My Experience with Dating After Divorce

I have been divorced and back on the dating market for 3 years now.  All I can say is, so much has changed since the last time I was single back in 2002.  Not only has our society changed so much when it comes to dating, I am now dating as a 38 year old divorced mom.  It’s a whole new world I have had to learn how to navigate.

Getting back on the dating scene after being married for 15 years has been exciting, fun and scary.  I love to have new experiences and adventures and enjoy meeting new people.  I also get scared I’m going to meet some creep with bad intentions and end up a skin suit.

I think dating can be fun if you go into it with the right approach.  Every date is an opportunity to get to know someone new from a different walk of life.  Everyone has a story.  I ask questions and hear their story, every man loves to talk about himself ;).  My personality is a huge talker, but I do my best to ask questions because I am there to get to know him.  Getting to know him is the only way I will know if I want a second date.  Even if it doesn’t go any further than a first date, it’s always an opportunity to learn something.  Something new he said about life, something new about myself, or learn more about what I want and what I don’t want.  Even a bad date is not a waste of time if I can find the lesson to be learned.

Always be safe!  I always meet my date at the restaurant.  I never let him know where I live until I feel completely comfortable and safe that he has that information.  For me, it’s at least several dates before I would let him pick me up and know where I live.  Also, to be alone in a car with a man is a vulnerable position.  This is another reason why I won’t let him pick me up until I’m comfortable.  Before a date I always let at least one person know where I’m going, what time, what I’m doing, etc.  And I check in regularly with that person throughout the date to ensure I am safe.  Always take the necessary steps to stay safe.

In the past 3 years I have been on many first dates and have had 2 relationships (one short and one long).  I have had many experiences; some good, some bad and some in between.  I plan to share specific stories of some of my dates in later posts.  There are some hysterical stories!

What do I find to be the biggest challenge?  Being in my upper 30’s it’s a unique group of men that are single.  I have found it’s either men that are divorced- which brings up all of those questions… What happened?  Do you have kids, how many, how old?  What is the coparenting relationship like?  If he talks negative about his ex-wife on the first date, run!  Then there are the men that have never been married.  Which leads to a different set of questions… Do you have commitment issues?  Are you a workaholic? Are you emotionally unavailable or have extreme mental health issues?  No one is a clean slate, myself included. 

I love the scene in ‘The Other Woman’ when Leslie Mann says: “The last time I was single the dating pool was everyone.  Now it’s a shallow puddle of age appropriate men.” LOL!!  Then Cameron Diaz goes on to say that it’s even worse than that!  This is pretty much how I have felt!

One advantage is most people my age know what they want.  They have an established life and aren’t going out on a date to waste time.  More often than not, they are up front about their life and what they are looking for.  The first date typically feels more like a job interview.  You go over all the important things and ask the hard questions.  I like this because I can make a logical decision before getting my heart invested.  Everyone has deal breakers.  You may as well ask right away and don’t waste time.

I have found it difficult to navigate dating while having young children. I am very protective over my children and always want them to feel safe.  My kids are with me the majority of the time and I don’t want to get a babysitter so I can go on a date.  I will only go on a date on nights they are with their dad.  Which doesn’t provide me a lot of free time to date.  I also keep my dating life extremely private from my kids.  I don’t tell them if I am going on a date.  They did know when I was in my longer relationship, only because they kept seeing his name pop up on my phone and they asked me about him.  They knew his name and they saw a picture of him and that’s about it.  

Still to this day my kids have never met anyone I have dated.  I tell my kids “when I meet someone who is special enough that has earned the right to meet you, that’s when you will meet him.”  And I take that very seriously.  My kids will ask me about dating once in a while.  They used to only want it to be just the 3 of us forever.  But now they have let me know they want me to meet someone and be in love.   I think as time as passed from the divorce and they are growing up, they don’t want me to live life alone.  I also think they like the idea of having a male figure in the home, it adds something that I can’t provide.  They have put in some special requests…. Caleb told me he wants a brother who is 9 or 10 years old. lol!

I spend almost all of my time with my kids, my family or working.  This doesn’t provide me much opportunity to meet someone.  This is another area I have found challenging.  Where do I meet someone?  I have tried dating apps – OMG! I could write a book on my experience on dating apps lol!  I go out with my girlfriends for dinner, drinks, music; this seems like it would be a good opportunity to meet someone.  But hasn’t ever worked out well for me.  Some advice given to me from my brother: if I’m out at a restaurant, bar, wherever and a man approaches me he’s a douche bag.  The good quality men don’t approach in this way, they usually just sit with their friends.  Which puts the ball in my court to approach him.  It’s good advice!  But it’s a hard one for me to swallow.  I believe in a man making the first move and pursuing the woman.  I can be very old fashion when it comes to dating.  But I’ve also been told that as a woman all I have to do is smile at a man from across the room that I’m interested in meeting.  And if he is interested he will walk over and say hi.  Again good advice, but hasn’t worked for me :/

I’m sharing this advice in hopes it will be helpful for someone.  If it works for you let me know ;)

I’ve always been a positive person and believe in love.  I am a true hopeless romantic.  I love romantic movies and the big grand gesture that the man does for the woman he loves.  I know it’s a movie, but I do believe that can happen in real life.  After a failed marriage and 3 years of dating and I’m currently as single as it gets (literally zero prospects currently!), it would be easy for me to become cynical or bitter.  But I refuse!  I will always believe in love.  I still believe the right man is out there for me somewhere.  And we will find each other when the time is right.  


