Ask Anna: I’m nervous about receiving oral sex
I'm 18. I've been seeing my boyfriend for four months. I go down on him, but he hasn't gone down on me because I'm nervous about it. What if he...
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I have a crush on my sister’s boyfriend
My sister has been dating a guy for about six months. He's great, attractive, caring, opens doors for people and is an all-around respectful person. I get along with him,...
I’m a delivery worker. Can I ask out a client?
I'm a straight guy in my 20s. I work for a delivery company and come across plenty of very attractive women as I go about my job. I have my...
The women you’re approaching don’t have problems–YOU do
I got some basic approach problems. I'm a white guy, and somewhat Hispanic-looking, in my 20s. I've lived all over Chicago, from the North Side, South Side and West Side....
On anal, role playing for beginners and valuing your own pleasure
Hello! I have a man I love very much. We're having a few issues, however. They are: Half the time he comes really fast and the other half it takes...
He won’t delete his exes’ photos from Facebook, and I’m jealous
I'm in love with this guy who is boss. He's the first guy I've dated. We're still not in a relationship; we're in the dating stage. I'm confused because I...
All the questions you need to ask yourself before having a threesome
I'm [an older] female, and my boyfriend wants to do a MMW threeway. Should I? —Anon. Dear Anon., That really depends on what you left out. Namely, do YOU want...
Summer dating advice: Don’t turn down oral sex when it is offered
Happy summer, my little everything bagels. It's time for beer-on-the-patio having and frolicking as the bunnies do (bunny suit optional). This edition of quick and dirty advice is here to...
What do you call a dating partner when you’re in the awkward in-between dating phase?
Hi Anna! I read your column in the RedEye every week! I have never been one to go for online dating, I'm just not into it. However, my sister is...
Am I a jerk for breaking up with my boyfriend during a difficult time?
I want to break up with my boyfriend. I've wanted to for a while. It's not the decision I'm worried about—it's that he's got a lot of shitty stuff going...