He’s 29 years old, never kissed a girl

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This article was published 02/10/2018 (2925 days ago), so information in it may no longer be current.

Dear Miss Lonelyhearts: I’m a 29-year-old man who has never been on a date and never kissed anyone. I’ve been attracted to women, but fear and anxiety have held me back. Also, no one has ever shown any romantic interest in me.

I really don’t know how to go on a date or what to do afterwards. I’m also very quiet, not very conversational and I don’t like bars or any other loud/crowded places. Now that I’m almost 30, I’m embarrassed to tell anyone that I have no experience whatsoever. How should I approach this conundrum? A life/dating coach perhaps?

— Embarrassed Shy Guy, Winnipeg

Dear Embarrassed: First thing you need to do is work out the problems that are holding you back. Address the shyness problem — the root of your social angst — with a psychologist. At the same time, address your physical confidence part with exercise, perhaps weight training. Got a weight problem? See a dietitian who can design a meal plan specifically for you. Haircut behind the times? Ask people with great dos who they recommend. Are your eyeglasses boring and old-fashioned? Find a saleswoman to help you pick out frames that are appealing to women. Clothes not doing anything for you? Check out magazines to see what men are wearing. Not much of a wit? Read clever or funny books and develop your own sense of humour.

With a better look and more self-confidence, start checking out meetups.com for activities in Winnipeg, where you can meet other people with the same interests. You don’t just have to go to singles events. Follow your true interests and “tune up” your personality. As you become more interesting, it will be much easier to talk to women who like your type of guy.

Dear Miss Lonelyhearts: Every year about this time I start thinking about Christmas, and it makes my heart pound and my palms sweat. My mother died 27 years ago just before Christmas, and she hoped I would keep our small family together. We have two grown children and one grandchild. My husband and I each have a sibling with families, and we each have a parent still alive, but just barely. I’ve always been the one making the Christmas, Easter and birthday dinners, so that the family would be together and keep in touch. My husband’s family and mine never did like each other very much. Most of them would literally eat, drink, burp and then leave.

For the past five years, I’ve only put on Christmas for my children. It has been much easier, but my mother’s wish is still ringing in my ears. Now, it could be because my mother-in-law may not live much past Christmas, or because my daughter has very little family, but I have told my husband that since we will not be in this house next year, I would be willing to have his family over for one last get-together.

He looked at me as if I was crazy. Should I do this? Is my dream of getting this distant family together one more time a little too ambitious, or should I just leave well enough alone?

— Christmas Problem, Winnipeg

Dear Christmas Problem: Your mom, now gone these past 27 years, isn’t around to know or care. But if you want to do it, invite the whole family and request that they RSVP early. Then, see what number you have and enlist your daughter to help with the cooking a couple days ahead of time. Make it fun and cook together, with Christmas music and TV shows in the background. If not many people are coming on Christmas Day, invite some fun neighbours who might be having small parties or have nothing much to do. Or consider hiring a live musician; it’s fun and takes the pressure off. Make Christmas 2018 a good time, not a hard time, for you.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave. Winnipeg, MB, R2X 3B6.

Miss Lonelyhearts
Advice Columnist

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