5 New Skills for Reentering the Dating Game

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If you're over age 50 and you're truly ready to date again, it's time to take an inventory of what you need to know on this journey. Here are five things you can do to maximize your chances of meeting the right person. (And if he or she turns out not to be "the one," perhaps that person will know someone who is just right for you!)

  • Craft an "elevator speech" about who you are. You never know when you'll meet someone interesting. You need to have a few sentences ready to engage someone and indicate that you'd like to get to know her. Here are a few quick and effective opening lines:

    I work in this building too. I'm with (fill in the blank). What do you do?

    I see that you're not wearing a ring. If you're free, I'd love to have coffee here in the building sometime. (This may seem too direct, but sometimes you only have a few seconds to make a connection. If you're brave enough, this kind of approach can cut through the shyness and get something going — if the person is actually available.)

    I couldn't take my eyes off that (suit, tie, bracelet, hairstyle, dress). You have great taste. Any chance I can get to know you better?

  • Sharpen your eyes and research skills to see who your date is. Face it: You're going to be on the hunt. You need to look at details to see what they reveal about people. Is everything too perfect or just right about the way someone is dressed? Is the person wearing a wedding or engagement ring? Is he friendly to people or dismissive? What do you find out when you research him on the web? You need to find out as much as you can about someone as early as you can.

  • Collect information about the resources and places your city has for singles to meet one another. If you aren't meeting anyone by chance, don't want to go online, and can't seem to get fixed up by friends, then you need to find out more about the singles scene in your city.

    Your house of worship may have a singles group, and most cities of any size have single-affinity groups (Democrat or Republican, for example), hobby groups (skiing, chess, you name it), and commercial activities for singles and sometimes for older singles. Find out about them and get ready to be social — not a wallflower — when you go to a meeting or an event.

  • Find a way to make yourself sound interesting. Figure out what it is you can say, concisely and persuasively, to make yourself stand out from the crowd. Maybe your passion is mentoring adults who never learned how to read, perhaps you're a big brother, or maybe you spent a lot of time abroad.

    Most people do interesting things, and telling someone about that passion is almost always captivating. Even if your job isn't so interesting, recounting the people you've worked for may be humorous and enlightening.

    It's great to talk about a passion, but don't overdo it. Just because you race boats doesn't mean that racing boats is infinitely interesting to everyone. Don't go on too long, and keep checking to see if your partner has had enough. Your date may enjoy your passion too, but don't speak about anything for more than two or three minutes at a time unless you're encouraged to go on.

  • Recruit a good friend to give you reliable feedback about what else you need to know. You're probably not your own best observer. For example, you may think you're being friendly, but a friend may hear your story about how confused you were that your date left early and say that it sounded like you were actually pawing your date and bordering on harassment. Or you may have some clothes you just love, but your friend could veto them as too sexy for a first date.

    A good friend who can go over what went right or wrong is invaluable. If you haven't created a friendship along these lines before, this would be a good time to reinvest in your friends and create a new kind of intimacy. If you haven't talked about dates before or asked for feedback, it can be awkward when you begin doing it. This is not only a good way to get help but also a great way to build a much deeper, stronger friendship.

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