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By the time you have your first child, you’ll be 38 or 39. That’s not the kind of life you imagined for yourself or your children. Let’s just hope that they don’t discriminate against men their own age.

You’re a successful older man who wants to date a woman significantly younger than him. Needless to say, this goes for ALL people who are dating online. We want what WE want, even if what we want is unrealistic.

Websites generally attempt to pair singles with matches who are demographically similar. We’re all so dazzled by looks and youth that we pass up amazing people who are a much better fit. The woman who graduated high school in the same year as you? “I can’t help what I’m attracted to,” say all of my clients – both male and female. I do know, however, that as long as they close their minds to dating people who are age-appropriate, they’re really going to struggle with online dating.

Alright - so a little background on whats happening...

I am recently single after an 11 year relationship (8-1/2 years of marriage) ended.

Minaj dated Nas for several months before splitting back in December, she famously dated Meek Mill prior to that.

EDIT: This may get a bit long - but I promise a fun ride!Essentially a light version of ‘catfishing’ – when you pretend to be a totally different person online – kittenfishing can be as simple as using profile photos that are out-of-date or heavily edited.Or it can be more severe, like straight-up lying about your age, height, interests or accomplishments.This question is exactly why I’m on a dating hiatus at the moment, since I just can’t bring myself to seek out a much older man, or play the cougar.The world of dating can be brutal and if you’re one of the singletons trying to navigate your way through the scene, the chances are at some point you’ve been ghosted, breadcrumbed or even benched. How does a 56 year old man find a good younger woman that would be interested in marriage and willing to have children by him? Most good sites line me up with the 50 year olds and most 36 year olds tend to think I’m a dirty old man.