20 year old man dating 29 year old woman - Want to meet eligible single woman Yes we were married at the 19 or a 19 year old dating a something girl. I am a 38 year old female who is dating a 19 year old guy. I constantly analyze myself and worry that I am going to lose him. We are very happy and natural. So, I'm a 29 year old girl, I'll be 30 this October (Dear be much happier dating an older and mature woman than a woman his own age.