LIFESTYLE

What You Need to Know About Getting Back in the Dating Game

Getting back into the dating game when you’re in your 40s can feel overwhelming. At this point in your life, you’re probably set in your ways, you’re really busy with your career, and there are likely kids to consider. Every potential partner has their own set of baggage, er… I mean, experiences. But I’d argue that none of this is a bad thing. In fact, if you’re getting back into the dating scene in your 40s or up, you’re guaranteed to be wiser, better at knowing what you want (and what you don’t), and a lot less impulsive. So, whether you’re single for the first time in a long time, or you just haven’t met the right person yet, let these 10 tips inspire you.

dating over 40, couple having a romantic outdoor lunch on a sunny day with wine

#1 | Make Sure You’re Ready to Date

Too often women over 40 rush back into dating because they are afraid to be alone. They’ve grown accustomed to being in a relationship. In other cases, women feel pressured to jump into the dating scene prematurely by well-meaning friends or family. Monte Drenner, a licensed marriage counselor and coach says, “I always encourage clients to make sure they have healed from the wounds of previous relationships prior to pursuing another one.” So basically, it’s ok to be single. It’s ok to take some time to be alone. Get comfortable being alone, and then decide what it is that you really want out of your next relationship. By getting clear about who you are and what you want, it will be easier to navigate the dating scene.

#2 | Be Positive

Start by being real with yourself. Accept that there will be good dates and bad dates. The positive spin is that every bad date will bring you one step closer to a good one. I have a good friend who complained to me after her divorce that “all the guys I go out with want younger women.” I gently suggested to her that her broad stroke of cynicism is only working against her. Although I’m not a relationships expert, after years of watching Deepak Chopra and Wayne Dyer on PBS, I suggested she change her mindset from “dating is scary and difficult” to “dating is fun and easy.” Positive people attract each other—and if I retained anything from Chopra and Dyer, it’s that the Law of Attraction is real. Read Erin’s own experiences with the power of positive thinking here.

#3 | Know Your Deal Breakers

What you were willing to tolerate in your 20s and 30s might be very different than what you’re willing to today. Yes, you have to be flexible getting back into the dating scene. But it’s easier to date more productively when you know what your deal breakers are. For example, if you don’t want to date someone who has younger children, you’ll save yourself loads of time by simply saying no to anyone who is running around to soccer and ballet practice every other week. The same goes for money, religion, and lifestyle. If you’re not the church-going type, don’t date a preacher. It’s not about being judgmental, it’s about setting up successful dating parameters. Chances are you’re much better at knowing what you want now that you’re over 40, so stay attuned to your needs. It’s the best way to create self-confidence.

dating over 40, happy stylish couple over 40 walking arm in arm down a city street

#4 | Don’t Get Hung Up on a “Type”

We all have a “type” that automatically attracts us. But to find a quality partner, it’s time to set those expectations aside. I recently spoke to a childhood friend of mine in preparation for this blog. She’s in a growing relationship with someone who is completely different from anyone she would have ever dated when she was younger. She had come to the realization after her divorce, that dating her “type” would most likely land her right back to the dynamic that didn’t end well. So, she took a chance on her opposite, and it was the right move. That isn’t to say that you should settle. Do hold out for someone who you really enjoy spending time with, but be open to something different. Bonus tip: Don’t compare! Try to get to know the person in front of you instead of comparing them to the person in your past.

#5 | Be Real on Dating Apps

Going into your fifth decade (or more) don’t post a picture of yourself from 20 years ago. Your date is going to show up expecting to see that person, not the woman you are today. Embrace your wrinkles, gray hair, and body weight, and accept yourself. It’s important to be okay with who you are now. When you own who you are, you’ll be in a much better place to be in a truthful, open, honest relationship. On the flip side, skip the current bikini shot. You may be a fitness fanatic and have a great body, but your attempt to show that you’re hot in your 40s is not the best way to be taken seriously.

