Q: A few months ago, I renewed a relationship with my high-school sweetheart after many years apart. So far, it's been incredible, except for one problem: This woman has not once opened her purse. I am not a cheap guy, but she expects me to pay for everything with no offer to help. For example, she drives over to my house with her gas tank's empty light on. We use her car, and I'm expected to buy gas. At dinner, she orders the most expensive items and wine on the menu. I got club box tickets to an Eagles game, and she complained about everything. What should I do?
Steve: Send her a bill.
Mia: Hate to break it to you, but she's playing you. Any girl who's really interested in you will offer to pay after the first few weeks of dating - and should even offer to pay on the first date (though accepting that offer is the easiest way to not have a second date).
Q: There is a woman I see from time to time on business as part of my job. Ordinarily, I'd say she is out of my league: gorgeous, smart, great personality. But she seems genuinely interested in me when we talk, and I've been thinking about asking her out. She doesn't wear a wedding or engagement ring and has never mentioned a boyfriend. My hesitancy is that if I ask her out and she says no, will that ruin our business relationship? Is it worth the risk?
Steve: There's likely a way you can ask her out without asking her out. That would lower the risk of awkwardness that could affect your business relationship. Begin talking about family and friends and gradually note your availability. If she's truly interested in you, I suspect she'll drop a hint.
Mia: Ask her out casually for drinks or lunch first, then use that "unofficial" date to feel out whether she has a boyfriend or is interested in you. If she offers to pay half the bill, she's into you (see above).