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Instead of trying to flirt by opening up about yourself and attempting to impress someone, ease into the conversation by asking questions or asking a favor.For example, you could say, "I like that dress, where did you buy it from?" This requires the other person to invest into the conversation first, and can work as just the ice breaker you're looking for to overcome your hesitation.

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If you're at a restaurant or bar and see someone that you want to get to know more, try sending over a drink or a plate of appetizers to the person's table.Generosity is a nice token that can help spark interest in the other person.Plus, sending over food or drinks requires no immediate physical or verbal contact, which often gives shy guys cold feet before they even start flirting."Flirting is a key step toward initiating a date," Dr.Sean Horan, a faculty member in the College of Communication at De Paul University, tells "Psychology Today" magazine.

Alas, shyness, social anxiety and the fear of rejection can make it difficult, if not almost impossible, for a shy guy to break the ice and flirt with someone.Don't give up hope as you enviously watch your outgoing buddies work a crowd!Several flirting tips can help you initiate a conversation and express your romantic interest, even for the most shy and subdued among us.When you're a shy guy, "putting yourself out there" in the flirting game often gives you the chills.At their core, it's often hard for shy people to open up and initiate a conversation due to a fear of failure or rejection.In essence, breaking the ice "gives the other person all of the 'power and 'influence' in the situation," writes psychologist Jeremy Nicholson for "Psychology Today" magazine.