Dear Kate, The first person I loved broke my heart. Now we are friends, but he keeps telling me the details of his various flings. How can I tell him that these stories make me uncomfortable, but still keep our friendship as close and open as it is now? -Hiding a broken heartDear Hiding, It doesn’t sound to me like your friendship is actually as close and open as you’d like it to be. Invite your friend to sit down with you for a cup of tea, and then let him know that stories of his new adventures in dating are not the type of tales you’d prefer to keep hearing from him. Inform him that constantly chronicling his recent trysts is making you upset. He may not even realize that his comments are hurting you, and telling him how you feel will likely cause him to be more sensitive in the future. Before you chat with him, have a list ready in your mind of topics you’d rather discuss. For example: Ashlee Simpson: Does she really deserve to be famous? Or, “How much would you pay me if I ate this wad of gum stuck underneath the table?”
Dear Kate, I have a date coming up with a woman who I really respect and admire for her intelligence and charm. I’m not sure whether or not I should pay when we go out, seeing that I don’t want her to think that I’m cheap, but I’m afraid she may think I’m being condescending if I insist to pick up the tab. What should I do? -Not Cheap, Just Checking
Dear Not, First of all, I don’t think I ever agreed to go out on a date with you. But anyhow, in response to your inquiry: I think it’s fair that each person pay for their own meal. Aside from considering the tradition of the guy paying for each date to be old-fashioned and outdated, keep in mind that we are still college students, and until the payroll department decides that we ought to earn some decent wages for on-campus jobs, we’ll still be pinching pennies. Your date should expect to have a good time, but still be willing to pay for it. Show this woman that you respect her by doing little things: keep eye contact when she’s speaking to you, hold the door, and mention that you enjoy her company.