Very First Date After a Divorce

by Molly Undercover on May 17, 2017

To date post divorce you just have to dive in.

In her famous Ted talk on vulnerability, Brené Brown says, “vulnerability is. . . the first date after a divorce” I couldn’t agree more. I was terrified before my first date! Three months after my husband and I separated, I wasn’t looking for someone to date yet. I felt repulsed by the idea of being in a relationship again and hopeless that I’d never be able to connect with a man again. But I was also worried that if I passed up dates, I’d calcify and never get back in the game. I did miss romance, for sure. When someone cute but not ‘my type’ asked me out, my fear of becoming a lonely cat lady if I didn’t start dating pushed me to just try it and see what happened.

And then the first post-divorce date finally happened…

Over text messages, I awkwardly informed him that he was a true rebound, meaning: I was just looking for fun and flirtation. He reassured me that we were just going to have fun together, no matter what. Putting me at ease, he stated that he’d probably be a nervous dork and super awkward at first when we met because he thought I was gorgeous! This brought on a little ease and excitement. I arranged for my son to go home with a friend so that I could meet him for a patio happy hour one afternoon.

We met on a lovely spring day at a fun neighborhood bar. I was still nervous that he might expect something I didn’t have to give at the time, like a relationship, or even sex. I just wanted to flirt. I was excited too–to show up and trying something new.

We were the only people there, which amped up the awkward feeling. But contrary to his warning, my date was actually laid back and fun, totally confident, and looked and smelled great. He put me at complete ease.

As we played giant Jenga on the patio, his confidence and masculine presence infused me with my own confidence. He was starting to get a little handsy. Brushing my wrists and finding other ways to make contact as we goofed around and talked. He was making me laugh and dammit, this was fun! At one point he leaned in for a kiss. Nervous and feeling vulnerable, I did the old ‘cheek turn’ trick and let him plant one there. It felt great, so I changed my mind, and we kissed for a little bit. I was kissing a man! I had almost forgotten how fun it felt to kiss.

We enjoyed each other’s company for a little while, then I had to go and pick up [Thegn]. I went from feeling closed off and hopeless that I’d ever date again to goofing around with a sexy man on a patio on a sunny June afternoon. If you’re like I was and a little scared to try out dating, know that it can be fun!

Based on what worked well for me about this, here’s my advice for the first date after becoming a single mom:

  • Be clear with him upfront if you’re on the rebound!
  • Obviously but worth stating: have your own way there and home and let someone know where you’ll be.
  • If you’ve been in a relationship for a while: don’t turn someone down because they are not ‘your type’. Someone very different might be just the thing!
  • Plan to keep it short. Happy hour or coffee when you’ll have to pick up your child is one idea. Your time is so precious as a single mom and realistically, you may not see this person again.
  • Just be yourself.
  • Be easy on yourself. You don’t have to meet prince charming on your first time out after marriage and parenting.
  • Remind yourself to be open and not compare your date to your old relationship. They are two totally different situations for many, many reasons.


Ms. Single Mama II , aka Molly Superspy

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The Kid’s First Birthday as a Single Mama

by Molly Undercover on May 16, 2017

I’m navigating Tim’s birthday as a single parent for the first time. I just had such a hot mess of a phone call with his Dad about it. Background: we’re cooperative, but keep the communication to a bare minimum. I’m trying to be cool and functional and reasonable, but inside I’m still dealing with some strong feelings about him, and I know it shows in my voice and my decisions.

Here’s what happened: I emailed an invite to a bunch of parents about a fun party night for Tim for his 12th birthday. I’m always so last minute about these things! Right after I pressed send, I panicked; should I have consulted with my ex before unilaterally planning? Would he be angry and retaliate? Would  be hurt if his dad wasn’t there for his party like he always has been in the past? On the other hand, I’ve always handled this kind of planning, and I don’t want to interact with the ex any more than I have to. Ugh! Minefield! Without resolving my decisions for myself, I hastily decided to just call his dad and fill him in.

My voice on the phone was fake polite, anxious, and over-compensating, with an edge of passive aggressive anger. In short, loaded down with baggage. I filled in the ex about the plan I’d made, and asked what he’d been hoping to do with Tim for a birthday celebration. He asked if he could take Tim for a birthday dinner on his actual birthday. Thinking that Tim might be sad if both parents weren’t there, I countered that maybe we should do it all together and invite some other relatives. Immediately I felt myself recoil from my own suggestion. I didn’t feel up to hanging out with my ex and his whole family! I stammered something about not being sure that was the best plan and ‘let’s work it out later’ and got off the phone. What a mess! Clearly I’m in no state to have a fun birthday dinner as a reconfigured family. (Happy birthday, son! Let me turn into an emotional mess all over your birthday dinner, isn’t this fun?) What was I thinking??

