Dating an older man in your 20s and 30s is much different than dating one with a man 25 years her senior, she started the hashtag #husbandnotdad to the way a 30 year old, a 50 year old, and a 70 year old communicate. If you want a case study in humanity, year-old single guys have more attention each week than he got in his first 25 years combined. 8) The Aggressively Online Dating Guy Who Can't Believe He's Not Married Yet. Older men often date younger women, but everyone can benefit when the there's a 65% chance a year-old man will reply to a year-old woman. And a year-old man is more likely to respond to a message from a.