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Fabulous Over 40: Dating For Grown Ups

Dating today is a whole new beast...

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Dating today is a whole new beast. No matter your age, you have likely encountered challenges.

But what about the 40+ singleton who remembers the Ghost of Dating Past (where some of us wish to return to)? Before apps, iPhones, Tinder and dating profiles…before Myspace and Facebook changed the face of what “social” meant forever?

We asked our matchmakers to address this demographic of daters, our fabulous 40+ readers…

Brigitte Weil, Tawkify Matchmaker, Author of Eat Date Love, Chef & Founder of I Hate Celery Sticks:

True Story: on Day #1 as a Matchmaker for Tawkify, my very first client met me over coffee, sat down across from me and loudly said with relief, “Phew! I’m so glad you’re not some young 20 something!” 

Hmm…I think it was a compliment, but it left me wondering if I should have opted for the botox instead of my new bangs after all…

I may be partial to this topic but here’s the truth: I am 100, no, 1000% better at everything in life today at 51 than when I was 21. 

Especially dating. 

Here’s why: As we age, we get smarter, more insightful, wiser, and more confident about what makes us happy. Our twenties and thirties are the learning years – full of mistakes, questionable choices, and sometimes regret. That’s ok – this is wonderful and useful intel. If we’re open and honest, we’re starting to learn how to make better, more loving choices for ourselves.

As we enter our 40s and 50s, we get to actually use all of our accumulated experiences from the past two decades to our advantage to create the very best happy versions of ourselves today.

Our history becomes our compass to true happiness and meaningful relationships. 

Here are my 4 top tips for getting into the dating scene post 40:

  1. Shift your mindset. Don’t think of dating as looking for the “One.” Use dating as an opportunity to re-discover yourself, and what is important to you. What mattered at 20 is not what concerns us at 50. It’s normal if you’re not exactly sure of what you like or want. Going out on dates is your telescope into how you want to navigate the future and what is meaningful and makes you happy.  
  2. Go on 10 dates before you declare what your deal breakers are. Go out with different kinds of people and explore. This is how you’ll become more aware of what you like and dislike. Get out there! Have fun! Consider dating as an opportunity to discover what you truly desire. Just like with anything new, you get better at dating the more you do it. You just need to start. 
  3. For the dates where romantic sparks don’t fire, don’t call it quits. Exchange numbers, become friends, become dating accountability partners, use your date as an opportunity to make new friends and create new relationships. My best guy friends today evolved out of yesterday’s dates. 
  4. Be patient. It’s not a race. The important take-aways are in the journey, not the destination. Embrace and relish this time. (You won’t regret it, promise. I know. Remember? I’m not a 20 something).   

Dionna Smith, Tawkify Matchmaker:

As a Matchmaker, I work mostly with clients in their 40s and 50s. I am 41 and recently divorced, so this topic is right up my alley. In my personal life, I enjoy coaching my fellow 40-something friends who have either never been married or are also recently divorced. This is what I remind my friends and clients…

  1. Be open-minded: By the time we are in our 40s and 50s we have become a lot more sure of who we are. We can be pretty settled in our ways and often “know” what we want. That’s actually a great thing and one of the things that women/men love about men/women in this age range.

    However, don’t be too rigid.

    Don’t rule people out before you get to know them. Another beautiful part about this time in life is that though you are confident in who you are, you are also still evolving and have so much more life to enjoy. Be open to new adventures and new people. 

  2. Embrace the beauty of aging: I frequently get feedback from men in their 40s/50s that 40/50 year old women are either very confident at this age or very insecure about their aging bodies (this can certainly apply to men as well, but I will expand from a female perspective). Sometimes a woman will put herself down or compare herself to younger women by pointing out her “perceived flaws” while on a date. This type of behavior may not come from a negative place. Perhaps it springs up due to nervous energy (or even an attempt at humor) — but it’s best to stay positive while casually dating. A certain level of insecurity is natural and perfectly normal, but overtly declaring those insecurities is not advisable.

    The best way to get rid of nervous energy that may lead to situations like this is to spend a little more time in the self-love department. Don’t put so much pressure on yourself during the date, just enjoy it! Go into your date with the expectation of simply meeting someone new and having a good time. Which brings me to my next tip… 

  3. Keep it light on a first date: As we enter into our 40s/50s our filters begin to disappear. We’re generally more straight-forward and comfortable with telling others exactly what’s on our minds. This is fantastic and can be wonderfully freeing, but all things must be in balance. Example: If your goal is to be married in the next 6 months, throwing that out there on the first date could scare the heck out of an otherwise interested date. Remember, you are being open-minded and enjoying the journey.

    If you aren’t a fan of bowties and your date is wearing one, telling him how much you despise men in bowties is just unnecessary.  

  4. Be Positive: Peace and positivity is an essential element of life. Negativity and drama are exhausting, and not conducive to the development of a healthy relationship. At this age many of us have children, high pressure jobs, and are often juggling A LOT. 

The relationships we ultimately decide to invest in should be a refuge from the other pressures of life.

