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He makes the mistake of bringing the issue up before she has, or cracking awkward jokes about her youth.
His age insecurity will lead him to lean on his money or job status as attraction ploys because he won’t believe that a cute younger girl could love him for his personality or strength of character.
If she sees three or more girls laughing along with you, bonus points. If 29 year old tells you some random guy flirted with her today, show a hint of jealousy.
An older guy who is needy is a bigger loser than a younger guy who is needy, because the younger guy at least has the excuse of inexperience.The truth is that, contrary to the sugar daddy cultural message, money and a high status job are not required to attract younger women.