#6 | Don’t Take It Personally

Dating can require thick skin, so start developing it now. Remind yourself that nothing a stranger does is really about you. A girlfriend of mine once said to me, “How can I not take it personally? We went out and he didn’t call. It’s personal.” If you’re like most people, your mind finds a way to make it about you. When someone rejects you, however, they’re basing that rejection off their own preferences and values, which you may or may not even agree with. Think of dating like a chemistry experiment. Just because two chemicals don’t produce sparks when you put them in the same dish, doesn’t mean something’s wrong with one of them. I know it’s a cliché, but “it’s not you, it’s me” is sometimes just that. Maybe they’re afraid of commitment or they’re into someone else. Sometimes it really has nothing to do with you.

dating over 40, happy couple having coffee in a café and laughing

#7 | Don’t Trash Your Ex

“It’s a big turn-off and it shows you haven’t moved beyond that relationship,” says Elliott Katz, author of Being the Strong Man a Woman Wants: Timeless Wisdom on Being a Man. Your ex or custody battle may be a large part of your life at the moment, but it’s best to not let it control your conversation on your first few dates. Think about it—would you want to hear your date trash their ex over dinner? These stories don’t make good conversation starters, they suck the energy out of the date. You want your date to learn about you and what makes you great, and you want to find out about them. Bonus tip #2: Don’t always make your conversations all about your kids. Men want to know you have a life outside of motherhood, which will hopefully include them.

#8 | Meet His Family and Friends

Seeing how someone interacts with his friends and his family will tell you a lot about who he is as a person. And, with so many dating scams out there and people pretending to be who they are not, this is a great way to see for yourself that the person you’re dating is authentic. I’m not saying you have to meet his people right away, but if you’ve gotten past the first few dates, it’ll give you a lot of insight. If you’re still at the meeting online stage, be sure to spend several weeks getting to know them first through emails and video chats. Someone I do business with actually does background checks to ensure they have no criminal history and aren’t already married before she invites them to meet her kids.

#9 | Be Open to Unconventional Families

A big part of dating over 40 is accepting different family scenarios such as co-parenting. This requires a little flexibility as you work around “I have the kids this weekend” or actually going on dates with the kids. My friend gets frustrated in these scenarios because it dampens their ability to be spontaneous. I’ve had to remind my friend that her daughter is almost in college, while his son still requires supervision. Another thing to be open to is when your date is still friends with his ex. Rather than feeling threatened, take it as a level of emotional maturity. It could be a sign that he understands the things that are most important in life and doesn’t dwell on anger.

Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing a black puff sleeve blouse by IRO, ripped skinny jeans by Rag & Bone, Schutz black croc-embossed knee high boots, Chanel boy bag, and Topshop belt in Telluride, Colorado, dating over 40 Date Night Outfits, Fashion blogger Erin Busbee of BusbeeStyle.com wearing black minimally distressed jeans, Jimmy Choo pumps, and faux leather one shoulder top by Nanushka in Telluride, Colorado, dating over 40

#10 | Get a Dating Look

A great way to boost your confidence is through your wardrobe. Whether it’s a classic LBD, a slimming jumpsuit, or some stylish jeans and a great top—whatever it is, have a go-to outfit that’s comfortable and makes you feel great. Make sure you feel like you are your most confident self in whatever you choose. Not sure where to start? Check out these videos with Erin’s pro tips to help inspire you. For details on the outfits above, check out this post with info on what to wear when you haven’t dated in years…Including 1st, 2nd, and 3rd date outfit ideas!

Do you have some personal dating advice you’d like to encourage us with? Please share in the comments below!

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Thank you for reading!

Amit Bloom
Amit is a loyal subscriber turned contributor from Miami, where she founded and edited an award-winning lifestyle magazine for over 20 years. The loves of her life are her husband and their two fiercely independent and creative kids. She has been known, however, to proclaim that her favorite child is their Shiba Inu, Zac.
Join the Conversation

7 thoughts on “What You Need to Know About Getting Back in the Dating Game

    1. Yes, COVID has upended all our lives. Meeting people virtually, while not ideal, is probably the safest option right now. Let’s hope things will improve soon so that you can get back out there!

  1. I would add that it is important to be wary of scammers on dating apps. My experience has been that there are a lot of scammers and fake profiles out there and I have yet to go on a date, even before COVID. Same thing with Facebook’s dating app. Be especially wary of men who say they work in the offshore petroleum indsutry. I exchanged messages with one for over a month – he said he was on an oil rig in the Mediterranean. Long story short he ended up asking me for $19K. I didn’t give it to him, blocked him on WhatsApp, and reported the interaction to the FTC. It may sound crazy, but a lot of women are too trusting and get sucked in. I think scammers prey on older women because they assume that they are a) lonely, b) likely to have more money since they may have been working for longer.

    1. Thank you, Lynn, for bringing up this very real and terrible scam. I’m sorry that this happened to you, but am so glad that you were smart enough to recognize what was going on. Unfortunately, it’s a sad reality of our digital world and women should most certainly educate themselves. Wishing you all the best of success for 2021!

      1. Thank you for your well wishes. I am not worrying too much about dating right now and am using the pandemic isolation to take some online classes for a paralegal program.

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