Here’s what I wasn’t being honest about: I’m assuming Tim’s going to be heartbroken to have only one parent there at a time. I’m trying to keep him from experiencing any more loss and pain than he already has. But if that hurts me, maybe it’s worse for him in the end? I think these are the questions we consider over and over in the process of becoming single parents, from the decision to separate or not to the way we navigate custody and holidays.

How do you keep birthdays and holidays fun and joyful, and how to deal gracefully with your child’s other parent?


Sad Clown in an Arcade

by Molly Undercover on May 15, 2017

Sitting in an arcade for Tim’s birthday party with a bunch of twelve year olds. This is pretty much the last place I want to be right now, since I just had a little bit of a break up conversation with Cat Guy, and now I need to be fun and cheerful. It can hardly be called a break up, because he’s only been around for three weeks. But he had already expressed so much interest in being around longer. I had started to fall for him a little.

“I need to recalibrate,” I told him as he looked at me with his deep eyes. “I’m struggling. I’m working on divorce paperwork and feeling heartbreak, and I don’t think the state I’m in is any kind of foundation for a relationship.”

Cat Guy took this news well, like a real grown man. Just kept looking into my eyes with his deep brown ones. Then he put his head on my shoulder and cursed softly.

Ugh! Why does this have to feel so hard? Cat guy wasn’t my boyfriend yet, but he is the first person to come even close to being a boyfriend, and he would be a ‘good’ one, at least on paper. He plans ahead to hang out, but he’s open to spontaneous fun, too. He has no idea what it’s like to be a parent, but he has shown nothing but enthusiasm to meet Tim. I get the feeling that he would do all that he can to integrate into our lives and seems attracted to me and Tim as a package. These are all things that are important to me if I ever get into a relationship again. Not only that, but he’s attractive. It SUCKS to be passing up on a relationship with this guy. But my gut says I’m just not ready, and that I need to protect my singleness fiercely. Listening to my gut again is one of my single mama superpowers, and I can’t abandon it no matter how much I want a boyfriend.

So, here I am, handling a sleepover party alone. I forgot orange juice and bacon for the morning. If I had a man around, we could divide forces; he could play with the kids while I run to the store. It’s little things like this, not to mention the desire for love and companionship, that make me want a man around, at least sometimes.

Runs to the store and companionship aren’t enough to lure me into a relationship right this moment. Like Calvin of Calvin and Hobbes, “happiness isn’t good enough for me. I demand euphoria!” And, I’ve got friends and neighbors who will pick stuff up from the store for me. I will soldier on, single, and keep going in this growth process a little longer, without cat guy.


Molly Undercover


Ms. Single Mama 2.0

by Molly Undercover on May 15, 2017

Hi! I’m Ms. Single Mama, version 2. A couple of years ago, I came across Ms. Single Mama and her blog. It was exactly one day after my (then) husband first told me he wanted to move out of our house. On the day I found Ms. Single Mama, I was sad, excited, and most of all, TOTALLY out of touch with the reality of the situation. For example, I had no idea 1) how hard it was going to be to go through the ending our 14-year marriage, and 2) how much better off, stronger, and happier I’d be once I became single. As I got to know Ms. Single Mama and got deeper into singledom myself, I’ve had plenty of time to study her ways and gone through some hilarious/awful/awesome single mama experiences that I’m dying to share with you and hear from you about.

A few more details about me: I got married young after minimal dating experience. In my youthful wisdom, I figured, what the hell? We love each other, what can go wrong? Ha, ha. It took us a year from that first time my ex revealed he wanted to leave to truly and mutually recognize our relationship was done. We have a twelve-year-old son Tim (I’ve changed his name, and I’ll be changing other names throughout my posts, for privacy). I’ve been separated from my ex for over a year. I’ve have only recently filed the divorce papers. I’m a badass, and this is hard, and I’m a hot mess sometimes! I’m not an expert; I just happen to be willing to reveal the whole experience to you hear, and eager to read your thoughts.

Moving forward, this blog is going to touch on many of the same topics it always has, but in my own voice. I’m in the middle of grieving, legally ending the marriage, getting to know myself, learning to parent single and to co-parent with Tim’s dad, and, of course, starting to date! And I want to talk with you about all of it.


Molly Undercover


Single Moms with (a few) Answers

by mssinglemama on February 17, 2016

My single mom friend and blogger, Emma Johnson, is such an inspiration.

I met her years ago at the 2012 BlogHer conference. At the time, she was just about to begin her own blog on being a single mother. Flash forward to today and she has tens of thousands of readers and is still a thriving, happy and successful single mother.

And recently she interviewed me for her awesome podcast, Like a Mother.

Listen here.

We spend about an hour talking about some of the hottest single mom topics: dating with children, moving past your ex-husband, finding happiness through acceptance.

I hope you enjoy!



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Hello, my lovelies.

by mssinglemama on August 30, 2014

It’s been a while. How are you, my beautiful readers?

