luv Doc,
A few months ago I met a man through a dating site who checked all the boxes. He is a good-looking silver fox type, long divorced, recently retired, has a paid-off home in West Austin, has a nice car, and as far as I can tell his retirement income allows him to travel, go to nice restaurants, concerts, etc. without worrying about the cost. I, on the other hand, still work a 9-5 job, have a mortgage, bills, a car payment, and two adult children who occasionally need financial help from time to time. We really hit it off at first, went on several dates, had great conversations, sex, etc., but I was having a hard time keeping up with all our activities while still trying to work a job and get a decent amount of sleep. I suggested we try to limit our dates to the weekends – or at least try to limit our weeknight activities to once a week. He seemed to take this in stride but after a few weeks he became frustrated and began complaining about the limitations I placed on our relationship. Another thing that changed was that he started offering unsolicited advice about my job, how I parent my children, and even what I was wearing on occasion. Our conversations have become less of an exchange of thoughts and ideas and have started feeling more like an unwanted mentorship. I will admit that I am somewhat intimidated by his financial success and his carefree lifestyle and that I might be feeling a bit defensive, but I don’t like how the dynamic has shifted away from an equal partnership. I would hate to mess up a good thing because it’s been a while since I have dated a man for more than a short time. Do you think I am being overly sensitive about our difference in income and lifestyles? Or should I end this before he gets worse?
– Fiftyish Working Mom
I don’t know. It seems to me that you know what your priorities are, have your shit together, and are proceeding cautiously while noting some obvious red flags. I should probably temper the preceding by saying that as a grossly unprofessional advice columnist, I’m not sure I have a really clear sense of the point at which it’s appropriate to weigh in with advice and opinions with anyone – solicited or not. I mean, I get it. I understand the gig. I know that ambiguity and prevarication don’t butter the Chronicle’s bread, but no matter how bombastic and opinionated I may come across in the name of engaging prose, I don’t consider myself to be some sort of self-help guru or sage. I don’t think my friends would say I’m constantly showering them with hot tips. OK, I did recently advise my friend Marcus that he should become a televangelist, but that was because I think he could make some sick scrilla hawking eternal salvation on the TV. I also still need a friend with a private jet. I just don’t feel safe flying commercial. Like the Right Reverend Kenneth Copeland says, I ain’t trying to get “into a tube with a bunch of demons.” So you see? If anything I’m plagued by even more neuroses than the average person. I just have the unique privilege of working them out in print every week.
I know a couple of months may seem like a lifetime in the modern dating world, but no matter how quick a study this dude is … no matter how immediately insightful he might be about the human condition, he is still, in my opinion, in the learning stage of your relationship. If I may phrase that a bit more coarsely, he needs to shut the fuck up and really get to know who you are, what you’ve been through, and where you come from before even approaching the gall to weigh in on what you’re wearing – much less how you live your life, conduct your business, or parent your children.
OK, now that I’ve gotten that off my chest, I should point out that just because someone has experienced financial success doesn’t necessarily make them an expert or authority on anything. Elon Musk is currently the richest man in the world. He might be a genius at running companies, but he’s proven himself to be an absolute fucking idiot in every other aspect of his life – and I’m not just saying that because he supported an openly corrupt, lying imbecile for president, but it’s some irrefutably damning evidence. So this fellow you’re dating seems to possess a disturbing amount of hubris as well. Feel free to proceed, but proceed with caution. Your spidey senses are probably right.
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This article appears in February 6 • 2026.