Dear Annie: I am 75. I’ve been single for more than 20 years. I was resigned to live my life as a single woman. However, a man I dated 57 years ago called me out of the blue last year. He told me he’d outlived his wife, “Sheryl.” They were married 22 years; the ex passed away 10 years ago. He invited me to visit him, and I did, twice. We felt a great connection. He is very kind, caring, and respects me.

My problem is that I’m jealous of the deceased wife. When he brings up her name it rubs me wrong. I find I compare myself to her, and any other woman he knows, even ones who are only friends. I constantly wonder if I can measure up. I hate this about myself. Can this be remedied? — Envious of Everyone

Dear Envious: First, recognize that his late wife is not an “ex.” She will forever occupy a huge place in his heart. That doesn’t mean there’s any less room for you.

In time, as your relationship to him deepens, you will feel more trusting of him and naturally less threatened by his female friends. You may even become close with them.

You haven’t dated in decades, so it’s perfectly natural to have some insecurity and uncertainty about how to conduct yourself in a relationship. Continue depriving this unfounded jealousy of air, and you’ll gradually snuff it out.

And keep in mind that this man reached out to you, 57 years later. You must have made quite an impression.

Dear Annie: I wanted to say a few words to “Black Sheep,” whose mother was keeping him or her from going to the college of their choosing.

My mother didn’t want me to go to college either. The best things I ever did in life was A) Go to college and B) Take advantage of the free/low-cost student counseling once I was there. It turns out that our predicament wasn’t unique to our families and there are experts who can walk you through the emotions that come with striking out on your own under such stressful circumstances. Do both. Chase your dreams and find a professional to talk to about it. I’m 38 now, and I’m living a life and thriving in a career I never could have dreamed of, and it was only possible because as the black sheep in my family I found the courage to chase my dreams. You’ll never regret it if you do. — Black Sheep Made Good

Dear Black Sheep Made Good: I’m glad to print these wise words from a black sheep who has found her flock.

Dear Annie: My husband and I could have written a similar letter as “Failure to Launch Father.” Our son dropped out of school at age 16. He started partying all night and sleeping all day. On his 18th birthday, he was given several options: 1) Go back to school full time; 2) go back to school part-time; or 3) get a part-time job to help contribute toward the household expenses; 4) get out.

He chose the fourth option. We were never sure where he went, although there were times when I could see him sleeping in the park across from my office (so sad).

Long story short, he moved to a nearby city, got a job as a bike messenger and worked as a roadie. He got his GED and went on to college. He graduated at the top of his class. He now works for a top tech company. It was a long road, but tough love does work. — Been There, Done That Mom

Dear Been There: I’m sure this letter will offer some encouragement to “Failure to Launch Father” and any other parents hesitant to dole out some overdue tough love. Thanks for writing.

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“Ask Me Anything: A Year of Advice From Dear Annie” is out now! Annie Lane’s debut book — featuring favorite columns on love, friendship, family and etiquette — is available as a paperback and e-book. Visit http://www.creatorspublishing.com for more information. Send your questions for Annie Lane to dearannie@creators.com.