Older women are more likely to have built-up assets, including one or more homes, businesses and stocks. It can intimidate any man when a woman is worth more money than he is, and this is especially the case of a well-off older woman dating a younger man. The key to getting past this issue is seeing how you feel: If the woman does not hold her assets or success over your head or expect you at your young age to match her success, then there is nothing to worry about.
Older women are more likely to have children from previous relationships; this is especially true of women over 40. This isn't always an issue, as many times the woman's children are grown. However, when the woman's children are still minors, living in the home or are the age of her younger partner, problems may arise. The only way to work through these issues is by talking to your partner and assessing whether you can accept her children.
Since they have had longer careers and more time to become financially stable, older women commonly own their own cars and homes. Younger men, especially those younger than 25, don't usually own much property. This can present an issue: Is the younger man just using the woman for what she has? The way to show your partner that you are in the relationship because you want her and not what she owns is to avoid accepting gifts or loans from her. Also, if you decide to move in together, you should be splitting the bills equally.
Though each woman is different, older women are usually experienced when it comes to relationships and therefore don't like to play the "games" some younger women do. They don't typically go checking after their men to see where they're at, and they don't try to make their partners jealous in order to seek attention. Older women tend to know exactly what they want out of a relationship and are not afraid to make it known. Expect her to openly communicate her needs to you, and prepare to do the same--it is what mature adults do.
Since their children are usually grown and they are financially stable, older woman choose different activities to do in their free time than younger women. Many older women like to travel in their free time--some prefer international destinations, while others simply want to see what all this country has to offer. Being the partner of an older woman, she may ask you to join her on her travels. If you accept, it is best that you pay your own way. This avoids confusion as to whether she should be paid back after fronting the costs of the trip, and also keeps her from feeling like she's being used.