Does he have to pay for dates?

I feel as though I am in a no-win situation. I am a single 30-year-old guy, and I recently moved to Boston for a job. I knew a few people here, so it was not like I came here and was alone. I have been dating around since I moved here, and while I love dating and meeting new people, I always wind up paying on a first date. It has gotten to the point that it is absurd. I have spent upwards of $90 on drinks and dinner. Most of the time, I don't hear back from the woman. That is not what bothers me; I get it, dating is a numbers game. However, am I too old-fashioned? Even when a woman offers to split the tab, I decline. Should I start accepting their offers so I don't go broke dating? When a woman does offer, is this a polite way of saying she is not interested?

– Old-fashioned

Some women offer to pay when they're not interested. Others offer to pay because they want to be fair. I remember one woman telling me that if a guy let her pay, she assumed that he wasn't interested. Basically, everyone is confused and making up their own weird rules.

Your best bet is to start with coffee. Coffee first dates are great because they're all about conversation, and talk is cheap. Even if you go to the fanciest cafe, the bill shouldn't be over $20. You can reserve dinner and drinks for date two or three.

Also, if someone offers to pay more than once, it usually means they want to split the check. That means you should let them. You can just be honest and say, "I never know what to do at this point. Thank you for splitting the check, but I'd like to treat you next time."

Readers? Coffee? Do you use the check to indicate whether there will be a second date? Is this problem reserved for men dating women?

– Meredith