Ask Amy

Ask Amy column

I’m marking my 10-year anniversary of writing the “Ask Amy” column by running some of my favorite questions from a decade of advice.

Q. Let me start by saying this is not a midlife crisis. I am a 40-year-old guy who has never dated anyone older than 25. I recently broke up with a 19-year-old after dating her for a month. She was the one who asked me out, but the pressure from her friends and family was too much.

She then started dating someone her own age. Even though she left for school a month ago, we talk on the phone almost every night, sometimes for hours. This girl got to me like no one else ever has. I know we were made for each other, though at different times! I can’t get her out of my head. I don’t know if I should just keep talking to her and stay close hoping she may still have feelings for me.

Not That Old


A. Thank you for declaring that you are not having a midlife crisis. I agree. You are having a dim-life crisis. Before I attempt to slap you silly with the phrase “What can you possibly be thinking?!” I realize I have some major baggage here. Many of us do. At least those of us with teenage daughters. (If you attempt to date mine, by the way, I’m coming after you. Or better yet, I’ll send her father.)

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Her parents must be worried about this, and I would think that as their contemporary, you would try to respect them, at least a little bit. Since she is a (barely) consenting adult, there isn’t much anyone can do legally to prevent you from seeing each other.

I do feel, however, that the decent and adult thing is for you to back off — way off — in order to allow her to have a halfway normal time at college. I realize that by the time she graduates, she may be too old for you, but since you’re “made for each other,” I assume you’ll be happy to wait in spite of the fact she might outgrow you. (2003)

Q. My guy just broke up with me, and I’m frantic. What’s the best way to get him back?

Broken Hearted

A. The only method I know for sure is to stop caring. Once you really stop caring, they have a way of coming back. By then, of course . . . you don’t care. (2003)


Q. I am 50 and dating again — whew! It’s fun, but who pays is so confusing. He’ll ask me for ideas about what we can do on dates, and I’m afraid to make suggestions for fear that he’ll think I see him only as a wallet. The reality is, he makes far more money than I do — I work part time — and I can’t afford much more than a movie every now and then. How do others reentering the dating scene handle this?


A. Very badly, mostly. A basic guideline is that whoever does the inviting should pay for the date, and if your guy is asking for suggestions, it’s a good idea to keep those suggestions modest. You can reciprocate with the occasional movie date, inexpensive visits to landmarks, museums, and galleries, and your homemade lasagna.

Although this “who pays for the date” issue is still fluid with your guy, I hope you’ll muster up the courage to say to him, “Whew, this is fun, but who pays is so confusing! How do you feel about it?” He may confess that he has the same questions you have. The beauty of a new relationship is that you get to make up new “rules” as you go. (2004)

Amy Dickinson can be reached at Follow her on Twitter @askingamy or “like” her on Facebook.