Dating After 50: Practicing Some Date Night Phrases

If you were asked, “What's the hardest part of starting to date again after 50?” you might say that it's becoming comfortable initiating contact or showing interest in someone else. The very beginning of contact is full of suspense. Will she accept an offer for coffee? Will he respond to an invitation to a play? How do I show I'm interested without looking pathetically interested?!

That said, planning a mutually comfortable and fun first date and figuring out a way to make yourself memorable (in a good way!) doesn't happen automatically. Many people (including many experienced daters) flounder when it comes to conversation and modern date etiquette.

Make sure that you feel secure about having a successful first date by practicing a few appropriate date night phrases, conversation topics, flirting, and finding the right activity.

Flirtatious phrases

Here are some flirtatious phrases that you should use only if you really mean it:

  • “You have great eyes.”

  • “You have perfect skin.”

  • “You’re incredibly handsome.”

  • “You look a lot like — [movie star your date really looks like].”

  • “I think you’re so attractive — much more attractive than your picture.”

  • “I can’t stop staring at your lips.”

  • “I love your hair.”

  • “You’re incredibly sexy.”

  • “Those are really sexy shoes.”

  • “I love the way you dress.”

Market yourself in a safe and winning way

You want to be real and authentic. It serves no one if you pretend to be someone you're not. But be yourself on a good day rather than a bad one. Don't oversell who you are — and don't undersell! Be patient and let information flow as appropriate over time.

Overselling Underselling
I bought and sold two companies last year. I went bankrupt during the recession; I just couldn't save the company.
I'm a take-charge kind of person. Give me a problem and I can solve it. I'm just an average kind of person.
My children adore me. I don't know how parents do it. The teen years were an awful time.
I've never had a sick day in my life. I just can't hear or move like I used to.

Reveal some accomplishments, but don't overdo it. Don't list all the great things you've done, and certainly not all the great things you own. You don't want to come off as an egomaniac. Playing Donald Trump doesn't look good on anyone, including Donald Trump.

Find the right level of activity

When planning a first date, it’s important to correctly gauge what level of expertise or athleticism is comfortable for both you and your date. You don’t want to be so exhausted that your primary feeling is frustration or even anger. That’s not the feeling you want to develop here!

Just to make sure that dates don’t try to please you so much that they take on something above their ability to enjoy, here are a few questions that may help you know what kind of activities are appropriate. You can add a few more for a specific sport that you know well if you think it’s safer to probe a bit deeper.

For example, if you’re thinking about kayaking in open water, ask whether your partner has taken some kayaking lessons. That will tell you a lot about how experienced your date is. Here are some questions to ask to gauge the ability of your date so that you pick the right level of activity (and be honest about your own ability!):

  • How long have you been doing this?

  • Tell me about some great experiences you’ve had doing this.

  • I’ve taken on a few things I shouldn’t have. Have you?

  • How long do you think an optimal time out would be?

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