However, these feelings of insecurities in normal people are different I don't trust people who don't love themselves and tell me, 'I love you. If you are on a date with someone in within the first hours you hear these things No one wants to date an insecure person who is suffering from past. If you're dating someone who is insecure, there are some definite dos and dont's to ensure a successful relationship. Read on. We don't like talking about ourselves. We get that dating someone who is insecure can sometimes be a handful, so thanks for even wanting. Here's how to navigate dating an insecure dude, and how to know when you understand why certain things affect him when others don't. Make no mistake: There are ways to deal with someone you love being insecure. Even though we know we should avoid it, the bad-boy charm is sometimes impossible to resist.