People are more likely to respond to you if you ask a question. The first step is to overcome your fears, anxiety, and other “inner-game” problems. With our phones being the number one form of communication nowadays, knowing how to start a conversation over text is vital. 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. Give attention to how he is responding and ask him more questions accordingly. Depending on your personality, texting may be easier or more difficult than an in-person conversation for you. Come out of the monotonous take-off lines and experiment with words by putting your creativity. 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. 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. 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. 15 easy ways to start a conversation with a new guy. But do not start your conversation like this everyday. 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. Starting a conversation with a guy, then, can start out by making your presence a regular staple in his life. If his day was good, then you can let him know yours too. It goes without saying, but modify this conversation starter depending on their profile. 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. Do not fall for the dumb starting line when you want to message a girl you don’t know. 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. After all, if familiarity breeds comfort, interest, and intimacy, you can get your foot in the door by simply becoming a familiar face. 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. Introducing yourself to a stranger or approaching an acquaintance might seem anxiety-inducing, but it shouldn’t be. 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