Dress: Good American (my most worn dress ever!!) | Necklace: Lana Jewelry, similar under $40

8 thoughts on “My Experience with Dating After Divorce

  1. Rachel,
    You have done the hard part. And you said it yourself, “ you know what you want”. And if I may add one thing, date without expectations. Meaning , have fun, and be you. You may make friends along the way. You absolutely deserve happiness.

  2. I did not even get through half of this before you opened my eyes. I also was in a 15 year relationship no kids or marriage but hurts all the same. I have been paralyzed in fear, thank you for giving me another way to look at it.

  3. As a almost-30 gal I can say I find SO hard to find the age gap where man are whiling to settle, they’re either living their best late 20s life or taking it to the next level on the first date. As a true hopeless romantic myself I believe things will find their way – but also can I give it a little push?

  4. Almost 41 here, was married for 16 yrs, single for 3 yrs. it’s hard as heck dating in this day and age!! I also have a child and live in a small city which makes it even harder to meet men. Dating sites are terrible! The longer I’m single the more I don’t even want to put in the effort to date.

  5. Great blog post! I’m 30 and single as well. I haven’t been married, and I haven’t had children. Everyone tells me I am in a great position because I am still young and don’t have children, but I’d argue and say otherwise! I feel like I’m in the category you mentioned in the post…. “Why haven’t you been married? What’s wrong with you? Hah!” Yes you might be lonely single, but you have a big family, children, and friends to keep you busy! That is such a beautiful thing to have in your corner. I had two long relationships in my 20s, and I am struggling feeling like my prime time has run out and those two men just wasted my time! I know that isn’t true, but I’m sure it’s a struggle for everyone past their 20s. Trying to move forward rather than dwelling in the past, I just moved to a new city in a different state. I thought exploring a new bigger town might help. I haven’t had much luck so far, but getting away from the old memories has been cleansing. I am more lonely now than I was before, but I am finding myself more being away from friends and family. I’m not saying dump your friends and family, but maybe a solo trip or two might lead to a possibility for you? Pick a bucket list type event you’ve always wanted to do and do it! And do it solo! I want to do that now more than ever before! I always wind up meeting people waiting in line for a hot dog at a ball game or chatting with a guy at the same hotel I’m staying at, etc. They say you’ll meet someone when you least expect it, and I feel like traveling alone or doing events alone is exactly where I would least expect to meet someone I would wind up with for the rest of my life. It also has that romantic fairy tale story feel as well! Just a thought?!

  6. OMG… I feel like I’m reading my diary!! I’m 49 (a young 49 😊) and been divorced from a 20yr marriage for 7 yrs now. Dated someone for 2-1/2yrs to realize we were going in separate directions and not I’m back in that dating pool again. Hate it! The person I dated recently was 4yrs younger than me and I was concerned about that at first. But not I’m thinking I need to date 4yrs older than myself? Who knows…. I just wish all the single ladies out there the best and stay safe!! Uugghhh

  7. Omg! I loved this! I seriously can not wait to hear more! I went and met someone last weekend… from a dating app… ugh! I thought what the heck am I thinking. This guy is something else. Nice but not for me. I almost deleted the app but my sister said to try and give it a little longer. Even my ex husband, which we are very good friends now said the same thing. Gotta get through all the weird ones to find the good one. Well last night, someone new popped up! I plan on meeting him over the weekend. So far he seems like a total gentleman, we have so much in common! Even more than I ever did with my ex husband. It was just one thing after another. Great conversation, no sexual talk, (which can be very off putting). A part of me thinks, maybe this is too good to be true… well we shall see what happens. Maybe it’ll be a complete bust. But like you, I’m a total romantic and I have to believe that someone, my person, is out there. I love how you put it, that none of the dates are a waste of time. So I appreciate you saying that. Thanks for this post and I look forward to more! 💗

  8. Rachel! I loved reading your story, As a divorced mom myself I resonate and relate!!! What a journey, my dating after divorce journey totally continuously has brought up all my stuff for healing. Did you get a dating coach for support after? I think that was the best choice I could’ve made. I’m a life coach now largely because of all I’ve learnt on the journey and now I’m with the most incredible man ever. I already had a real passion for helping women get results, but this def amplified it. I wish you all the best with your dating journey. Here’s to love. Don’t give up!

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