Dating Older Woman

Remember when a younger man dating an older woman was shocking.  Anne Bancroft was only 36 and  Dustin Hoffman was 30 when The Graduate came out, raising eyebrows everywhere. These days, thanks to celebrity couples like Ashton Kutcher and Demi Moore, it is now kind of cool to be dating a “cougar” (slang for older woman). What do you do to sustain a relationship like this?

Older women are more confident and have a greater understanding of what they want out of life. This is part of what makes them attractive. If you are the younger man used to dating women his own age, it can take some getting used to. Older woman don’t need to be lead, but they do want you to be confident.

She will likely be more accepting of your independence,  your alone-time and with you seeing your mates. Your older woman has developed a strong set of social relationships and will want more time alone  and with her friends than women younger than her. You can relax and go watch sports with the guys without being worried about an upset girlfriend.

However, she knows what she likes and she’s going to be less tolerant of sloppy house and hygine. If you really want this relationship to work, you are probably going to have to do some maturing of your own. An older, secure woman wants a presentable man and doesn’t want to hear about your latest set of scores on Madden Football. Educate yourself on the things she’s interested in and the things she likes. If you want to be with her, you’ll need to know who you are, what you like but you’ll also need to understand where she’s coming from. Try and understand her season of life. If she’s done with student style living, then you’ll need to understand that and live the kind of lifestyle that’s now appropriate i.e. not living in a stinky crash pad that resembles a teenage boy’s room.

There will be generational differences in pop culture. This isn’t always true, but understand that you both will have different points of reference when it comes to television, music and film.  Don’t think she won’t need reassurance about the age difference periodically. Build her self esteem, be your best self (true in all relationships, right?) and this could be the relationship you’ve both dreamed of.

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