How To Date an Older Woman

Dating Help and Relationship Tips for Younger Men

Giving roses

The key thing to remember about dating older women is that age is truly just a number. Compatibility and open communication are much more important for a successful relationship, not calendar years. You are first and foremost dating a woman, someone who expects the same level of respect you would show a younger woman or someone your age. 

Here are some dating tips for dating older women successfully.

  1. A generation gap doesn't have to be a bad thing. She may have been a senior in high school when you were still in middle school, but you both experienced the same music, movies and other pop culture events. Even if the age gap is larger, you can still have pleasant conversations about the different concerts you've seen or the movies you remember from childhood. An older woman may not mind sounding like the experienced person she is, as long as you respond intelligently. Never use her own words as an opportunity to tease her about her age.
  2. Older women often display more confidence than younger women, simply because they have had more experience with dating and know how to hold their own in any conversation. But many of them still have the same insecurities as any other single person trying to make a good impression. When dating an older woman, it helps to be extremely complimentary about their outfits or hairstyles or makeup. Men may not realize how much anxiety can be generated when an older single person compares herself to all of her younger and firmer competitors in the dating world. Make your date feel truly beautiful by pointing out her best features and assuring her that she is just as appealing to you as any other woman in the restaurant.
  3. Keep in mind that older women have often had harsh dating experiences or even difficult marriages in their past. You may think you're being funny by teasing her incessantly, but you may actually be reminding her of a former partner who didn't know when to stop. Find out what you can about your date's previous experiences with men before you inadvertently offend her. If an older woman doesn't want to share information about a former husband or boyfriend, don't push. Steer the conversation back towards something more pleasant.
  4. Don't be so concerned about your own youth and lack of experience. If an older woman agreed to go on a date with you, it's because of some special quality you displayed. She knows you're younger, but if the age gap doesn't bother her it shouldn't bother you. There's no need to act especially mature for your age, but try not to take a step backwards socially. Be every bit your own age and allow her to be a little immature if she wants to be. The first few dates are awkward for any couple, and she may need some time to figure out an appropriate level of maturity.
  5. There are some definite social benefits to dating an older woman, but remember to be a gentleman at all times. She may already have an established circle of older friends who may or may not accept your relationship. If you have the opportunity to introduce yourself to her friends, demonstrate a level of maturity that matches your relationship. What her friends may want to see is true compatibility and compassion. They understand her past better than you do, so don't be afraid to take things a little slower than you would with a younger partner.

These relationship tips are only useful if you are serious about your relationship with the older woman. If you merely want a one-time trophy date, then move on to a more meaningful relationship with someone your own age.


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