Ask Helen: Handwritten note nice way to ease back into dating world

Dear Helen:
I met someone I like at a dinner party of a mutual friend. I’m mid-50s, employed, a decent-looking nice guy with varied interests. But I’m not yet divorced, and I am 15 years older than she is, though our mutual friend says that shouldn’t be a problem. She told me Sarah is recently divorced and not yet ready for a steady. Should I risk getting shot down and ask her out? How can I let her know I’m interested without putting her on the spot? I’d like her to say yes, but if she says no, I still want invitations to the friend’s house. It’s been 30 years since I’ve dated, so I’m kinda rusty.
Would-Be Suitor

Dear suitor:
Few things inflate one’s ego more quickly than knowing someone is interested. That’s especially true if the would-be suitor is decent looking, employed and nice. But it’s equally true that turning someone down can be awkward and stressful.

Ask your mutual friend for Sarah’s address. Then send a friendly note that says roughly, I enjoyed meeting you. I’d like to connect again one on one for an activity you think might be interesting to do together. My range includes going out for food, a movie, going for a hike or a concert, or taking dance lessons. Here’s my contact info. Please let me know if any of this sounds like fun. By giving her time to think about if and how she’d like to begin knowing you better, you’ll demonstrate your nice-guy-ness. By including dance lessons in the range, you’re demonstrating interest in something more intimate than a hike, but not in a sleazy way. A handwritten note is more personal, but email is more modern and faster, assuming you don’t land in her spam bin.

One cautionary P.S. – Don’t say anything you wouldn’t want your mutual friend to read. Your notes and any possible future romance is very likely going to be shared by the gal pals.

Dear Helen:
I just moved my winter clothes to the back of the closet and got out my spring and summer duds. I cried after I tried on my favorites from last year. I don’t want to buy a larger size but going naked is not an option. I need to lose 20-30 pounds. Note: That same sentence with 10-20 has been true of my life and body for almost as many years as pounds. I’m what we used to call politely “zaftig,” which in my fractured Yiddish memory banks means something like juicy. I don’t expect to ever be skinny again. But I would like to be a size smaller, to wear the nice clothes I already own and to be able to walk in a 5-mile race this summer with my friends.

Dear Help:
You’re describing a long-run problem, so don’t embrace the false promises of a mythical short-run solution. Many diets promise lots of quick weight loss, but there’s only one healthy way to take and keep it off: Eat less. Move more. Start with those and you’ll be your slimmer self again soon enough. My mother would always tell me, “I’ll pay for Weight Watchers.” I wish she were around now so I could say “Thanks.” You don’t have to join a specific organization, follow a specific food program or even join a gym. But studies show that tracking what you eat will help you make better choices. Ditto moving and sweating.

Find a buddy who is sincere about teaming up with you. Not just a kvetch-and-do-nothing buddy, but someone with similar needs and goals, preferably motivated to exercise with you or connect regularly on progress. Ask if your health plan offers weight-loss coaching. Find a few outfits to tide you over for a month or two. Even a few pounds lost will help your old clothes to fit. Set reasonable goals, and see how achieving them inspires you to make real and lasting progress. Reward yourself with things other than food.

A resident of Eugene since 1981, Helen is a member of Temple Beth Israel, where she studies and speaks on Torah. She claims to have black belts in schmoozing, problem solving and chutzpah. She’s a writer and an artist ( Please email your questions to and subscribe to the blog at

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