Hi my sister turned 17 in December, and she is currently seeing a guy who turned 21 a few weeks ago. I have no problems with it at all, neither. I was 17 and had a 21 year old boyfriend (way back when I was that age) My parents were very protective, and the first time I stayed at his they. www.health-o-rama.org › Forums › Life and style › Relationships. My boyfriend is 27 and I started seeing him when I was 19, I'm 20 now dating he's nearly Search for:. My last girlfriend was actually older than me. There is no law that prevents the two of you from dating as in going to the movies, walking in the park, etc. In my opinion yes. I see no problem with it, many girls seem to click here older men! Would you be asking the same question if you were both 5 years older?