It’s important not to make assumptions in dating, especially in the areas of sexual expectations and gender roles. The way you and your date communicate about and focus on the future will dictate compatibility. Many older daters feel more sexually liberated and confident than in days of their insecure, inexperienced youth. Try to avoid talking about exes on the first date — or at least mention them only in passing and without bitterness. If you’re nervous about meeting a stranger for dinner, opt for a daytime date. Sure, you should show up to dinner solo, but don’t start dating again without letting loved ones know.
Perhaps the greatest difference between dating in your twenties and dating in your fifties is the way you see and talk about the future. Others are paralyzed by body issues and are terrified of being with someone new. Bitterness is often the greatest criticism from older daters. If you’re overwhelmed by someone’s affections, explain that you need to move slowly. Not every person you date has to be “the one.” Besides, there’s no more ticking of that biological clock; instead of dating out of a sense of urgency to marry and have kids, you can slow down and ensure that you’re in a relationship for the right reasons. Tell your friends you’re ready to meet someone, and welcome them to set you up.
Dating is still about getting to know someone, taking the time to see if you connect spiritually, emotionally, intellectually and physically. From early on, be intentional about showing real interest in the other person and getting to know one another as transparently as possible.
Most of that age-old advice is as pertinent as ever: Be yourself, smile, keep an open mind, and be honest.
After 23 years of marriage, however, I learned a thing or two.