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First Dates After 50: The Complete Guide to Early Dating

If you're over 50 and standing at the edge of dating again, first dates feel enormous. More than they did at 30. More than they probably should.

That's because at this age, you know things. You know what a bad relationship costs. You know how fast years go. You know you're not doing this for practice anymore.

Which is exactly why I want to give you every advantage I can.

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Post-Divorce Casual Dating: To Fling or Not to Fling?

Two of my three kids are grown, so I think I can safely say now that I wish they had taken a gap year between high school and college, or during college. At least they studied abroad.

The amount of worldly knowledge and independence they gained from studying abroad got me thinking about the corollary to dating after divorce.

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Unpopular Opinion: Men Over 50 Deserve a 2nd Chance

I don’t mean get back together with the man you divorced.

I certainly don’t mean stay with someone who abuses you.

I mean, in early dating—even in texting. I mean, when something rubs you the wrong way and you’re ready to call it quits before chemistry has had a chance to develop.

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What to Expect When Dating a Man Over 50

If you’re a woman in later years looking for a mature man around your own age, there are some things you should expect. This list isn't meant to scare you—it’s to help you experience the dating scene with greater ease.

First off, they might help you feel less crazy, because if you’ve been dating, surely you’ve noticed them!

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Why Your First Date Should Be a Video Chat

If you met online, your first date should not be a glass of wine at a noisy bar. It should be a video call. Full stop.

I know, I know. It’s not the fantasy. But we’re grown-ups now. With real-time energy levels, complicated schedules, and no time (or patience) for last-minute (or during-date) disappointments.

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The Do's and Don'ts of Dating Site Prompts

You finally open up the dating app, and there it is—the blank box next to "What makes you unique?" You freeze. Is this the best place to share your love of New York bagels? Is it too soon to mention your three divorces and obsession with Candy Crush?

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How Honest Should You Be on a First Date?

Let’s brush our teeth before we kiss, he said on our first date, implying I had bad breath! 

I was mortified. But I brushed my teeth, and we had a great first kiss.

That was decades ago, and now we’ve been married 27 years. When asked how I knew he was the right person, I harken back to that bold, brave, risky thing he said to me.

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3 Do’s and Don’ts of Online Dating Banter

When you first spot someone on a dating app and your interest is piqued, the next big step is kicking off some fun, flirty banter. Since they can’t read your body language, your online banter has to carry all the weight of making that initial spark happen.

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Are You Undateable?  6 Things You May Not Realize

If you’ve ever secretly Googled “Am I undateable?”—first of all, hi, welcome, you’re in good company. Second, the fact that you’re asking that question probably means you’re not. Truly. 

Single women who are reflective, curious, and willing to assess their love life honestly are usually very dateable.

But. (Yep, there’s a but.)

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