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Avoid These 5 "Older Guy" Mistakes That Chase Younger Women AWAY -Over 40? Do "THIS" Instead

Channel: Bobby Rio
Video: https://www.youtube.com/watch?v=Q-d3XLKIbU8

Five mistakes Bobby says older men make that drive younger women away. He argues the gap between older men who do well and those who struggle is mindset and behavior, not money (you only need to be self-sufficient).

Key points

Five mistakes

  • Putting her on the pedestal. Older men hand a younger woman all the status, assuming her youth and looks outrank them; she mirrors that and looks down on you. Women have historically been conditioned to find older men attractive, so adopt "you need to impress me" and don't make your age weird with self-deprecating jokes.
  • Failing to break rapport. Entering as a mentor/friend (dance instructor, CrossFit, coworker) and never escalating gets you pigeonholed; she won't risk a useful mentorship. Shift from friendly to flirty early with compliments, statements of intent, and light physical contact -- don't blindside her with a move a month later.
  • Buying affection. Lavish gifts, expensive dinners, or helping with her rent/mortgage reinforce her-as-prize, feel like he's trying to buy her, make the relationship transactional, and let you skip being funny, flirty, and sexual. Wealthy clients struggle as much as anyone.
  • Failing tests. Younger women test more to tell the cool older guy from the creepy one -- e.g. a sexual bait (don't pounce) or an age jab (don't justify yourself; joke back). Reframe tests as softballs that let you demonstrate high status.
  • Nice-guy behavior. Men out of a long marriage over-correct on the ex-wife's complaints -- buying flowers, saying "I love you" two weeks in, deprioritizing work -- which kills the ambition/maturity that attracted her. Not making a move reads as fear; women expect things to move fast when there is chemistry. Being a gentleman is fine but does not itself create attraction.

Reception

  • Mixed but engaged; many older men strongly endorse it with age-gap success stories ("48 with 23, no baggage"; a 51-year-old's "think old, act young" essay), and several women commenters confirm they value a confident older man who never put them on a pedestal.
  • A large skeptical camp finds it all too much work and "mind games," with the top comment arguing you should just choose the woman who chooses you, and others saying they would rather pay for companionship.
  • Recurring agreement on the core mindset distilled to "you are the prize," "he who cares least wins," and "have your shit together" rather than money.
  • A vocal minority pushes back that relationships should not be a power play, and that the fix is genuine internal change, not altering outward behavior.
  • Plenty of joke comments (fake "five mistakes" lists, age one-liners) and warnings against trying to turn a younger fling into a long-term relationship.