After dates that I plan for clients, I almost always get feedback on the other person’s energy: “She had great energy.” “He was so positive and fun!” OR the exact opposite: “There was something about his energy that I just couldn’t connect with.” “She seemed to have a negative outlook on life.”

Don’t use your limited time on a date to complain about your ex, exchange online dating horror stories or divulge how much you hate dating and think you’ll never find anyone. Instead, focus on the fact that your paths have crossed and you have a chance to get to know each other. 

What if you are just a naturally pessimistic person..? I am not saying to not be yourself. I am suggesting that you allow this time in your life to be an opportunity for you to grow in this arena. A simple way to do this is to practice. Think about a few topics that you do feel optimistic about… and be purposeful in leading your conversations in those directions. If you find yourself talking about things and people you hate, practice stopping yourself and redirecting to one of your “positive topics.” 

5. Most importantly, RELAX! Date with the intent of meeting new people and having fun. Far too often I hear from 40+ singles that their dates are too intense and want to move too fast. The goal of your first few dates with a new person should be to enjoy the date and decide whether or not you’d like to see the person again — That’s IT!

So have fun, be in the moment, joke around and casually get to know each other. Don’t use the first date as your opportunity to grill your date while you mentally check off your potential wife/husband checklist.  

NO one wants to feel interrogated…. especially by someone they just met.

Your 40s/50s/60s are often the BEST time of your life, and along with all the other wonderful things about being in this age range, you get to enjoy the excitement of meeting new people and dating. Have fun and enjoy the journey!  

Dorothy Stover, Tawkify Matchmaker, Author of Amazing Love Diet and soon to be released, War On Love:

Life begins after 40…Really 50! 

This is the time of life where people usually feel more comfortable in their own skin and have confidence in who they are (which just so happens to be what most people say they are attracted to). If someone over 40 has these qualities plus they can have fun and laugh at themselves, they will attract a great partner! 

Dating at any age is challenging. People can get caught up in the what-ifs or the not-good-enoughs. What we are most likely looking for is connection with another human being. Everyone has a story and once you know that story, it’s easy to fall in love with someone. Certainly never settle, but be open to hearing someone’s story and then sharing your own. That gets you one step closer to authentic love. 

Donna Swope, Tawkify Matchmaker:

As a woman in this particular demographic (yup, I’m 53)… I will share my principle dating rule for singles 40 and up…

Donna’s Rule: Don’t date what you can already deliver.

Stop playing it safe. Date people who can offer you adventure, a fresh perspective, and FUN!

Being a bystander in your own life due to fear is no way to live. You’ve likely been hurt, gone through a divorce and/or had terrible dating experiences. I get that, and odds are whoever is sitting across from you at your next date has been there too (matchmaker note: that doesn’t mean you should blow the whistle on all of your relationship horror stories on a first date though — don’t!). The point is, we all come from previous relationships and carry some baggage, so let it go.

The past does not dictate your future.  

View dating as an opportunity to move into a new and exciting phase of life. This is a time of growth and self-exploration. You aren’t the same person you were in your 20s, so ask yourself: who are you TODAY? What are you looking for in a partner TODAY? Knowing who you are and what you want is essential. Just as important, is identifying what no longer serves you and what behaviors you prefer not to bring to new relationships.

The crux of all this: Take risks. Be authentic. Be vulnerable.

Show up for your dates as the real you and not who you think you should be (because eventually you will have to take down the facade). Besides, it’s exhausting to keep up the charade of trying to be everything to every man/woman you meet. So…don’t. 

Share your interests. Ask questions to get to know them. Learn about their family, retirement plans, career, music, hobbies. Find those commonalities that you can build off of. They will become the foundation of any healthy relationship. 

Be mindful that everyone in their 40s, 50s and 60s have already built full lives.

We have family obligations, careers in full-swing, children to care for (maybe), lifelong friendships, etc… Finding spare time may be a challenge, so look for ways to creatively make time for dating (lunch and/or coffee dates, anyone?).

Focus on QUALITY not quantity.

Perhaps, most essential… listen to your gut. Trust yourself. If things feel good, go with it. If something doesn’t feel quite right, then back away. Your seasoned instincts are probably right.

Sophy Singer, Tawkify Matchmaker, offers advice for the “soulmate” searchers: 

This is advice I give to all my clients (regardless of age): If your end goal is to find your life-partner/husband/wife/soulmate/whatever-you-want-to-call-it, then the dating process should be viewed as a means to an end. It’s a numbers game!

The more people you meet (with an open-mind and open-heart), the higher the chances are that you will hit the love jackpot. So many things have to be aligned for two people to meet and fall in love. It’s a combination of connection, timing, and that elusive stroke of luck. All three components have to be there for two people to click. 

Allow yourself as many opportunities as possible, for the stars to align for you! Stay focused on the goal. It’s work, and it can be tough, but the final reward is so sweet, that every crappy date was worth it. I can personally attest to this! Now is your time. You know what you’re looking for (at least you think you do). You can be picky. You can be selective… But, only once you’ve met someone. Take every opportunity to get in front of someone new. You never know what lies around the corner, just beyond what you can see right now. Love arrives when you’re fully open. 


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