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But he does leave a trail of red flags if you take the time to look for them. How to Approach a Guy. Jag Carrao, Contributor Dating and relationship coach. This is not only a painful dating game, but it is often a red flag for serious emotional abusive relationships. For some reason, Tiffany expected Troy to give her a call the next day. How can you tell if someone is playing hard to get or if they are just not interested?