Dating After 50: How to Introduce Your Date

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When you’re dating again after 50, what should be the order of introducing someone to the people you care about? Here's the order that makes sense in terms of feedback, difficulty, meaning, and purpose.

  1. Your best friend(s).

    Your closest friends want the best for you and want you to have whatever it is you want. They won't try and deep-six something just because it gives them less time with you or because you're not the person of their dreams. (If they're not this kind of person, perhaps you need to reevaluate the friendship!)

    So they're the likeliest people to root for you and hope that your date is worthy of you. They may have an inflated sense of your “worth” (God bless them), but with that in mind, they're still the best first introduction.

    They'll give you kind feedback (even if they think you're utterly deluded, they'll say so nicely), and if they really like your date, it will shore up your courage to move down the list to other people whom your date would like to meet and whom you want your date to meet.

  2. Your crowd or friendship circle.

    Eventually, you'll want to see how your date fits in. She doesn't have to like everyone in the group (you probably don't even like everyone in your friendship circle!), but your group is a good testing ground to see whether your date sees people the way you see them and mixes easily with the people and events you like the most.

    People in your crowd may or may not give feedback, but because you have differing levels of closeness with them, many of their opinions don't matter that much.

    If you don't have an extended group of friends and acquaintances, take your date to an event where you know people to see how she adapts and works with you in a couples situation.

  3. Your siblings.

    Your date is going to be very interested in your brothers and/or sisters if you have any — especially if you're close to them. They're a big clue to who you are (and are not), and your date will be very concerned about making a good impression if you tell her that you're close to your family.

    If your siblings are judgmental or treat your date indifferently, your date may wonder how many times you've introduced someone. If your siblings act like your date may become one of the family, it will raise expectations (or fears, depending on your date's state of mind), so basically, whatever way your siblings act will be meaningful.

    Introduce your date to your friendliest, least-judgmental sibling first. That person is likeliest to send around a good message about you to the rest of the family.

  4. Your children.

    Your children may be excited and happy for you. However, they may be happy simply because you're dating but not necessarily satisfied with the person you're seeing.

    And you may face a situation that really causes fireworks if your kids think that you're desecrating your deceased spouse's memory or if issues from a divorce rise again and your children and ex-spouse become enraged.

    Consider putting off this introduction until you feel it's important enough to both of you to brave whatever happens. If you're positive that your children will be thrilled with your date, you can move the introduction up a bit. But be cautious: The reactions of children aren't always predictable.

    Don't tell your children things that should never, ever be said, such as, “Don't worry, this isn't ‘the one,’” or “I'm just dating, it's nothing serious.” Relationships can change in nature, and you may fall in love with your date — and then hear your children throw those statements out to your beloved if they aren't happy with this person.

  5. Your parents.

    Your parents are probably quite interested in meeting your date, unlikely to curb their opinions, and perhaps worried about this new relationship. If your relationship is getting serious, your date will probably want to meet your parents. If you think this may be difficult but want to honor the request, set up a brief visit to start.

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