Online Dating: The 6 Things Every Woman Needs To Think About First

Welcome to the sisterhood of the newly single middle-aged woman. Since there are so many of us here navigating new but somewhat familiar waters, I want to help you benefit from my experience with online dating.

We are dating again. Or as I look at it, “Holy Cow! I get to date again.” (Yes, I am very much enjoying this adventure more than you can imagine but those stories will have to be saved for another time).

6 tips for women with online dating

After many years of marriage, which may have been focused on raising children, building careers or just trying to make an unsuccessful marriage work, we are now thrown out into the world of dating circa 2017. No longer do we have to wait for a friend to set us up or hope to have the good fortune to run into some fantastic person in the produce section of the supermarket. We can make our own destiny!

[Read Next: Empty Nest: When the Kids Leave Home, Who is the ME Left Behind?]


You are single right now.
You are interested in meeting someone new.
You have all the tools you need in your hand at this very moment.

Before you go forth (and take precautions not to multiply), here are some tips I have learned on my journey through the land of Match, Bumble, JSwipe and a handful of other sites. These tips will help you get started and give you courage to take the first step.

Six Tips for Women for Online Dating


Current and accurate pictures are important. Of course you love that old picture from your trip to San Francisco, the day your skinny jeans zipped easily because you were getting over a stomach virus. I especially love the one from the day ten years ago when my hair was blown out for a black tie event and I felt like a starlet. However, I do want my date to recognize me when we meet the first time in person at Starbucks for our afternoon latte. Wouldn’t you rather someone think you look better in person rather than be disappointed with the real life version. Definitely use flattering photos but make sure they are a fair representation of what you look like in person.

Ask a few friends you trust for input or even for help taking some new pictures. Be mindful of what you are posting because it is the first impression you are giving. However, don’t overthink it. Just be real and make sure the pictures you post give someone a true glimpse of who you are. There is someone out there in the universe (hopefully in the same time zone not just the same universe) who will appreciate you completely. You don’t need to pretend to look different than you do in real life in order to find the right partner for you which leads to my next important point.


Are you looking for a long-term relationship right now? Or, have you acknowledged that in 2017 women are allowed (and encouraged) to have their own sexual needs? The right answer is the one that is the truth. If you are ready to meet your “person”, then say that. If your goal is to meet men who are interesting and fun that you can go out to dinner with and possibly also have breakfast with the next morning, then don’t pretend you are searching for your life partner when writing your bio.

This is the time of life to get in touch with what you want and go after it. Write in an honest and kind manner of course. However, state what you like in a positive way. For instance, I have discovered I very much enjoy tall intelligent men with a great sense of humor. I have a close friend who is turned on by bald men who are outdoorsy and love to read. Neither one of us is wrong and neither one of us is offending those who don’t fit our desires. However, those men who identify with specific characteristics will feel drawn to someone they know is looking for them.


Be open-minded when swiping. Unless someone fits into your deal breaker category, give him a chance and have a conversation. Don’t assume someone isn’t a match based on an unflattering picture or a typo in a profile.Yes, I know women who will swipe left if they don’t like someone’s shirt or the way a man wears his baseball hat in a picture. You could be missing out on a great person just because their fashion sense is different from yours.


Even if you don’t know someone’s last name, you can find him on social media. Enter a phone number into the search field on Facebook and most of the time, a person’s profile will be linked to their phone number. Take a look at your match’s public Facebook page. You can learn quite a bit about someone with a quick glance at his social media profile. Unfortunately, you might discover a man is married or in a committed relationship even when he is claiming to be single, which leads me to my next point.


(AKA Think the way your neurotic mother wants you to think.)

  • Once you match with someone, you will go through the typical steps. First, you will chat on the site.
  • Then you may want to text a bit or immediately speak on the phone.
  • Be aware / Listen to your gut. If something doesn’t feel right or more importantly, doesn’t feel safe, listen to your inner voice. If a man only wants to text and never talk (especially at night), that could be a sign he is not free to talk because he is indeed in a relationship with someone and she is in the bed next to him. Don’t laugh; I had that exact situation happen.
  • Make sure you meet somewhere safe and public.
  • Let a friend know where you will be. This is an exciting, fun adventure but you still need to remember you are meeting someone in person who you know very little about. I send a picture of my date to a good friend, let her know where we are meeting and I give her his phone number as well.

[Read Next: After My Divorce, Here is What My Future Won’t Be]


You are lucky enough to be getting a do over! This is your chance to meet the person who fits who you are as a fully formed adult. When you dated in your twenties or early thirties, you were very different than the woman you have created over the past decade(s). You, like me, were probably not completely confident in your own skin. Now, you are a strong woman who has been through the fire and come out the other side. I had an incredibly amicable divorce and I still had pain and it was still difficult. I am proud of who I have become and I want you to be proud of yourself as well. You have traveled a long hard road so embrace and celebrate the woman you are now and honor her by representing her honestly and completely.

Be Yourself! Really!

Recently, a man, who of course is tall intelligent and funny, asked me if I ever say anything that I reflect on later and ask myself, “Why did I say that out loud?” He meant it in a playful and endearing way so I was not offended at all. I thought about it for a moment before I answered.
I then answered confidently, “Actually NO!” I used to feel that way. I used to worry that if I said what I really wanted to say, someone might not like me so I had to make sure to present myself in the way I felt people expected (wanted) me to be. I have since come to terms with who I am and I am definitely a different flavor than most. I decided that I would rather be honest about who I am from the beginning. That way, if I am not for you we will know right away.

I encourage you to take some time to determine your own individual flavor, to embrace who you are and to create your profile with your very own voice!

Be real. Be safe. But, most importantly, have fun!

Just in case you are wondering, yes, I did see that man again. I just may be the right flavor for him. If not, I will still be happy that I had the experience of meeting someone interesting and I will move on knowing there is someone out there who will think I am delicious!


At Midlife Why I Would Never Want to Be 30 Again 

When Parents Are Divorced, How to Make Parents Weekend Work 

Terrifying Things About Returning to Work And Why You Should Not Be Scared 

Don't miss out!
Want more like this? Get updates straight to your inbox.