Today’s topic is one I haven’t ventured into before, but I thought it would be an interesting one to bring up and chat about with y’all. I know I’m not the only woman who has ended up in her 50’s and dating again. It’s not the best place to be, but it is better than being miserable, I’ll tell you that.
If you’re someone who got it right the first time and married the man of your dreams, had children, and now are enjoying your older years with the love of your life and grandchildren, well….you are blessed indeed! That would have been my dream come true too. You can count your blessings right now that you’re not still out there, but you might get a kick out of reading this anyway. Getting it right the first time was not the way life happened for me and I imagine for many of you as well. I didn’t get the results of what I expected to get earlier in my life and life doesn’t always turn out the way we hope, dream, and plan. I made plenty of bad choices along the way and it didn’t go the way I wanted it to go, but the blessings aren’t over yet, nor is life over yet.
Growing up and starting to date, I had the same dreams as most all my girlfriends. I wanted to fall in love, get married, and have kids. My life didn’t turn out the way I thought it would and I had NO idea that I would end up in my 50’s, single and dating again. Dating in my 50’s is a whole different story than when I was younger in my 20’s and dating, as I’m sure my other single 50’s friends will agree. It’s a whole new ball game, some good and some not so great. Men in their 50’s and 60’s can still act like little boys and it sometimes feels like we are all in high school again, even though our ages tell a different story.
Things are so different now that online dating has completely taken over as the main way to connect and meet eligible single men, so that is what I’ve done while single in the last few years. I first did online dating in the early 2000’s and then again 3 years ago. I think more relationships than ever start online these days! It’s a process and you just have to do your homework no matter how you meet men, but it can certainly work.
It worked for me, I’m happy to say! I met my boyfriend on eHarmony, just to let you know. I’m not going to get into all the particulars of my new relationship, but will share more of my personal life along the way as life unfolds. For now, I’ll tell you that we are very, very happy together and have a great relationship. We have met each other’s families and all of that went well.
Today’s post will be about dating in your 50’s and I’ll share my experience with it, since I’m sure there are many of you who are single and want to get out there dating again. In fact, I’ve had plenty of emails from readers out there asking me to write about dating in older years, so I know it’s something of interest to a lot of you. I’ve heard from so many of you over the last 5 years since my divorce who had similar situations to mine. Divorce is painful and can be devastating as mine was for me, but it’s not the end of the world. Trusting again can be difficult after being in a deceitful relationship such as I was in and I know others have experienced that too, but life goes on after divorce and can be even happier than you can ever imagine. I’ve been very happy and content the last 5 years, but still didn’t want to be alone forever.

Single girls unite
I have several single girlfriends that I have hung out with the last 5 years since my divorce and it’s so nice to have other friends who are in the same situation to talk things over with. They understand what it’s like to date at this age and try to find a good relationship out there. Some of them want to find someone to settle down with and some of them do not. It’s not that easy, but it is totally possible to find someone! But, you have to really want it to go after it and put up with the angst that comes with dating again. Opening up, trusting, and getting to know someone is part of the process.
As we get older, the traditional ways of meeting a mate get harder and harder to find. Meeting in college, at work, through friends, or at church have been the normal ways of meeting people, but as we get older, those methods are less and less effective, so that’s why online dating has become so prevalent. Online dating is for all ages now, younger to older and there are plenty of single folks out there at this age too. We just have to be careful in the process.
Given all that I’ve been through in life, I’m much more careful with how I approach dating now and as I’ve dated the last 3 years, I looked at all my dates as getting out there and being social and didn’t necessarily think they would all turn into something serious. You have to have an open heart and mind when dating at this age. There’s not a lot of room for bitterness and you have to get past that. I needed time to myself and to heal, so I didn’t jump out there fast. I’d say the best way to prepare yourself for dating at this age is to take the time to get to know yourself and what you are looking for. I definitely knew what I didn’t want and that helped me to know what I DO want in a relationship. We’ve all been through junk in life by this age and some of that gets carried over into a new relationship, so you have to look at all of them as they are right now, at this stage in life.

