Dr. Date,
My boyfriend wants to try anal sex, but I don’t know how I feel about it. I’m nervous, quite honestly.
Tips? Tricks? Suggestions? I’ve really only heard horror stories.
—Anonymous
 
Anonymous,
Dr. Date,
I’ve been hanging out with this guy for a few weeks now, and it’s been really good. We have a good connection (we’re both really easy going and down-to-earth), and it’s progressed to the point where we’re ready to deem the relationship “official.”
But I’m having second thoughts.
Dr. Date,
Hey, I have a crush on my roommate, and I don’t know how to handle the situation. I knew I liked him before I signed our lease, and I thought that our time together would bring him around to the same feelings.
But he hasn’t shown any interest at all. In fact, since we moved in, we hang/talk less because we’re on completely different schedules. We were never really close friends before, but it seems like we’re strictly roommates now.
Dr. Date,
This isn’t a sappy, blah-blah-blah emotional question; it’s simple. Long story short, my ex-girlfriend and I got a cat together and now we’re broken up. The cat sucks. What the [expletive] do I do with this [expletive] cat?
—Pussy Problems
 
You Cat to be Kitten Me,
Man, get rid of it.
Dr. Date,
I want to start a relationship, but, honestly, I don’t have the slightest clue how. My flirting skills are nonexistent, and I don’t know how to show someone I’m interested. My biggest fear is rejection, and I don’t have any confidence in my attractiveness. I’m very average looking.
Dr. Date,
It hurt when my girlfriend told me, “I don’t have feelings for you like I used to,” but I learned to appreciate her honesty. It’s been three months since our breakup, and she’s currently dating a new guy who seems to be making her extremely happy.
Dr. Date,
I moved in with my best friend last fall, and it’s been great. We share a nice place, and because we have similar interests and priorities, there haven’t been any roommate problems. We get along well and our quality of life is through the roof.
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