Awkward turtle needs to break out of shell

Hey there, time traveller!
This article was published 05/10/2018 (2915 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: I’ve never been in a relationship before, and I’ve had my eye on a guy I used to work with. Simple, right? I should just send him a text or call and ask him out for coffee. Au contraire!

This situation is a little tricky.

Problem 1: I am very shy and awkward, especially with people I don’t know very well.

Problem 2: He used to be my boss (I didn’t want to stir the pot while we worked together).

Problem 3: I haven’t seen or talked to him in more than a year.

Problem 4: He has since moved to a town that is a two-hour drive away.

Should I try to go after him, or look for someone else? I keep thinking about him, but how would I invite him out if he lives two hours away? I’ve never asked someone out on a date before, and I have no idea if he has a girlfriend. We haven’t kept in touch. Is it too late?

— Awkward Turtle, St. Vital

Dear Turtle: If he’s single and free — you must casually ask him right away — there’s a chance he’s lonely in his new town, and might really enjoy connecting with you. So start getting active.

Come out of your shell far enough to contact him on Facebook. Post stuff you know he will like and comment on it in a private message to him. Use any excuse to get him on the phone and add a warmer dimension to your interactions.

After a few weeks, find a fun event attend near him and ask him to meet you there. If he’s not willing to make the effort, he’s definitely not interested in you.

If you just tell him to call you when he’s in Winnipeg, it could be a long wait. And you still wouldn’t know if he liked you romantically or if he was just catching up with an old friend from work.

Dear Miss Lonelyhearts: I’m lacking in male friends because I’m good-looking, and women like me. I’m also outspoken on business, religion and politics.

My sister told me to “tone it down’ if I want more male friends, but I can’t seem to do that.

Women are just fine with me the way I am, but men get competitive very quickly, and I don’t back down. I would like to have some buddies, but I don’t want to change.

— Mr. Competitive, Tuxedo

Dear Competitive: You need tougher buddies so you can pick on people of your own size and intelligence.

Choosing friends from a pool of more aggressive, athletic guys in a team or a sport like weightlifting might work.

The gentler, soft-spoken guys are not a good fit for you.

Trying to be buddies with guys who are softer than you will only lead to competitiveness or avoidance on their part.

Choose men who are just as outgoing, combative and good-looking. They won’t need to compete with you to prove anything.

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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