My single girlfriends and I
I waited until I was divorced for 2 years before I got back out there again, so it’s been 3 years ago that I started online dating. I joined Match and also eHarmony and have been off and on both of those online dating sites over the last 3 years. I’m happy to say I’m not on any of them now. 🙂
I’ll talk a little about both. eHarmony seems to cater to Christians and it definitely matches people up based on faith preferences. They make you fill out a really long questionnaire about yourself, which is a bit tedious, but once you’re finished with that, it’s not so bad. The thing I don’t like about eHarmony is that they go through a series of getting to know you multiple choice questions. If someone is interested, they send an ice breaker with questions and you answer back and ask them questions too. You can choose pre-written eHarmony questions or ask your own. Those are sort of trite and I don’t feel like you really get to know someone until you get to the real emails. You can also jump straight to emails at anytime too, which I preferred on that site. I didn’t like that eHarmony matches you with men out of state, even though I put in my profile that I was only interested in local Atlanta area men. I had to email more than one to tell him that I wasn’t interested in an out of state relationship.
Match is probably the biggest online dating site with millions of users. There are lots of men on there in the older age group and again, you just have to do your homework. It can be like a smorgasbord to men with all the pictures and profiles and there can be lots of back and forth communication without it going anywhere. I tried to screen men on Match too and stated my faith preferences right on my profile to try to qualify someone in the beginning without wasting time on those I knew wouldn’t work for me, since shared faith is very important to me.
You have to approach dating sort of like looking for a job. Each first date is like a job interview with both parties getting to know each other to explore and see if there might be a 2nd date. That can be nerve wracking, but if you approach it with a fun attitude in mind, it’s not so bad. Not every 1st date will lead to a 2nd date and that’s OK too. Not everyone will be a match, but you are looking for that ONE special person out there. I think you can tell a lot about someone on the first date, so talking and getting to know them is the first step.
My method of dating was to not get into too much about the past on the 1st date, or even the 2nd. You need to give yourself time to have fun and get to know someone on the surface, before you dive into the serious side of things, i.e. past relationships/divorces. Keep things light on the first few dates and have fun. You can still get to know someone and not have to know everything about them right off the bat. Ask questions, but keep it light. No one wants to feel like they are being interrogated, but that’s what dating can feel like sometimes.
It’s funny, but even in a city as big as Atlanta, there are large amounts of single people in my age group of 50’s and 60’s, but it’s actually a smaller group than you’d think. Several of my single girlfriends and I have been on the dating sites at the same time and ran into the same men. We had to compare names and notes along the way to be sure we knew what was happening with each other and more than once, we went out or had contact with the same guys. We just had to laugh about it! It’s going to happen in most cities, I would imagine.
You’ll meet all sorts of men when you get into online dating. I had a slew of older men, at least 8 to 10 years older who contacted me. I’m sorry, but that’s just too old for me and I didn’t respond to most of them. Men in general still want to date younger women, no matter what their age and I guess it’s still working for them, but that much of an age gap was too much for me. I wanted someone closer to my own age. Some of them lie about their height and age and post pics that are much younger than they really are. I’ve heard the same about women online too, so I know it’s not gender specific. I’ve compared notes with many of my single girlfriends about what and who they are meeting out there. Finding a good one is like looking for a needle in a haystack, it seems!
I also joined Meet Up singles groups and those are a good way to get out and be social again. I met up with my girlfriends and we would go to dances or restaurants or shows of some kind and it was a good way to get out and socialize with other singles in our age group. That method didn’t really help me meet anyone I wanted to date all that often, but it’s still an option to stay social and busy. We laughed that it seemed the same people showed up at events all the time and we felt like it was just a revolving door of the same men over and over. I think most cities have Meet Ups now, so check out the website, meetup.com and see what’s available in your city if you want to get out and be social with this age group.
