After four dates, he is ready to bail because she won't pay

Wayne and Wanda

Dear Wayne and Wanda,

Tomorrow night is my fourth date with a pretty interesting woman, but it's probably our last.

She hasn't paid or even offered to pay for a single thing and I'm annoyed. I didn't notice until the second date. We had a late dessert and coffee. The bill sat there for 20 minutes before I paid. I watched close on the third date, and it was like bills don't even exist to her.

This is ridiculous. And the kicker is she's a lawyer and definitely makes good money. It sucks because we have killer chemistry, but I'm turned off by her sense of entitlement and lack of paying.

This next date is a concert. I prepaid for the tickets, of course, so I can't back out. But after that I think we're done. This is a new situation and I'm not sure what to say. I guess I would be interested in seeing where our relationship would lead if this problem didn't exist, but I'm pretty ready to bail. Suggestions?

-- No Sugar Daddy

Wanda says,

Clearly this stinginess is a big turnoff for you -- and annoying too. But is it really a deal-breaker? Let's review: She's attractive, you're attracted to her, and she's employed (a lawyer no less!). These days, those are some serious points in the "pro" column. After three dates, if this is the only real "con" that's percolated, I'd count yourself lucky and focus on seeing if this is salvageable.

There could be a number of factors for why she's Visa adverse in your presence, but here's one: Yes, you're baffled that your female friend isn't offering to pay or contribute in part, because you know she makes good money. But maybe she hasn't offered because she makes good money.

Let me explain. When it comes to dating, it is not easy to be a woman today who has a substantial income. I'm not talking a basic living-wage salary. I'm speaking for the females who earn some serious I-don't-need-a-man and I-can-buy-new-shoes-whenever cash. When you're trying to get to know a guy and you aren't sure about how he feels about the fact that you almost surely make more than him, it's hard to know whether he will be wounded or offended if you offer to pay or even go Dutch.

This is especially true in Alaska, the land of the dominant uber-male, hunters and fisherman, and slopers who fancy themselves super-providers on all levels.

In an era when chivalry seems dead, sometimes antiquated but sweet gestures like letting men open your door or -- yes -- foot the bill seem like sweet, necessary concessions. So before you write this lady off as cheap and clueless, consider the fact that she may be more aware than you know, fumbling her way along in an attempt to please you.

Wayne says,

Look at Wanda Warbucks over there, stacking dollars and breaking hearts! Do your thing girl!

I'm guessing it's easy to get rich when someone else is picking up all the checks along the way. I certainly don't think this is what Beyonce and Destiny's Child envisioned when they dropped the insightful "Independent Ladies" on us.

Hey man, did you ever think that this isn't a test of your wallet -- maybe it's a test of your backbone? If so, you failed. I'm wondering why all of these games are necessary. Seriously. Why would anyone worth dating (independently wealthy or baller on a budget) put a love interest through four financial tryouts before making a long-term love investment? And why would someone worth investing in be so concerned about a great date with short arms and deep pockets?

Communication and finances are two of the main reasons that relationships go bankrupt. You haven't even embarked on a real relationship with this woman yet and you're already struggling in both areas.

It's time to think about why you're dating. If you're just out there just to date around and sleep around, then yeah, you've already put in way too much time and money for this thing to pay off. But if you're dating with the hopes of meeting someone to spend your life with -- you know, the reason most people date -- it sounds like you've found someone with some potential. A few meals and concert tickets on your debit card are a small investment for a possibly big payoff. Stop complaining and keep paying.

• Wanda is a wise woman who has loved, lusted and believes in retail therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at