Dating Over 40: Halloween – Trick or Treat for Dating?

Halloween Parties for Singles

Do you dress up for Halloween? Do you even go out to celebrate this fun holiday? If your answer is “No”, you might want to rethink that.

It’s a known fact that when people don costumes, they let their guard down. Yup that’s right, people disguised as pirates, ghosts or even salt and pepper, are friendlier than usual because they give themselves permission. Why? Because their identity is hidden!

It just feels safer to be outrageous or even a little bit more dating. To take some social risks and talk to people you don’t know. And, when in costume, you make it easy for others to come up with an opening line. In essence, your costume is actually a conversation starter!

This is the same principle at work for why you are more open to meeting strangers when on vacation. Since no one knows you when you are away, you feel freer to be yourself or stretch past your normal comfort zone.

Stretching beyond your normal comfort zone is a very good thing for anyone, but particularly when you are single. The truth is, if you don’t get out of your comfort zone, you won’t meet many new folks. It’s really that simple. My dating coaching clients hear me say this all the time and you know it’s true.

That’s why I bring up the idea of Halloween – so that you can leverage this simple method to get out there, be friendly and meet new people! Never mind that Halloween is just plain fun isn’t it?

Don’t be scared off by needing the perfect costume. The simplest thing can work as well as the most outrageous, so don’t put a lot of pressure on yourself. I tell my dating coaching clients to visit one of these temporary Halloween stores – they have so much there to choose from.

If cash is tight – look around the store for ideas and get inspired. Then go home to see what your closet has to offer – or get your friends in on this adventure and look through everyone’s closet. Another good costume resource is the Goodwill or Salvation Army stores where clothing is cheap, and you are likely to find out of style items that are perfect for the look you want.

For my dating coaching clients, I recommend they find a way to get that child-like playfulness about Halloween back and to let themselves have fun with it. The more relaxed you are, the friendlier you’ll be.

Stop letting those goblins and ghouls of a “why bother” attitude or “that’s just for kids” outlook get in the way of meeting new people. Halloween parties are big with singles groups. To find one in your area, check out or Google the words “singles +Halloween+ your zip code” in quotes and see what comes up. Then put on a costume or even a simple mask and go!

Photo credit: Empirically Grounded


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

1 thought on “Dating Over 40: Halloween – Trick or Treat for Dating?”

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