I’ve heard so many different rules about dating someone older, and they all boil down to a magic number: “Don’t date anyone more than ten years older,” or “Marriages never work if there’s more than fifteen years’ difference.” People love rules, telling themselves that abiding by them will cause them to get hurt less. The most important rule to follow is a general one: Make sure the two of you have the same goals for the relationship and for your daily life together. Think about whether you want to get married; have a big or tiny wedding; have children; be with someone who already has kids; live in the future in the same town or city where you’ve been dating; move somewhere far or close; have extended family very involved or not very involved in your life; have a relationship where you socialize almost always together or often; have a partner who’s more of a social butterfly or homebody; and have a partner who is very involved or not very involved in extracurricular activities. Psychological Age You’ve probably heard someone say, “He seems young for his age,” or “She’s so young at heart.” Though we all have a chronological age, we also have what I refer to as a ‘psychological age.’ How old do you feel, for example? In addition, ask yourself what the psychological age is of your prospective older partner. Again, use those early months of a relationship to gauge whether your sexualities are congruent enough.
Don’t embrace any rigid rule about age differences. Don’t be fooled into thinking that just because someone is older, he or she isn’t very sexual.
Are you always up for something fun and spontaneous?
Do you like to feel the occasional rush of adrenaline and stimulation?
(It will never be exactly the same for two different people.) Assess Your Proclivity for Indulgences While many behaviors in the extreme form represent a problem or even an addiction, some of those same behaviors can be harmless if not taken to the extreme.
If so, you either need a partner to like the same things, or you need to find someone who is fine with you doing those things without him or her.
Assess Your Social Circles Take an honest look at your friends and anyone else who is a recurring character in your social life.
Rather than asking him or her such questions directly, lay low and gather your information over time.
If you answer these questions honestly, you’ll have gobs of good information as you try to determine whether a long-term relationship with the older individual could work well.
Assess Your Respective Sexualities Though I find that most people overemphasize the importance of sex and sexual attraction, intimacy is a factor worth considering. You’re not going to a get a true picture about someone’s lifestyle in a month; give yourself a few months of dating to make sure that you’ve seen him or her in as many real-life situations as possible.