From Filofax to iPhone: One Mom's Journey Back into the World of Dating

My friend, Jodi Rosen, is our guest blogger today. She's funny, smart and charitable, but most importantly she's the mother of two beautiful children. Jodi also happens to be divorced and is navigating through the challenges of being a single parent. She's found it to be somewhat of a balancing act to be both mom and "back in the dating scene."  Enjoy Jodi's humorous take on the situation!


Just make sure the lights are off and you've had a few glasses of wine...

These were the words of advice from a happily married friend as I began to realize that dating again meant I would actually have to kiss (and yes, one day be intimate with) another man.


Dating again at 38 is definitely different. Eleven years later, I think back to when I met my ex-husband and he used his landline phone to call and ask me out.  Of course we had cell phones, but minutes were expensive and people used cell phones differently.  I remember one time when we first started dating, I called him from a pay phone while out on a girl's night to see if he was going out later and if we could meet up.

While in 1999 we did have email, we used it for work, not to court each other. Online dating barely existed outside of people meeting in chat rooms. I couldn't "Google him", check out his career profile on LinkedIn or follow him on Twitter. Texting did not exist.

Now when I meet a man, my girlfriends rush to their computers to look at his Facebook profile. After a date, he may text me, call my cell, send me an email or ask me to be his friend on Facebook. I've had to learn how to text and understand all the short hand associated with it. I upgraded my Blackberry to an iPhone to be sure my suitors can always reach me. I've had to learn what it means to block a "friend" on Facebook, should there be a bad break-up.

For a girl who used to have to call her sister for help downloading photos off her camera, this dating thing has really pushed my technology skills to the limit! (I know that secretly my sister, the technology savvy one in our family, is really proud of me.)

So yes, the technology advances over the last eleven years have changed the dating landscape. So has having two children.

Deciding to get divorced was the hardest decision I have ever made; primarily because of Riley and Blake. My daughter, Riley, is 5.5 years old and my son, Blake, is 2.5 years old. So much time and consideration went into my decision; ensuring that Riley and Blake would be fine, no, more than fine... fabulous was my main concern. Nearly a year later, they are fabulous and we have redefined what family looks like for the three of us.

With that piece of background on my most precious children, I am very much a single mom without a lot of help so figuring out how to keep them out of the dating mix is definitely a challenge. Luckily, my kids really don't know what a "boyfriend" is or what it means for mommy "to date". They love helping me "get fancy' when I go out and they are eager to know who I am going out with (most of the time I simply say my girlfriends). But finding a man who I would let into my world, to know Riley and Blake, is something I am very thoughtful about.

Yes, dating at 38 means I have met men who are divorced, often with 2, 3 or 4 children from their previous marriage. I have to consider how blending two families would impact my kids. I've dated men who have never been married or had children and wonder what my crazy, busy mommy lifestyle looks like to them. I remember being ready to go out on one of my first dates (in 11 years mind you) and after spending too long in the bathroom, came downstairs only to have Blake rub his M&M's smeared hands all over my outfit.

So while there are many important considerations regarding dating and my kids, on a more shallow note, they have forever impacted my dating life as being pregnant two times has permanently changed my body. While I think it is fair to say that most of us who have given birth to our beautiful children would consider it the biggest gift of our lives, let's be honest these lovely babies leave us with many gifts too. Stretch marks, saggy skin and "girls" who have suddenly decided to move south. I just wonder how another man will view these fabulous "gifts".

I guess I used to know rules about how many dates you are supposed to wait to kiss a man, but I have long since forgotten this now very useful piece of information. Other important nuggets of dating information I believe I threw away with my Filofax in 1999 include rules about calling to say thank you (or not calling if the date was a dud).

I've also learned that I needed a refresher course on how to manage dating multiple men at a time. It seems like it was so much easier when I was in my 20's and only had to juggle dating and work. Now, it is nearly impossible to be mommy-of-the-year, work, manage the house, keep up friendships, be a good sister/daughter/aunt/granddaughter, have a moment to myself and date more than one person. With the amount of brain cells I have lost after having two babies, not to mention simply being too scattered with my day-to-day life and functioning consistently on 5-hours of sleep, I have been victim of messing up names and facts. No thank you, I think mutual monogamy is all I can handle at this point in my life.

It is has been nearly a year since that friend gave me the advice about the need for darkness and wine and I am happy to say that there is one special guy who I prefer to kiss in the sunlight, wine optional.


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  • Loved the post Jodi. How do you manage to be a single mom in every sense of the word, a working mom and look so fabulous all the time? Ever since I had my daughter, I have gained a better appreciation for women who do this alone. I'm in awe. Thanks for sharing.

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