How to Move Dating from the Phone to the Real Word in Covid Times

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Hey Wendy,

My job changed so I reached out to a guy I briefly connected with online years ago to ask for some advice. We never met in person back then. Since reaching out, he’s been calling me and has reignited the connection. We’ve had several very long calls.

He said something painful to me, “You must be really happy you never got married.”

I wasn’t sure why he said that. (ouch!) but I responded with my elevator pitch like you taught me, and that was it, end of question. He was married 30 years. I have never been married, unencumbered, still looking for a life partner. It’s a top priority and I did not go there.

I’m enjoying getting to know him. I’m starting to bond over the phone. But I don’t know how to address this issue so I’ve said very little, and asked few questions. Because of Covid it’s obviously a weird time to meet in person.

I feel like this budding friendship with a very nice guy is skidding off the rails because I haven’t communicated my feelings in the right tone with grace, ease and femininity. Your thoughts?

ps….I bought your Ready for Love Toolbox, and love it! I love listening to you.

Xo- Bette R.


Hey Bette!

Thanks for being a fan!

I’m so glad you wrote. You, my love, are overthinking this. Hard.

It’s Covid.

It’s weird.

We’re all a little weird right now.

No one is 100% okay.

So, you’ll want to give him a break and you’ll also want to give yourself a break.

“You must be really happy you never got married” was likely a fishing expedition rather than an insult. He’s trying to learn who you are, what you’re about, and what your relationship to freedom and partnership is as he proceeds. It’s unusual for a woman to be single most of her adult life. It shows you have a level of discernment and a willingness to be happy on your own that not everyone has. This is intriguing.

If his assessment in the statement is wildly inaccurate, it’s okay to be vulnerable with him and share what your life has been like. Rich, deep, meaningful conversations only happen when we’re willing to be vulnerable. So, take a chance and share, to tell a story or two. Let him know the sticking point (or points) that had you saying “no” in the past.

Now, before I go giving my next piece of advice, we need a disclaimer: What I’m about to suggest as an option has risks and may not be effective in preventing the spread of Covid-19. I guarantee nothing here. Okay, are you ready? If you’re not in contact with people and he’s not in contact with people, you might consider both getting Covid tests, and set a date for the day after your test results come in. It’s not perfect, but it might be a workable answer if your standards align. If you’re both negative, you could meet face-to-face. And since you’ve spent so much time on the phone, and Covid is weird, and we all have no social life right now, make a real date of it. A picnic lunch and a walk around an urban lake or park — something that would actually be fun in these dark and uncertain times.

Good luck!

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Wendy Newman is the author of 121 First Dates. She’s a dating, sex, and relationship expert who’s led hundreds of workshops and revolutionized the lives of over 70,000+ women internationally.

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