While cleaning out boxes from my mother’s house, I found photos of an ex-girlfriend (we’d lived together four years). 

She’d left me; the breakup had destroyed me. She had no intention of marrying me or sharing my family (I had a child, 3).

Since seeing the pictures, I’ve been in a state of depression. I can’t stop thinking about her; our split happened 29 years ago but I remember it like it was yesterday.

I cry about her when I’m alone and it’s affecting my marriage.

I want to contact her but only have her sister’s address. I want to see her again… am I nuts?

I’m 59, married and was happy.

- In Love With The Wrong Person

You’re not “nuts” but you’re also not stable regarding this old, deep wound. 

And you’re certain to create huge turmoil if you proceed to pick it open again because the huge odds are that you’re caught up in a fantasy about redeeming yourself and wiping away what felt like a failure to you.

Meanwhile, you’ll devastate your wife - a cruel result of your trying to turn around the same thing having been done to you.

Then there’s the Old Flame herself – possibly so uninterested that you’ll be rejected again and thereby get more depressed.

OR - here’s the most unlikely but just as destructive scenario – she’s flattered by your contact, wants out of a crummy situation, and flies into your arms.

But you don’t know each other anymore and the relationship could be a total bust, yet cause upheaval to you, your family, and your finances.

I recommend you put those very old memories back in the box, throw away the photos. And, if you’re still crying, see a therapist.

I’ve been dating this man for 6 months - he has many good qualities, but he’s so messy!! I’d noticed immediately that his car looked like a “dumpster” full of garbage and old newspapers, fast food bags, etc. He apologized, but he’s still like that in everything he does. 

He’s a successful businessman, wealthy, smart yet his office is worse than his car.

I’ve tried to clean up and organize but he doesn’t like the idea, it always returns to a mess.

He also doesn’t take care of his teeth and always wears dirty gym shoes.

I’m thinking he suffers from some kind of a compulsive disorder because he cannot leave a restaurant without bringing a whole bunch of napkins, plastic stuff, whatever’s free.

I love him and don’t want to hurt him.

He’s hinted about living with me, but I don’t know if I can stand that. What can I do to help our relationship survive?

- Cleanliness Next To…

Simple solution: Insist that he spend some of his money on regular cleaning help (for the car, too), and to hire an office/home organizer to teach him some steps to quick clearing of clutter on a daily basis. Organizing experts can be found in many areas through the Internet. Make this a condition of your considering moving in with him. Do NOT make it your job. 

Complex approach: Insist he see a counsellor about his need to surround himself with clutter and also stockpile cheap items that can be available at any time. Again, make it a part of any deal to move in together. I say, “insist,” because this man’s habit is long entrenched and he’s unlikely to even address it unless he has strong motivation.

We’ve been dating for three months; we’re in our 30s, educated, with promising careers. 

However, he doesn’t open the car door or any door, doesn’t let me walk ahead first, and doesn’t help me put on my jacket.

When the bill comes he borrows money or asks me to pay half.

He wants me to pick up movie tickets, and make dinner reservations.

How do I suggest he change, if he’s serious about me?

He calls and emails everyday, we’ve met each other’s parents, and he’s planning a big trip for us.

- Looking for a Gentleman

You: “If we’re to take this relationship further, I need you to learn the manners that would make me feel you treat me as special, and with consideration. These are important to me – such as opening my door, letting me walk in first, arranging some of our dates, etc. What special things would you like me to do for you?”