How To Date Older Women

When considering dating an older woman, there are a few things that should be self-assessed first:

1. Are you mature enough?  Older women, while some may find immaturity cute, typically want some level of moderate maturity in a man.  They expect to be able to hold a conversation that doesn't involve video games, drinking, partying, or sex at least once a day.
2. Assess your living arrangements.  If you're living at home with your parents, it's probably best that you not seek out an older woman for companionship just yet.  Depending on how much older she is, it can make a woman very uncomfortable to find out she's nearly old enough to be your mother or that she has more in common with your folks than with you.
3. Assess your livelihood.  What does your employment situation look like?  If your income isn't impressive, but your work is admirable, this can suffice.  If your income isn't impressive and neither is your work, this could be a problem. 
4. Why do you want to date an older woman?  Older women typically do not want to waste a lot of time.  Some may be divorced, with or without kids, or maybe past their prime.  If you are not looking for a serious relationship, it's best for all involved that you don't waste her time. 
5. Can you handle an older woman?  Some older women are quite experienced and know exactly what they want from a man.  If your manhood is going to suffer from a little criticism or instruction, this is something you should strongly consider.  On the flip side, other older women don't know what they want and after a lifetime of bad relationships they may require patience and understanding, as well as constant reassuring that your interest in her is genuine.
6. Finding an older woman to date can be relatively simple.  Getting an older woman to want to date you can be significantly more difficult.  By preparing well, knowing what you really want, being open and honest, and constantly reassuring you can successfully manage a relationship with an older woman.