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As a 33 year old male, I actually agree with the comments from the women here regarding the 50-something bachelor. When I ask a woman to spend some time with me, I ALWAYS make it something very casual - lunch, coffee, something relatively inexpensive...and then I always insist on paying 100% of the tab regardless of what she looks like or how well I think it went. This accomplishes three things - I avoid looking like a cheapskate, I have time to get to know the woman (the point, correct?), and she doesn't think I'm after something in particular. There were a couple times in my life when I spent too much on a first date, and I think the woman believed that's what was on my mind, when in reality I was simply desperate for a relationship & emotional connection with someone. A few years later, I made the opposite mistake - I didn't pay for her soda at a 7-11 that we stopped at while walking - not because I was cheap or didn't have the money, but because I was afraid she'd get it into her head that I was trying to buy my way into bed. (Fortunately the woman is still seeing me today, six years later.) I think the key is balance - and on 2nd & 3rd dates, be upfront with the woman - say that you don't have much money to spend...but only accept a contribution from her IF she offers - never ask for it - and ONLY if you're sure she will not resent you for it. If she is a respectable female (the kind you want), and not a gold-digger, she will understand and will value you for your time and attention, not your wallet. It's amazing that a guy 20 years my senior hasn't figured this stuff out.

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Re: Matt Thank you Matt for sharing your perspective. I hope the "gentleman" reads this. You give me hope regarding dating and that there are men of good character that are looking for a woman of good character. I am one of those women looking for a partner with more to offer than just his wallet.

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I just read this and HAVE to add my two cents. Before I married I had to turn down dates because I had no one to babysit my kids. Usually a family memeber would babysit but if they were unavailable I could not afford a sitter. Considering his age he could be dating women that need to have their children taken care of while on a date. He's resentful about paying for the date but has he ever considered that? In addition if a man were to ask me out for the first time I certainly would expect him to pay, afterall, HE asked ME. However, after that it should be a mutual decision. After the inital first date other dates can be dinner at home or even just popcorn and a movie on the couch. It sounds as if he's expecting these women to read his mind. If a man kept asking me out without any discussion about who's paying I would assume he could afford to foot the bill. If I were the one doing the askling I would pay of it would be dinner at my house or a park.

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I agree. He believes that only the hot supermodel types DESERVE to have their meal paid for. All the rest of you (and you should know who you are), that are sub-par, PAY UP! Or at least make sure you are well-read, have a sense of humor and can have a great conversation. If you miss on any of these, PAY UP! Maybe he should provide a checklist to his date so that he can make sure she meets all of his criteria before he decides whether he wants to pay. Especially if she is not pretty enough to persuade him to part with all of his money.

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As a woman, not a hot supermodel, who has met men through fix ups and dating services, I'll bet you Tired of Paying won't meet the right person because he's the kind of man who makes it clear that only the young and beautiful are worthy of his time and money as noted in his letter. Your advice about having coffee was excellent. If possible, I try to see if there's a way to have coffee and a walk for time and talking. Although I will say that even if we agree it's Dutch treat beforehand, all I've ever been allowed to do is leave a tip. I noticed he used the word "insist." Again, I'll bet plenty of women have offered to pay their share and he's demurred, then been mad at himself later. A little passive-aggressive?

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Dear Annie, Regarding the reasonably handsome 50 year old man wishing to share expenses on a first date. If a man asks a woman out, he may decide the restaurant, movie, play, museum, concert that will fit into his budget. If a woman asks a man out on a date, the same would go for her. If a woman or man who is asked out willingly offers to split the tab, then by all means the other halif if he/she so chooses should accept the offer.

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RE the older man with the young friend who has his wife worried. My brother in law, a college professor, had the perfect solution when this sort of situation happened. First he told his wife about the girl, then every time she showed up at his office he would call his wife who would show up and accompany them for coffee, drives or just office visits. The girls quit showing up in short order.

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Right you are Julia! I can see why he rarely has a second date. Why should we share our intelligence, wit and charm if he is not going to reciprocate in kind?