Dear Amy: I have been dating a 26-year-old a little over a year now.
I am in school far away, and we usually see each other only one weekend a month, but we get along great. My problem has to do with his last girlfriend, who was very beautiful and he dated about 1 1/2 years. (She broke up with him and is with someone else now.)
He likes to take me places occasionally on our weekends together. We have been to Charleston, New York and Atlanta, and now are planning a weekend in the Caribbean.
I recently discovered that he and his ex went to all these places too. I also found some photos of them trying on funny hats in a shop. We did the same thing, but I thought it was just spontaneous fun on his part.
Is this creepy, or should I not worry and just enjoy him? I think I love him, and I just hope he is not trying to relive his life with her. I know he was badly hurt when she left.
— H
Dear H: The next time you’re together, rent the movie “Annie Hall.” There is an extended sequence where Woody Allen basically tries to re-create a spontaneous and joyful time with a series of girls as a way of recapturing an experience. It is a childish yet understandable way to behave.
Your boyfriend might have “test driven” every relationship experience in his life. The only way to counter this is to get in the driver’s seat and do some of the planning and take some responsibility for your weekends. It’s time to go somewhere together where neither of you has ever been. Since you’ve been dating him for more than a year now and presumably know him quite well, it’s time to buck up and be honest with him.
I don’t know if I think this re-creation-impulse is creepy, but it certainly reveals a lack of imagination, and if it makes you uncomfortable, you should tell him so.
Dear Amy: I have a friend whose mother is dying of cancer. I wanted to ask you what is the proper etiquette in sending a sympathy card. What I would like to know is, how long should a person wait until a card is sent?
I know waiting longer than a week is probably not correct, but do you wait a few days after the death or do you send the card out as soon as possible? I really feel sad for my friend, and I just wanted to know the proper way to go about sending her a sympathy card to show her how much I care about her and her loss.
— Russ
Dear Russ: The proper thing to do is to send a note or card as soon as you hear about a death. But let’s throw out propriety for a minute. Your friend could probably use some support right now. I think if you sent her a note or phoned her to say you’re thinking about her and hope she’s OK, she would appreciate it.
Dear Amy: I’m 39 and recently started seeing an old college girlfriend (neither of us ever married or had children). Seventeen years ago when we were together, I was a few days away from asking her to marry me when she broke things off.
At that point I didn’t ask because it wouldn’t have been appropriate, i.e. it would have looked like I was being desperate and saying anything to keep her.
Now I’m about to propose again and am wondering whether to come clean about that past incident. Part of me doesn’t see any point in telling her. Who really wants to find out two decades later about a missed opportunity for marriage, children, etc.? On the other hand, part of me wants to be honest up front.
I’d hate for her to find out some other way like stumbling across an old diary or a friend or family member blabbing about what could have been.
— To Tell or not To Tell
Dear Tell: I don’t quite see why telling her the truth would be such a difficult thing. In my mind, your pre-empted proposal all those years ago isn’t evidence of a missed opportunity but one of those little relationship miracles that many people dream about.
You aren’t the people you were 17 years ago, and isn’t that a good thing? You can’t know what would have happened if you had proposed all those years ago — even if she had accepted. (I dare say there is some probability that you would no longer be together.) Your future now is as full of possibility as it ever was but enhanced by your life experiences, and I hope you can celebrate that.
I think a great way to march into your future together is to be honest about your past. If you do so in a way that is heartfelt and romantic (“This proposal was 17 years in the making . . . .”), she’ll probably find it is as charming as I do.
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Ask Amy appears Mondays through Fridays in Tempo, Saturdays in the Weekend section and Sundays in Q. Readers may send questions via e-mail to askamy@tribune.com or by mail to Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, IL 60611. Previous Ask Amy columns are available at Amy Dickinson’s Web site, Chicagotribune.com/amy.
