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Do’s and Don’ts for Dating Shy Guys. Nick Slade Updated: 10/09/ Discuss This! You’re a lady. THE LATEST ADVICE. How to Meet a Good Woman. Hunt Ethridge, Men's Dating. 10 Questions to Ask Your Boyfriend. Rachel Dack, Women's Dating. How to Choose a Dating Site Username That Works. Advice for Shy Guys: 13 Things About Socializing I Wish Someone Had Told Me When I Was I spent my early 20s learning social lessons the hard way. Jun 15,  · Tips for Girls Going on a Date With Shy and Introverted Guys. Updated on November 28, princesswithapen. From tips on flirting with him to kissing him and from advice about the clothes you should wear to giving him a hug, this post gets straight to the point. Helpful points here on dating shy guys, definitely these tips can help Reviews: 3.