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Start making passes at guy in the glasses

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Dear Miss Lonelyhearts: I'm falling for a guy in my class. On the first day in September he was staring at me. A few classes later we were sitting together, chatting and inseparable. Now we discuss really personal things and stare at each other smiling. I want to reach for his hand badly, but I worry he might just want a female friend. He did tell me he was afraid to ask a woman out. My friend said that was a cue to ask him out. I miss him a lot when he gets depressed and takes time off. During our last class it was on the tip of my tongue to ask him out for coffee, but I couldn't. Instead, I told him he was good looking and he beamed. I was so disappointed in myself I went home and threw up. He is so attractive with cropped dark hair and beautiful eyes behind glasses. It didn't seem to faze him that I'm a mom. I dress up to see him, have lost weight and lightened my hair. So how do I get the nerve to ask him out? -- Smitten, Winnipeg


Dear Smitten: You've been sitting in class for over six months staring at each other and talking about intimate stuff, so it wouldn't be creepy to write him a cute note asking him out. Then ask: "Well, yes or no?" If he can't squeak anything out, lean in and kiss him. You need to take a chance, however small! You could hint shamelessly by saying, "If you ever asked me out, I'd say yes, you know." Then take off for your next class and let him digest that piece of news. The next day, say: "If we went out on a date, where would you like to go?" He should be getting the general idea. If he looks uncomfortable, but happy, say, "How about the movies this weekend? Which one would you like to see?"

Yes, you're taking a chance he might say, "Sorry, I just want to be friends," or "Don't you know I'm gay?" but it's not likely if he's always staring at you. That's a sign of physical attraction. As for his depression problem, you should fish around and see how serious it is. Maybe that's what stops him from forming a deep romantic relationship.


Dear Miss Lonelyhearts: I'm sad because my girlfriend from university, whom I had a relationship with many years ago, has gotten married to a guy. He's a very nice man who doesn't know about us. I was invited to the social where she got a little drunk and I told her how beautiful she looked. She replied: "I loved you so much, and still do, but I wanted kids and a real family." Real! I couldn't believe I heard her right. This was seven years later and she still obviously has feelings for me. I am now guessing she must have made that decision way back then, or did she dump me for other reasons? She disappeared with no explanation.

I haven't slept well since I started thinking about her and what it might have been like to marry her. Lesbian couples get married and have children, too. Maybe she wanted the kind of family that looks "normal" to everyone. I also feel pretty angry. If she loved me that much, why didn't she tell me then? Why did she disappear? Should I ask her? It's tearing me up! -- Heart Churning, Fort Rouge


Dear Heart Churning: Ask her! You will spend a lifetime wondering if you don't find out now. She opened the discussion with her drunken confession, so she can at least go for coffee with you and answer a few questions. Make a list of up to five major questions you want to ask so you only have to do this once to clear up the mystery. If you're afraid you'll forget one, write the list on a tiny piece of paper and slip into the bathroom and re-read it if you need to. You're doing this for truth and healing, so do it right.

Republished from the Winnipeg Free Press print edition February 20, 2014 C2

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