Can relationships with significant gaps work?

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36

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Divorced with several children and had plenty of girlfriends.

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Highly educated. Cambridge degree and Harvard MBA.

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Had a high flying career in an investment bank before joining the family business. It isn't your usual corner shop type business.

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Very conservative Asian family. They are well known in the area and have a reputation of being very entrepreneurial and industrious.

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Has lots of expensive hobbies and interests, even his kids are into hobbies that cost 6 figures.

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Has lots of social engagements, often see photos of him with plenty of hot girls posted on Facebook.

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Goes all out and rarely sits about doing nothing. Often seen at the office till 2 in the morning.

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Well presented but not that good looking.

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23

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Still virgin and never had a single relationship.

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2:2 from UWE.

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Dead end jobs.

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Single parent household at your usual council estate. Mum is one of their production workers. English background and doubt he or his parents gives a second thought about their existence.

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Never had any hobbies or interest as never could afford it.

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Not many friends but likes to go out. Rarely happens as no money.

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Like to stay home.

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Good looking.