Dealing With Insecure Guys by Ask Rob! The Advice General

Ask Rob! The Advice General
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Dear Rob,
There is this guy that I really like that I see during the week, we work in the same building but not for the same company. When we run into each other we talk a little, but he doesn't say too much. I know he likes me because I see him stealing glances at me when he thinks that I don't know he's around, in the cafeteria, elevators, common areas of the building.

I flirt with him and he smiles then retreats. I've hinted that we should go out and he always says something like, "that sounds good", or "sounds like fun" but he never takes the hint.

From the small talk we've traded I know he's not married or dating. We only see each other at my work building. How can I get him to break out of his shell and ask me out?

Thanks,
Not a shy girl

Dear Not a shy girl,
Yes, this is a hard thing to do, encourage a shy guy to ask you out on a date. He's likely so insecure that any type of attraction sends him into ecstasy and any type of rejection will crush him for weeks.

But, if you're confident that he's interested in you, just build yourself up and ask him out to meet for a coffee after work one day. This can even be a spur-of-the-moment idea of yours, meet that day and ask him out for that afternoon after work. Don't give him time to back out of the date and don't plan the date for a few days later in the week so he has all that time worrying about you and him getting together.

Once you start dating you'll see that he's likely one of those "nice guys" that actually has a lot of great qualities about himself, he just isn't used to expressing them in the open, in front of people that he likes and doesn't want to be rejected from.

These "nice guys" all have common personality traits:

easily led to a decision rather than having the courage to make a decision for themselves (often as being talked into something)
has a hard time suggesting things to do
does not lead conversations or even change subjects, just follows the flow of the topic, often not even offering opinions unless cornered into it
often will look at their shoes, hands or over the shoulder of the person they are talking to, rather than look directly at them
neat, cleanly dressed and organized, not overly compulsive
often has loud, overbearing friends, if any friends at all

Once you're dating a guy like this it's easy for you to end up "mothering" them, trying to change them into a "better guy". This is actually not a good thing. Dating someone you mostly like, so that you can change certain habits, styles and traits usually ends up rather messy. Don't date to change someone but be a positive influence on the shy, timid guy and you can effect change through conversational support, nice clothing gifts and style suggestions, even adding hobbies and things to do to build confidence. This is a life-long task, so be prepared to go slowly. Very slowly.

If you have a brother or friend that is showing these shy, timid and "scared of women" traits you can effect positive changes early on by building confidence.

Having hobbies that are interactive (magic) that include performances in front of others is a great way to help break someone out of the "scared of people" mode. As well, there are plenty of confidence building books available. I strongly recommend the "Double Your Dating" ebook for guys.

Best wishes,
Rob

Dear Reader,
Over the years I've had the opportunity to read many "self-help" books that deal with a variety of situations that occur between men and women. Please take a moment and visit these suggested websites, where applicable:

For Women

For Men

* Rob is not a professional counselor, just someone that wants to help. His advice and opinions are his own and should be treated as advice that can be followed or ignored. He'll give you the best advice his experience allows. And you'll have someone that'll listen to your troubles without being too judgmental. And if you don't like his answers, just delete them! *
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Ask Rob! The Advice General