When you get out there and date, you’ll meet all types of men and you just have to do your homework and keep an open mind. By this age, there can be quite a bit of baggage, so you just have to decide what you can live with (or not). All you have to go by on profiles are the pictures and written text and some of those pics were really bad and some look really old. Hard not to judge by looks, but I tried to keep an open mind on that too. I met men who were my age and had teen age children, or younger. That wasn’t something I wanted to sign up for, so I knew that wouldn’t work for me. You also have to look at finances and make sure someone is stable at this age. I didn’t want someone to support and take care of. Nope, that’s not gonna happen. I was looking for an equal partner in life who had his act together as much as I do now. There is not going to be any perfect scenario at this age, so you have to find the best fit for yourself all the way around.
I think chemistry is important even now and that has to be there too. I met a lot of different men and some didn’t match up in faith, financial stability, or chemistry, so you do have to decide all the things that come together and make a special relationship for yourself. I wasn’t willing to settle for mediocre just to have someone. I really wanted to find true love this time around and find someone to share the rest of life with and who treats me like a treasure. Family is also very important to me and I needed someone who also has that in common, a love and priority of family. Not everyone is close to their family, but I need to have that in a relationship with someone who also gets the importance of family.
Women can sometimes be very gullible. I’ve heard that over and over again and some of you have even emailed me about trust issues. We want to believe the best in a person and that means closing our eyes to things we see at times. I’d say that you have to be open hearted, but also be smart and diligent about dating at this age. There are men out there who will take advantage of women, we hear those stories all the time and I’ve lived through and survived my own nightmare of that scenario. So, my caution is to listen to your gut and follow your instincts while dating. Most of the time, you can see the red flags and cautionary signs if you look closely for them. They are there if you’re looking.
So, that’s how I approached dating at this age and time in my life. How about y’all, if you’re single and older? Are you interested in dating again or have you thrown in the towel like some of my friends? It’s a gamble to get out there again, but I just wasn’t willing to give up on love. It means too much to me and I have always wanted to love and be loved and accepted for who I am. Some of my married friends say that if anything happens to their husbands, they will never get married again! I can understand that too, but being alone wasn’t something I ever wanted. Things just don’t always work out the way you plan them, but thank goodness for do overs!
Here are a few tips from me for online dating:
*Put your best foot forward when compiling an online profile. Be honest and open and post current pictures that are flattering.
*Have an open heart, but be cautious as well. Do NOT trust everything you hear, but put them to the test. There are plenty of players in the dating game and they are in every age group. A man’s true character will show soon enough.
*Email back and forth and don’t be afraid to share your cell #. I think talking on the phone is a good way to know if you might be interested, just by hearing their voice and how they speak and communicate. There was more than once that I just didn’t click with someone on the phone conversations at all and I was usually right if I met them in person.
*Don’t chase men. It seems that times have changed so much now in dating and that men are getting chased by women who are way more aggressive than they used to be. There are definitely less eligible men out there and more single women than men to go around, but I did not give into the chase. Men are meant to be the pursuers in a relationship and I still firmly believe that. When a man is interested, he will definitely let you know it and when he isn’t, you’ll know that too. You’ve heard about the book and the saying “he’s just not that into you”. That’s true and you’ll know it by the silence. It happens to all of us. I’ve talked to girlfriends who go out of their way to text and call men to let them know they are interested, but you really don’t have to do that. Respond positively and accept, but don’t chase!
*When you get ready to meet, meet in a public spot and you may only want to do coffee first and not dinner. Although, I did dinners too. You can play that by ear.
*Give it more than one date if you at least like someone and think you might want to see them again. You never know after just one date, but sometimes it can be good. Or you may never hear from them again. It’s a risk to put yourself out there, but you have to be willing to do it to find someone.
*Don’t take it personally if you don’t hear back from someone you enjoyed meeting. Online dating is fickle and it’s like a candy store out there. But, don’t settle and wait for the right fit.
*Don’t bring up too much baggage too soon (we all have it, just don’t need to talk about it right off the bat). There’s plenty of time for that later. Get to know each other, laugh and have fun on the first few dates.
