Be Honest About Expectations
Depending on the age gap, your expectations may differ enormously from those of your date. For example, she may be interested in dating a few people while you are unfamiliar with this approach to dating. The only way to mitigate the effects of the modern, liberal approach to dating is to be open and honest about what you expect. If you are looking to start a serious, exclusive relationship be clear about this from the start.
Play to Your Strengths
Differences in lifestyle may become a problem if not properly addressed. For example, if you have a full time job and the person you date is a student, late nights are not as convenient for you. Your energy levels may not be what they were and you might find yourself struggling to keep up with a hard-partying youngster. Don’t attempt to keep up. Instead of attempting to party harder than you really want to, politely decline the offer and instead arrange to go for dinner. Your age and experience mean that you are likely to be more comfortable and relaxed in a more sedate environment. Don’t view this as boring. This sort of sophistication is one of the reasons young women are often attracted to older men.
Don’t Ignore the Age Gap
Trying to ignore the fact that you are significantly older is pointless. It will create awkwardness. At some point an issue will come up where the difference in age can’t be ignored. You may use a “before her time” cultural reference which is completely lost on your date. Celebrate these differences; don’t hide them. Embrace the opportunity to learn about new artists, musicians and social trends.
Find Common Ground
It’s important to find shared interests. There’s no age restriction on who can enjoy a movie or a wine-tasting course. Look for activities which are not age-specific.
Respect Modern Values
If you are more than 20 years older than your date, it’s likely that certain customs and trends have passed since you began dating. This is especially pertinent if you've been out of the dating game for a long time. Speak to younger friends about how dating has changed and find out what is expected of you in terms of dating etiquette. Manners are great, but overt chivalry is a little old-fashioned. Don’t insist on picking up the check if your date offers to pay half. Explain that you’d like it to be your treat, but don’t be pushy. Hold open the door because it’s polite, but don't get to your feet each and every time your date goes to the bathroom.