Traditionally, women are pursued in the dating world. The unwritten laws of relationships have made it relatively easy for a guy to start things with a girl: he asks her out and she says, "Yes," right? But what if the object of your attraction is super shy? It may be time to step up your game and woo the guy of your dreams. There is nothing wrong with putting effort into getting exactly what you want.
Don't waste your time daydreaming about the moment that he finally gathers up enough nerve to talk to you. Put on a smile and approach him. A kind smile and a modest greeting will get his attention. Start with small talk, such as, "Haven't I seen you in one of my classes?" Once you break the ice, he will likely open up more and more.
Talk to Him
A shy guy is not going to open up readily. Be persistent, but give him his space. Once he gets to know your great personality, he will look forward to hearing from you at every opportunity. If after a while he still has not asked you out, ask him out, or suggest you both go somewhere casual with a group of friends. Do not put pressure on him to accompany you to an intimate setting. Being somewhere fun and comfortable will put him at ease so he can show his true colors.
On the First Date
Asking too many questions will provoke anxiety in a shy guy. Feel free to talk about your interests and hobbies, but leave the conversation open for him to talk. Shyness is best treated with familiarity; the more he gets to know you, the more comfortable he will be around you. April Masini, an author and relationship expert, states in her article "Dating Tips for Shy Guys" that jokes and humor can help bring out his true personality. If he is laughing and smiling, he is more likely to open up than if you are constantly trying to be serious.
After a few dates, you should see your guy opening up. He will be talking more about himself and may even be asking you out. Be accepting and gracious of his offers. His fears of rejection or insecurities can easily be put to rest by your constant acceptance. It is natural for men and women to be taken over by shyness at the beginning of a relationship. Make him feel comfortable and show your interest. You'll have that sweet, shy guy wrapped around your finger in no time.