How to Deal With Being in a Relationship With an Older Guy

All relationships have advantages and pitfalls. May-September relationships (where the man is significantly older than the woman, usually by at least a generation) have their special challenges. Knowing what to expect can make the difference in the relationship.

1. 1

   Determine why you are choosing someone older as a relationship partner.

   • Sometimes the relationship is a superficial one, based upon the man’s financial situation. This stereotype is seen often in the media, and therefore makes people immediately think that if you’re with an older man, it’s because of his money.
   • Other women prefer much older men because they are attracted to the knowledge, experience and/or wisdom that comes with those years.
   • Still other women prefer older men, but only if they appear to be younger than they are. This helps negate some of the “gold digger” comments.
   • Still other women choose older men because they had an unhappy or nonexistent relationship with their father, and are trying to fill that hole they feel in their lives.
   • Other women have a “caretaker” instinct that draws them to older men who genuinely care and appreciate their kindness.
   • There are also women who are sexually attracted to men with wrinkles and gray hair.
   • Older men tend to be more grateful for their relationship with someone younger, and are somewhat less likely to cheat.
2. 
   2

   Realize that you’ll have to deal with prejudice.

   • You’ll be mistaken for the man’s daughter or granddaughter on occasion.
   • Prepare to hear people humming “You’re Sixteen” and “Don’t Stand So Close To Me” near you.
   • Some friends will immediately think your boyfriend is creepy and will think you crazy for dating this man. You may have to convince them of his good qualities.
3. 
   3

   If the relationship would be an illegal one, strongly consider the consequences.

   • This means that if you’re under 18, you could be subjecting the person you want to date to possible criminal charges. Even your consent is not enough to overcome statutory rape. It is in the man’s interest that you keep the relationship platonic until a romantic relationship is legal.
4. 
   4

   Remember to include your boyfriend in some of your activities, and let him know that he’s welcome to include you in some of his activities.

   • This will help people see that you two are not just a “secret” embarrassing item, but that you two actually do have a relationship built upon attraction, respect, trust, and shared experiences.
5. 
   5

   Think about the future, especially if you consider marriage.

   • If you want to start a family. An older parent isn’t necessarily a bad thing … children are born to parents who are in their 40s.
   • If you’re in a March-November relationship instead of a May-September relationship (a 2-generation difference) then you need to prepare for the very real possibility that you will outlive your partner while you are still young or early middle-aged. Be sure end-of-life concerns are taken care of for your partner, and that you are emotionally ready for the stress: both during the relationship and after.
6. 
   6
   If you two really do love each other for the right reasons, most people will eventually accept your relationship. Those who don’t either can’t see past their prejudices or don’t care about your happiness.

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