9+ Things to Talk about with a Guy You like to Understand Him If you think it’s hard to find things to talk about with a guy you like then you are in the right place. Asking how his day was is a great way to start a conversation. Starting a conversation with a guy, that too through text messages, is not for the faint-hearted. Come out of the monotonous take-off lines and experiment with words by putting your creativity. After all, if familiarity breeds comfort, interest, and intimacy, you can get your foot in the door by simply becoming a familiar face. To check her online profile is one of the best ways to start a conversation with a girl you just met online. If you struggle to keep a convo going, simply by saying the last phrase of what someone has said — especially if he’s a talkative person — will make him continue the conversation. The first step is to overcome your fears, anxiety, and other “inner-game” problems. Introducing yourself to a stranger or approaching an acquaintance might seem anxiety-inducing, but it shouldn’t be. It goes without saying, but modify this conversation starter depending on their profile. But if he is having a bad day, then you can be there to listen to his problems. If you want to start a conversation with an interesting guy, whether it is online through sites like MSN, Facebook, face-to-face, or text, I have a two-step formula. However, besides the conversation starters you will need a lot of courage too to simply walk up to a guy and start talking to them. But do not start your conversation like this everyday. Occasional pick-up lines would also work better, but shouldn't sound too cheesy and give him ample reason to put-off the talk even before it gets started. Depending on your personality, texting may be easier or more difficult than an in-person conversation for you. Give attention to how he is responding and ask him more questions accordingly. 15 easy ways to start a conversation with a new guy. It’s hard to reach out to someone knowing you’re both potentially attracted to each other, but the important thing is to remember that you should be yourself, be genuine, and not be creepy. Let’s face it: starting a conversation can be intimidating.Whether you’re meeting a total stranger, trying to network, or on a first (or even tenth) date, it’s often difficult to know what to say to start a conversation and keep it flowing. Keep this in mind when you’re starting conversations online too. With our phones being the number one form of communication nowadays, knowing how to start a conversation over text is vital. If his day was good, then you can let him know yours too. People are more likely to respond to you if you ask a question. 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