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Consider simple questions like, "What do you enjoy doing in your leisure time?" or more specific ones, such as, "What's your go-to hiking spot in the region?"ĭiscuss a shared interest: If you identify a mutual interest, mention it in your message, for example, "I noticed we both have a passion for cooking. Pose a question: Inquiring about something is an excellent means of demonstrating interest and sparking a conversation. Kick off your message by highlighting an intriguing or appealing aspect of the person's profile, such as, "I'm impressed by your taste in music, particularly your fondness for classic rock!" Here are a few examples of how to begin a conversation: Offer a compliment: Everyone appreciates being complimented. Initiating a conversation on a dating site might seem challenging, but it need not be.