Come out of the monotonous take-off lines and experiment with words by putting your creativity. If his day was good, then you can let him know yours too. 15 easy ways to start a conversation with a new guy. 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. After all, if familiarity breeds comfort, interest, and intimacy, you can get your foot in the door by simply becoming a familiar face. Starting a conversation with a guy, then, can start out by making your presence a regular staple in his life. People are more likely to respond to you if you ask a question. 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. Dating apps can make it seem both harder and easier to start a conversation like that. Starting a conversation with a guy, that too through text messages, is not for the faint-hearted. The first step is to overcome your fears, anxiety, and other “inner-game” problems. 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. 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. 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. But if he is having a bad day, then you can be there to listen to his problems. Meeting people seems to be getting harder and harder these days. But do not start your conversation like this everyday. 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. Introducing yourself to a stranger or approaching an acquaintance might seem anxiety-inducing, but it shouldn’t be. To check her online profile is one of the best ways to start a conversation with a girl you just met online. It goes without saying, but modify this conversation starter depending on their profile. Asking how his day was is a great way to start a conversation. Keep this in mind when you’re starting conversations online too. There are so many ways to strike up a conversation with someone. Here’s a really great tip on how to keep a conversation going with a guy when there’s a lull and you don’t know where to take it: just repeat the last statement he made. 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. 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