Pros to dating pros to dating an older man an older man. free online dating sites in houston. however those men are few , the reality is, far in between that does make having a relationship with an older man the better choice for most women. either way there are pros , cons to being in a relationship with an older man but the same goes for dating anyone of any age. the advantages of dating an older man are plenty. if you are tired of the games of men your own age, you will be pleasantly surprised because young women dating older men have a lot to look forward to.