*Just get out there and meet people and see what happens! You never know, your Prince might be right around the corner.
I hope this sparks some interest for my other over 50 readers out there who may be single and willing to try it again. It’s not easy to do this dating thing, but it’s worth it, I think to find a special someone and relationship!
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You have some great words of wisdom here, and I’m going to share them with my 20-something son! I’m happy for you and your journey.
I’m going to send this to my single friends who are dating again, it’s so well written.
I was not the least bit surprised that you did on line dating and were successful at it. After reading your blog for so long, I’ve come to expect you to be able to do anything that you put your mind to. I can’t wait for one of your how to dress over 50 segments where you have on a WONDER WOMAN outfit! LOL I love that you’ve found someone to be happy with. You have so much to offer. You have such strong faith and a wonderful family but it’s nice to also have a special someone to share your life with.
Good luck!
Rhoda,
I stumbled onto your website while I was conducting research for a similar project I’m working on. Bravo! Nicely done! I, too, am 51 and single. Married twice, each for 10+ years, I never thought I’d be single again and, to make matters worse, I’m single in a fast-paced world where technology is pretty much dominant in everything we do. I separated in 2010 and divorced in 2012. Shortly after my divorced I was encouraged by a few friends to join the online dating phenomenon. Being the traditionalist that I am, I seriously hesitated and pondered the thought for a few month before giving in. I joined match.com for about 6 months and met a few interesting and not so interesting men. Along this journey, I discovered what I wanted and quickly learned what I didn’t want. I’ve become smarter about the online dating scene and have become a better judge of character. A few men remained friends (and still are today) and others moved on in their pursuit, as did I. I’ve been stalked, met men who I like to call “stage 5 clingers” (needy men), propositioned for marriage on the second date, men who wanted to “score” on the first date, stinky men, poorly dressed men, men who brought their child to the date, men obsessed with their past ex’s, propositioned by 21-27 age rage, and even by women! I can go on to tell you funny, scary, and even sad stories, but I’ll stick to my point. I have yet to find “the one” for me because I refuse to settle for mediocre. I will press on and keep an open mind until I find him and if I don’t, I’m okay with that too. Single at 50 hasn’t been too bad thanks to social networking! Keep your heads up ladies! Dating is exhausting and disappointing a lot, but if you treat it as a social platform to meet people in general, you’re bound to find someone who will become a great friend and eventually may end up being the one for you! Also, as Rhoda said, join the meetup groups in your area, get out there and do fun things and meet others that enjoy your same passions… you never know who’ll you’ll meet! Best of luck!
HI, Bea, thank you for stopping by! I always love to hear experiences from other over 50 single women. You are so right, dating can be so disappointing and putting yourself out there again isn’t easy. But, you are also right in that I’ve learned some valuable lessons and have learned to be content with me and not settle for less than what I deserve. It’s paid off and I’m dating a wonderful man for almost a year now who treats me like I’ve always wanted to be treated. I couldn’t be happier! I hope the same for you, hang in there!
just wondering if you think some cities have more opportunities out there to meet a man in his late 50s when you’re 50 and overweight? i live in los angeles and there’s no way in this city to find a man who is not looking for the body first, age second, etc…
i’m not against retiring at 50 and relocating….any suggestions?
HI, alice, that is a tough one! I really don’t know much about other cities, since I grew up in Atlanta. I do think there are probably more men in certain cities in the older and single age group, but I just don’t know that for sure. Atlanta has plenty of single men (although I think women still outnumber men in this age bracket), but finding a quality one is the tough part. I’m very happy that I’ve found a keeper!
I was married 18 years before I was told that he wasn’t in love with me anymore. I’m trying to now get back out there. Thank You for the advice. Any good first/second date conversation starters?
Hi, Valerie, so sorry you have to go through that and starting over again. I think you just have to have a positive mindset with dating again. It can be so frustrating and yet fun at the same time. Just be yourself & see what happens out there. Don’t expect too much too soon and you might be surprised. I am happily remarried now and so glad I found a good man out there.