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You're in your 50s this could be the best time for you to explore new possibilities for your love life, don't be intimidated if you haven't done it in a while, in the end it's just meeting someone, having a conversation, and getting to know them - plus most people who are dating over 50 are in a similar situation. ' or 'Will I need to make an escape plan just in case? That's only natural - everyone feels the first date nerves, no matter what age you are.