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If I was a freshman in college, and she was a senior, otherwise, probably not. Same as top comment: we'd have to be very close in age and student status. If I was a college freshman, maybe it would be acceptable..once you are in college and you see all the hot women around you who are your age or older..would not even care to get with a girl in high school.

College culture is really different from high school culture. But I still probably wouldn't because dealing with her parents, social group, school schedule, etc. A 5 year difference in this case is huge compared to if you were 29 and dating a 24 year old..a 22 year old with a 17 year old is just weird. To be fair though, I'm 24, so even if she's 18 there's a six year difference which I can't help but feel like would be awkward.

Many women who have reached an above-average level of success in their careers grew up in a time when there weren’t that many women in positions of leadership or authority.

Until the last decade, there have been far less female CEOs or women in high-level managerial positions.

For someone who may have had less exposure to women in positions of authority, dating you in your “career hat” can be intense.

If you are tired of dating in your own age pool because maybe those women are immature, or not ready to commit to something more than casual come and go relationships, honor the woman you are with by verbalizing what she means to you and letting her know without question what you bring to the table.

First off, get the age question out of the way up front and don’t let it rule as the elephant in the room. ” Don’t add doubt where doubt does not exist by continually asking him for validation in this area.

This will enable you to feel confident and stop questioning “Am I too old for him? Find comfort and confidence in the fact that he is interested in you, or you would not be having this conversation in your head!

To show your best qualities as a man, and to be taken seriously in the dating pool, compliment your female partner when she discusses her success in her career.

When she shares her stories of how she grew into the amazing creature she is, don’t be shy in holding back your admiration.

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