Dear Harlan,

I got out of a bad relationship a year ago. Since then, I’ve moved on from him and am ready to get back into the “scene.” I’m a single parent of two, and living at home because I’m returning to school and my mother’s health issues. I know first dates consist of these questions. How should I approach these questions without scaring new potentials off?

Back in the Scene

Dear Back in the Scene,

Scaring them off? You’re a hot mom and you need to know it. Caring for your sick mom makes you kind and considerate. Not being married means you’re single and unattached. Going back to college makes you strong and driven. Having kids means you come with a family. Some men will run from this. Some men will stick around. Some men will want to hook up with you and decide later. Some will want to marry you. Don’t discount your attractiveness. You can be a woman in demand. As for what to divulge on a first date, slowly share what matters to you, but only as it comes up (sharing everything on the first date would be too much). Focus on getting to know your date and finding out if you like him. The better you know him, the more comfortable you’ll be sharing. As a rule, make it a habit to bare the truth before baring your body.

Dear Harlan,

I’ve been friends with this guy since I was born. Literally. Our moms were roommates in the hospital when they were pregnant with us. We lost touch for a long time after my family moved, but in college we’ve reconnected on Facebook. He’s the first guy that I’ve ever been really attracted to and shared some personal stories with. Likewise, he relies on me for advice when he’s going through a tough time, because he says he values my perspective. I think he may have tried to indirectly ask me out once, but I didn’t bite because I was too scared. Now I want to tell him that I really like him and have been wanting to date him for years, but he’s always got a girlfriend and I don’t want to make waves. I’m trying to accept that there are many other single guys out there who’ll want me, but no matter what I do I can’t get this one guy out of my head. I feel like if I don’t tell him how I feel, I’ll always wonder about it. What should I do?

Wondering

Dear Wondering,

You’ve got to tell him. Absolutely. But first, you’ve got to answer these three questions: (1) Do you have more than one friend? If he’s your only friend, you need to find more friends before telling him how you feel or you’ll be friendless. (2) Do you give him permission to not share your feelings? If you don’t give him permission to not want you, you’ll hate or hide from him if he doesn’t give you what you want. Not fair. (3) Do you have other options? That is, are there other men you can date? If you don’t think you have other options, you’ll never give him permission to not give you what you want.

Once you can answer yes to all these questions, you’ll be ready to ask him out and share your feelings. If he’s dating someone, let him know that if he’s ever single in the future, you’ll be there to offer a shoulder to cry on and lips to kiss.

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: www.helpmeharlan.com. All letters submitted become property of the author. Send paper to Help Me, Harlan!, 3501 N. Southport Ave., Suite 226, Chicago, IL 60657.