CheekyChicago

Q: If you go home with a guy and pass out and he gets frustrated because you won’t hook up with him, but you really had a good connection, should you go out with him again?

A: Right or wrong, when you go home with a guy, most guys will assume something sexual is going to happen.  I don’t know what his outburst looked like, but clearly it’s because he had an expectation that something would happen, and was disappointed that it didn’t.  If you like the guy it’s absolutely okay to go out with him again, just be more up front with what you’re comfortable with and how you want things to progress.  Understand that he might not want to go out again, but if he decides he does, he can’t be disappointed.

Q: My 24-year-old brother is about to move to the city from the suburbs.  He’s single and a former college football player so he’s bound to get into trouble.  Do you have any advice for him?

A: If he’s a former football player, he already knows the importance of always wearing protection.  The only other thing I can offer is what my parents told me growing up: “Don’t do anything you wouldn’t want to read about on the front page of the newspaper.”

Q: My boyfriend won’t phase out of his polo shirt/tan cargo short phase, not to mention his backwards Wisconsin Badgers hat.  The look is fine for a 21-year-old.  He needs to grow out of his college days and into a working professional.  What are your favorite outfits to go from working during the day, to meeting friends for dinner at night?

A: I work in a job that allows me to wear “going out” clothes all day, so I’m not the best example.  Rather than worry about what I like, if I were you, I’d get him dressing in what you like.  You’re the one that has to look at him.

Q: Considering you work at a restaurant, what could a girl cook to impress you on a date?

A: The first thing I would do is find out if there is anything the guy hates or is allergic to.  Then I’d make whatever you consider your best dish.  Whether it’s a great veggie lasagna or killer turkey chili, the goal is making something you love for him, not being his personal chef for the day.

Q: I have noticed that once I have known a guy for a considerable amount of time, there is a week’s period every month that his mood swings almost as much as any girls’ during her period…have you noticed at all that guys tend to PMS once a month as well?

A: I spoke to a friend of mine who is a doctor.  Medically and hormonally speaking, he said guys’ hormone levels stay pretty consistent throughout their life, not fluctuating on a monthly basis like women.  He suggested looking at other factors that might be affecting his mood over the course of a month.  Maybe bills stress him out at the end of every month.  The bottom line is, if there is a noticeable shift in his mood on a regular basis, do some digging to find out what’s really causing it.