If My Date Has Anxiety, Is That a Red Flag?

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Hey Wendy,

I’ve just discovered your book and can’t wait to read it!

I am confused and hurt by a recent breakup and wanted to get your opinion on what happened. I dated a guy for about a month. In the month we got to know each other, he seemed like everything I could want in a guy. He was kind, easy to talk to, a gentleman, offered to pay on every date (I swooped the check sometimes though), and I felt like our connection was growing stronger with each date.

Because he’d done so much for me, I bought us tickets to see his favorite musician who he’s never seen live before. I was so excited to do this for him and knew we would have a blast. When I got to his house to pick him up for the date he told me he couldn’t go to the concert and he couldn’t date me anymore.

He said he was going through personal stuff and his anxiety was getting to him. He missed where he used to live (he moved from North Carolina to the California Bay Area) and only had $2 in his bank account. He said he had an amazing time with me and then he goes back to feeling unhappy so he decided to end it. I still feel hurt and confused by it all. He had talked about how he has anxiety sometimes but never showed signs of it and seemed to have it under control. And well, living in the Bay Area, we all are tight on money so I never considered these things as red flags.

I just don’t get how all was so perfect and then ended so abruptly, especially right before a concert! I would love your insight on this situation. Is anxiety a red flag when getting to know someone?

If someone is unhappy with an aspect of their life (job, money, etc.) is that a red flag?

Thank you, Wendy!

Jennifer B.


Hey Jennifer!

I’m sorry this experience has left you hurt and confused!

I hate it when the start of something feels so perfect and promising, and then poof! They’re gone before it even had a chance—super disappointing and confusing. But you did nothing wrong.

How someone is affected by anxiety, depression, or other mental health issues differs from person to person, and mileage will vary in individual experiences; you just can’t evaluate a relative stranger for signs and symptoms and then know whether or not they’ll flake on you because of what they’re struggling with.

In light of this, I wouldn’t say it’s a red flag.

It’s more like a Post-it note you stick on your fridge—something you check on from time to time during the “getting to know you and what I can count on you for” process, which, in my opinion, takes about a year.

Your actual connection with potential partners is also going to vary from person to person, and it sounds like this was a strong one. The strong ones are rare, and they can feel perfect. You want to be gentle with yourself and take a minute to grieve this loss. Hide under the covers, binge a show on Netflix, eat ice cream, reach out to friends, hit the gym or hiking trail to work off the ice cream, then shake it all off and start again.

Back to timing: At one month, you can’t expect yourself to be able to make accurate evaluations on his character—anxiety or no—as you didn’t yet have enough information about him.

This is all that “dating” is: Hanging out with someone over and over so you can determine how they handle life, and whether their style syncs with yours. You’ll learn how they handle their circumstances, and the curve balls life throws. How do they navigate their own limitations? When they get stuck, how do they break through? And do they have the bandwidth and aptitude to handle all of who you are? This stuff takes time, so don’t get down on yourself for not seeing the signs earlier with this one.

So, this guy has self-selected out. My prediction is he’ll circle back around at some point, and when he does, I beg of you—please be willing to look beyond that delicious, romantic energy you’ve felt for him and see the whole picture. Evaluate his capacities, limitations, and circumstances with a discerning eye. In other words, enter at your own risk and go in with eyes wide open, because he’s already demonstrated what he can be counted on for (bailing when the pressure is too great). Can he also be counted on to recognize that impulse in himself and change? We don’t know yet. Ultimately, you want the one who can’t believe he finally met you and has the capacity to do what it takes to keep you in his life—that’s your guy right there.

Good luck and happy dating.

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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.

Need one-on-one help from Wendy? You can hire her by the hour.

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