The largest age gap I've ever seen personally was me and my mate. He is 14 years older than me, for a while we 'dated', which is only in quotes cause to kids these days that wasn't a relationship, we never got physical. But I was with him for about three years, starting at 17, which threw off my dad a bit. Mum didn't mind since it wasn't sexual.
Its hard even to call it dating, it was more like mutually exclusive best mates. But neither one of us expressed interest in others because of the standing relationship, so I suppose it was dating. Lots of films and eating out. It was fun. Taught me a lot about how to be a proper person to the other half of the relationship too, so it was all good.
I should mention though that he was a TBI patient, it left him mentally both my age and older, depending on which part of his personality had been affected. So... not so sure you could really call it a 14 year age gap.
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?the end of our exploring, will be to arrive where we started, and know the place for the first time. - T.S. Eliot