You'll Never Regret it

By Cheryl Lavin

August 5, 2016 4 min read

Dear Cheryl: I've been living with my boyfriend for 11 years. We're both in our late 50s and we both have adult children. He and his ex-wife have not spoken in years.

She was recently diagnosed with cancer, and she has asked him to drive her to chemotherapy appointments. (By the way, she lives 50 miles from us.) She says she doesn't want to bother the kids, who live out of state. He's conflicted about it. I'm outraged. There are public services for that. I think she still has feelings for him. I guess I'm feeling threatened by this, but I still feel her request is inappropriate. How should I handle this? — It's Not Our Problem

Dear It's Not Our Problem: I think the request is a little strange, considering they haven't spoken in years. And I find it sad that she doesn't have any friends or family she can ask to take her. I understand both your feelings and your boyfriend's.

All that said, I think your boyfriend should offer to drive take to her one or two appointments and then help her find some other transportation. She probably reached out because she's feeling overwhelmed with her diagnosis. Encourage your boyfriend to be the bigger person and respond with kindness. And you should do the same. I don't think either of you will regret it.

Dear Cheryl: I'm 28 and I've never been married. I had a rough childhood, and it affects my adult life. I was raised by a single mother, and I have a sister who's two years older. My mother's idea of punishment was dressing me in girls' clothes and putting curlers in my hair and making me do the housework. My sister and her friends put makeup on me, painted my nails and tied ribbons in my hair. I left for the Navy 10 days after high school and haven't seen either of them since.

Some of this has carried over. I don't wear women's clothes or makeup, but I do enjoy having a woman comb my hair and put it in curlers. I've had two steady girlfriends, and it took me a long time to tell them. The first didn't enjoy it, but she would do it once in a while.

It took me a year to tell Barb, my second girlfriend. She said it wasn't a problem and really indulged me. She even gave me a perm and bought a shampoo chair at a garage sale. I can't tell you how many dinners I ate with a curly do and a barrette or ribbon in my hair.

She moved away to pursue a better job, but before she left she gave one of my co-workers a picture of me with curlers in my hair. Should I ever tell anyone else about this or keep my fetish to myself? — Former Navy Man

Dear Former Navy Man: Barb was unspeakably cruel. As far as fetishes go yours seems harmless. It doesn't hurt anyone, and it gives you pleasure. Continue doing what you've done. After you've really gotten to know a woman tell her that you'd like her to play with your hair. Tell her eventually you'd like her to set it, and so on. If she agrees, great. If she doesn't she's not for you.

Got a problem? Send it, along with your questions and rants to [email protected]. And check out my e-book, "Dear Cheryl: Advice from Tales from the Front."

Photo credit: Kurt Bauschardt

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