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Her online dating profile caught your attention, but how do you grab a hold of hers? There are two types of questions: icebreaker questions that start the conversation, and questions that keep the conversation going towards the date. To skip to questions to use for back-and-forth messaging, click here. For an icebreaker question to be effective on a dating site or app, it needs to accomplish 3 things:. Not only is praising her appearance a beta male move, she gets tons of messages just like that already.