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Amber Madison

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Latest Content by Amber Madison

What If My Girlfriend Sucks at Giving Oral Sex?
Q: My girlfriend gives terrible blow jobs. On a good day, they're just boring. On a bad day, she'll scratch me with her teeth. I like her...what can I do? A: The answer here is surprisingly Read More >
drunk hookup
How Do I Tell Her We Made a Drunken Mistake?
Q: After a night of drinking, I hooked up with a girl I know, and now I’m afraid she wants more. How do I let her down easily? A: First of all, don’t assume she wants more, just because Read More >
concerned couple by water
“How Do I Tell Her I Have an STD?"
Q: "I have an STD. When's the right time to bring it up with a new girl? A: Is it ideal to have an STD? No. But is it a deal breaker if you’re an all-around great guy? Of course not. Read More >
Couple talking on subway
Is There a Non-Creepy Way to Ask a Stranger Out?
Q: There’s a woman who rides my train every morning, and I’m really attracted to her. How do I break the ice without looking like a stalker? A: The only way you’d look like a Read More >

More by Amber Madison

bedroom pillow fight
Can I Ask My Girlfriend to Have a Threesome?
So this is the year to make your wildest sex fantasies come true, huh? Here’s what you need to know before welcoming someone else into the bedroom.
Q: “I’ve always been curious about what it would be like to have a threesome. Problem is, I’m involved with a great girl. Can threesomes ever be part of a healthy relationship?...
Read More >
man asking woman to forgive him
What’s the Best Way to Ask For a Second Chance?
You were busy, so you blew her off—is there any way to make amends? Maybe. Here’s how to handle it.
Q: “I met a girl at a busy time, and to be frank, she wasn’t a priority. But now I regret that I let her slip away. How should I go about getting back in touch?” A: If you want a...
Read More >

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