Your friends are at a completely different part of life than his friends, which is probably one of the leading factors of what makes this so difficult. This isn’t to say that it isn’t worth it, but it's just another challenge in the already difficult dating world. The amount of life experience at each decade is incomparable, which is why dating someone much older or younger than you can, sometimes, be difficult. Dating means something quite different when you're in your teens, your twenties and your thirties.
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