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I'm a shy thirtysomething who's never dated - now I have a crush Add to ...

Group Therapy is a relationship advice column that asks readers to contribute their wisdom.

A reader writes: I’m a shy guy in my early 30s who has actually never dated. I’ve had crushes but never the courage to tell girls I like them. Last summer I travelled to Europe for a Catholic gathering and fell for a girl who is 21. I’ve seen her twice since then but have said nothing about my feelings. How do I let her know I’d like to get to know her and see what happens? I’m worried she may be more experienced than me in relationships.

Start small

As a guy who never dated until my late 20s, I'd say, “What are you waiting for?” I always assumed that my crushes were too good for me and I made the excuses so that I never had to hear NO. Don’t build it up bigger than it is. Start small with a meal and don’t be afraid to ask at the end of the night if it’s something she'd like to do again. Every relationship is new at the beginning and experience doesn’t dictate if it works or not.

Todd Simpson, Windsor, Ont.

Try being friends

When my husband and I met, he was the shy guy. He had never had a girlfriend, while I’d had other boyfriends. We met in college and got to know each other, talking a lot about our pasts. He was never judgmental. We started dating and a year later we were married! So do not be afraid to ask her out as a friend at first. Hang out, get to know her and do not think about her past. Be honest with her and yourself. The worst outcome is that you may have a new friend.

Lucia De Santis, Brampton, Ont.

Chalk up some experience

Not to put too fine a point on it, but with each passing year, the women you meet and are attracted to are going to be more and more likely to have more experience than you. That may matter in the case of this girl in particular, but it really may not. Attraction is one of those funny things that can break down almost any barrier. That being said, if she does not return your affections, don’t get discouraged! Even rejection is a form of experience in love.

Adam Green, Ottawa

The final word

My mother comes from the world of arranged marriages. Nobody, no matter how shy or bucktoothed, got left behind. When I put my foot down and refused to partake in what I thought was a medieval custom, I found out fast that there is one significant benefit to meeting your spouse on your wedding day: no work.

And work you must do in order to meet your future partner. The woman you’re interested in belongs to the Facebook generation, so do your homework. If you find out she’s in a relationship, it’s not the end of the world because, last I heard, there are still single women left on this planet.

And if she’s available, take Todd’s advice. Start small. Ask if she’d like to meet for coffee and see what happens. If that’s too difficult, it’s time to bring in the cavalry. Asking people who care about you for introductions is another way to meet people. I was nerdy, weird and simply incapable of attracting someone on my own. When your conservative Muslim mother tells you “it wouldn’t kill you to flirt with a man,” you know you’ve hit rock bottom. My brother actually had to phone his friends across Canada in a hunt for a suitable husband. After exhausting several provinces, he struck gold in Saskatchewan.

Dating websites are a fantastic resource. I would go to one that says something like (I’m just guessing here) “www.womenin10mileradius.com” and be honest in your profile. Share, among your other good qualities, that you’re shy and don’t have a lot of experience. Like Lucia said, the right woman won’t care. And if you don’t judge her, she won’t judge you.

Remember Adam’s advice: Rejection is par for the course. You can’t let it deter you. It’s either that or have my mother hook you up on your wedding day.

Regina-based Zarqa Nawaz is the creator of the CBC-TV sitcom Little Mosque on the Prairie.

Next week’s question

My best friend began to date my husband’s brother. Now we’re sisters-in-law, and I’ve pretty much had it with her constant dramas. Although I’ve tried to withdraw, she continues to demand my attention and advice. I still have to invite them to dinner, and help them out when needed, because they’re family. But how do I keep a lid on her obsession with airing every grievance, especially when it gets our husbands riled up?

Let’s hear from you

If you would like to participate, e-mail us at grouptherapy@globeandmail.com. All questions are published anonymously, but we will include your name and hometown if we use your response (it will be edited).

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