Dear Harlan,

I’m not one to jump into bed with someone I just met. Well, the other night, I met a guy and slept with him the same night. We’ve gotten together a couple more times and I really like him. I know you tell people to make it easy without being easy. Is there hope? I’m sorry I was easy.

Not Usually Easy

Dear Not Usually Easy,

I accept your apology. Now apologize to the guy. Look him in the eyes and have a conversation. Not via text, phone or email. Do it face to face. Keep your clothes on and make it simple. Find out if he likes you or just likes having sex with you. Tell him that you’re afraid you misled him. Make it clear that you like him and want to continue getting to know him better, but sex is something you typically save for people you are dating. Make it clear that the sex was amazing, and you would like it to happen again, but you want to know what sex means to him. Give him permission to say whatever he feels. If he wants to date you — great. If not, don’t hate him. Respect him for having the courage to tell you the truth. Since you never required him to get emotionally naked before getting physically naked (and he didn’t either), you both did nothing wrong. Either way, ask him if he’s been tested for sex souvenirs so you need not worry about lingering memories from this one-night stand.

Dear Harlan,

I’m newly single and back on the market. I’m really kinky, and I like bondage, humiliation, etc. I’m terrified that because of this that I’ll never find a good man who treats me with respect and does that sexual piece for me too. Or they’ll think I’m weird. How do I bring it up to nice guys without scaring them away?


Dear Kinky,

Good men like kink. But it helps to know that the good man calling you names, spanking you and humiliating you respects and cares about you. Before whipping out the whips, handcuffs and leather, start the relationship by establishing a foundation of respect. This will take some time. You need to know that the man you’re dating respects your boundaries and likes spending time with you. Once you know a man doesn’t have any outstanding warrants, has a life outside of you and treats you the way you deserve to be treated (during daylight hours while sober), bring up your bedroom kinks. Start with a conversation at lunch or dinner. Bring up one or two small kinks. Introduce him to something more familiar and less extreme. Ask him what he’s into. See how he responds. He might be open to learning. You can even start out an intimate relationship without bringing up the kinks. Don’t make this a terrible kinky secret, make it one small part of you. The better you know a man, the more comfortable it will be to open up. The more he enjoys spending time with you, the more open he’ll be to new experiences. And as a rule, it’s safest to talk about sex while fully clothed outside the bedroom. Naked and surprised can be a dangerous combo.

Write Harlan at [email protected] or visit online: Send paper to Help Me, Harlan!, 3501 N. Southport Ave., Suite 226, Chicago, IL 60657.

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