Dating After 50: What to Do Together

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After the first couple of coffees and perhaps a few dinners or movies, you'll start to discuss things that each of you likes to do, and you'll eventually introduce each other to some new activities.

First, of course, you'll try to find mutual ground — and hope that you have enough in common so that you'll have an immediate advantage of mutual interests. But probably sooner than later, you'll want to see what it's like to explore someone else's world.

The trick of this is to try things with an open mind that you may have rejected in the past but not talk yourself into something where there's a 99 percent chance that you'll hate it, be afraid of it, or resent your date for getting you into this situation!

Try out the things your date likes best

Suppose your date loves in-line skating (or some other sport) and you've never done it. In fact, it scares you a bit. On the other hand, you'd kind of like to try it. Should you? Sure, but here are some guidelines to observe:

  • Are you able to try this activity without getting hurt? In your enthusiasm for your date, you may try something that you really aren't good at and hurt yourself. Breaking a wrist or ankle isn't romantic and can really derail a promising beginning to a relationship. If you're uncoordinated or really don't like athletics very much, don't make this your first foray into new territory.

  • Do you think there's really a good chance that you'll enjoy it or will you have to pretend you like it? Don't start out your relationship on a false premise. You may like to please your date by doing something she likes, but then she may assume this is a shared common interest, and you'll eventually have to try and find a graceful exit from these kinds of activities, which makes you look less than authentic.

  • Are you willing and able to be the student for an evening and follow your date's lead? If you're going to do something your date likes, she'll probably take the lead and decide on the date's details. You have to give up some control and trust that your date will shape the day or evening in a way that's comfortable and appropriate for you.

    If you're unsure whether your date knows you or your abilities well enough to pull this together in an agreeable way, you may want to beg off on this type of date until you're sure it will turn out well. Don't forget, though, that taking a stab at things you don't do well has comic potential and can create a lot of laughs between you, which often creates a very endearing situation.

Introduce things you usually do

Sharing something you love with someone you're interested in can be exciting, but you want to make sure that you don't take your date too far out of his comfort zone. You also don't want to make this into a de facto test of suitability. Here are a couple of pointers for introducing activities to your date:

  • Do a very basic version of what you do.

  • Engage in the activity for only a brief period of time; if your date wants to extend it, he can, but don't push it.

  • Reassure your date that if he doesn't like it, it's no big deal.

  • Try not to be too much the expert; your date may like some teaching, but do it with a light hand.

Try out things neither of you have done

In some ways, trying out things that neither you nor your date has done before, which I discuss in the next section, is the safest choice.

Discovery together is fun. Neither of you is on your own turf, so you learn together and can lean on each other without one person being the teacher and the other the pupil. If you don't like something, it's not a reflection on the other person — you just move on to another choice.

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