Dear Harlan,

I am in a bit of a dilemma. I’m single and have slowly been getting back into the dating game (my last real relationship was three years ago). I recently met a guy while going for a run one day, and he seems nice. We met up for a drink, and I felt pretty confident talking to him. Everything seemed to be going well, until he brought up his background, and it is a little bit “shady.” I appreciate his honesty, but I’m afraid that this has changed how I view him. He has told me he wants to get back on his feet and has made some effort, but I feel like I am judging him (and I know I shouldn’t). Is it right for me to judge a person on what I deem to be some serious issues (even if they are in the past) or should I try to get to know this person and understand before I draw more conclusions? I have a good idea of what I want in a partner, but I feel that maybe I’m overanalyzing this situation.

Confused in the Shade

Dear Confused,

Judge him. If you’re going to date him, it’s OK. Don’t convince yourself that any of this feels right if it feels wrong. Trust your gut. Let it be your compass. There are women who won’t mind his shady past. And there are too many men without a shady past to convince yourself that you should date him if you don’t feel right about him. Do not feel obligated. Do not feel bad. Look inside yourself and never look back.

Hi Harlan,


My father was a sex addict, so with that comes a lot of insecurity about my own sexuality. I wonder, “Am I going to be just like my dad?” I like sex (I’m a virgin and female but I think about it a lot, and I’ve tried masturbation). I’m anxious and I don’t want to do it for religious reasons and guilt. My friend wants me to start doing it because he thinks it might help me relax and de-stress. Also, I’m nervous about sex in general. My religion plays a big part in that, and I don’t want to have sex until I’m married, but I want the closeness (both physical and emotional). I’m conflicted. I want to listen to my friend and not feel guilty that I’m turning my back on my religion. I think about all the things that could go wrong. I’ve decided I need counseling to figure out what I want. Seeing as I’m not in a relationship, I think masturbation just reminds me of how lonely I am, and therefore I don’t want to do it. I’m conflicted and miserable. I don’t know what to do. I feel like I’m going crazy.

Spinning in Circles

Dear Spinning,

Thanks for the note. Know what you need? Someone to tell you: “It’s OK. This is all normal. I understand why you feel what you’re feeling. But your dad’s addiction is not yours. Religion is forgiving. We are all imperfect. Give yourself permission to be imperfect. Surround yourself with people you love and trust. Lean on them. Engage in self-discovery. Get to know your body. Demand respect. Develop your own relationship with God. Never forget that you are loved, supported and forgiven.” I’m glad you’re getting counseling. You need someone other than me to tell you all of this.

Harlan is author of “Getting Naked: Five Steps to Finding the Love of Your Life (While Fully Clothed and Totally Sober)” (St. Martin’s Press). Write Harlan at [email protected] or visit online: All letters submitted become property of the author. Send paper to Help Me, Harlan!, 3501 N. Southport Ave., Suite 226, Chicago, IL 60657.

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