The benefits of dating an older man are very few, and most fathers would have a hard time if their daughters began to date one. To be fair, some couples have successfully lived together despite the age difference. Here are some tips to make your relationship work Dating a wealthy man often brings changes to your social circle. Whether this change is a perk or a problem depends on you. You might find that spending more time with people of a higher socioeconomic group works for you, but you might also feel out of place if your upbringing seems too different from theirs. MillionaireMatch is the largest & original millionaire dating site since 2001. Now over 4 million+ rich and beautiful single women & men are looking for serious relationships.