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“I don't think it is a big deal at all that my boyfriend is 15 years older 6 Women On What It's Like To Date Someone at Least 10 Years Older. I dated a guy who was 15 years older than me, and boy did I learn a few things. If you're considering dating someone older, here's what you. I love a man who is 15 years older than me, and I want to be with him. Will dating someone 12 years older than me turn out poorly for me in the future?.