So many of you are still here, finding this blog at the start of your journey as a single mom as you type in a search term looking for answers and support. Know that I miss you always, think of you constantly and wish I could be here, writing more. But life has to be lived right now.

Believe it or not, I miss my days as a single mother. Or maybe, I just miss my twenties. Either way… I miss you back.  But that was then and this is now. My “now” now involves our new baby, my not so little Benjamin, my two step children, the love of my life and my business. Phew. There’s a lot. BUT, I took a few hours tonight to finally, publish Ms. Single Mama Uncensored again.

I took the original eBook down years ago because it was such a hassle to manage and for you all to download and read. I still receive emails from readers weekly asking for a copy – so, here it is… Ms. Single Mama Uncensored for the Kindle on Amazon. If you don’t have a Kindle there is a Kindle app for the iPhone and probably for the Android, although don’t hold me to that.

Also, I haven’t read this in ages.

I need to re-write the ending and a bunch of other things, so stay tuned for an updated version.  ;  )

Download Ms. Single Mama Uncensored here. 

If you missed the details here they are:

The blog is just the beginning.

In Ms. Single Mama Uncensored the secrets are out. In the book you’ll find out…

  • How my ex-husband and I met and fell in love
  • More about the illusive Biker, my first single mom romance
  • Read the story about my first single mom crush
  • What really happened with Mr. Man
  • Why my fling with Cabin Man was so short lived
  • Details on how to have a happy and healthy sex life as a single mom along with tips on dating including touchy issues like when to tell him about your single mom status and when to introduce him to the kids.


What people are saying about Ms. Single Mama Uncensored (the eBook):

“There’s no difference to me between this book and something on a shelf at Barnes & Noble. I bought it and have been devouring in big gulps for the past few nights. Thank you!” – Jen C. of Follow Your Bliss ”

“OMG…I can NOT stop reading your book. You’re an INCREDIBLE writer. I’ve loved your blog all along – but your book is truly, truly incredible. I am healing so much in so many ways just by reading your experiences and knowing, once and for all, that I too will be ok. Thanks for putting your heart on your sleeve for the rest of us single moms!!!” – Ericka Sevilla, on Facebook.

“For anyone who is on the fence on whether or not to buy this book…DO IT! I am also a single mother and since i am only 21 i do not have any single mama friends to discuss the different experiences and emotions that we go through with, but reading this book has helped me in SO many ways! Everything that Alaina talks about while telling her story is something that any single mother can relate to. For me at least, it seemed like this book was custom made for me. I believe that after you read her whole uncensored story that those of you who haven’t really started to heal can finally begin the process, and those of you who aren’t single mama’s can truly appreciate what a single mama has to go through to be also be a GREAT mama! Thank you so much Alaina for sharing this story with us! I obviously LOVED it!” – Chelsea

A true page-turner this book pulls no punches. Ms. Sheer recounts stories from her personal life with humbling candor, drawing readers in with all the confidence of a best friend. Central to the theme of this book is Ms. Sheer’s emphatic advice to each and every single mom searching for Mr. Right. That advice? Love yourself. We’ve all heard it, plenty of us have brushed it off, but none of us have had it phrased quite so convincingly as Alaina Sheer has done in this book.” – Jennifer Parker, Boise Examiner

“On the outside, you seem so put together: smart, beautiful, successful, confident, and (now) in love. You are, indeed, all of those things, but the e-book also shows a very the human side of you: an everyday, normal woman, with the same obstacles, mistakes made, lessons learned, worries, and disappointments. Despite what you have gone through, you remained strong for yourself and Benjamin–and in telling your story, you also give other single moms, dads, and everyone else HOPE. That is truly inspiring.” – Jen C.

“Old posts are mixed with new stories and her insights and revelations fill the gaps, creating a smooth, easy to follow glimpse into her world. Sheer invites you into her world, and while I am not single nor a mother, the underlying themes of trusting and believing in yourself rang true to my heart. Ms Single Mama finds a way to balance romantic optimism with the realities of daily life, all the while ensuring the needs of her son Benjamin are met. As both Benjamin and her confidence grow, she slowly heals from her previously chaotic life.” – Amanda, Stack of Spines




Ms. Single Mama


Find Seth and I on our new blog, or follow me on Instagram @alaina_gray



The big announcement…

by mssinglemama on May 17, 2013

We have some rather big news, coming in a teeny, tiny package. More details on Beauty and the Biker. 



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Love from a reader and another single mom.

by mssinglemama on March 15, 2013

I love hearing from you, my readers. I receive so many, it is hard to respond to all of them. Know that I do try.

This email from Madison had to be shared. The fact that my blog helps all of you feel more confident, empowered, and inspired fills me with so much hope and happiness. You are all beautiful. You will all be loved again (by your true match). And, you are NOT alone.

Here’s Madison’s email… And she even attached a picture. 

Dear Alaina,

I stumbled onto your blog late one night while I was researching single mom dating statistics. lol. Classic right? A lonely single mom looking for validation from the web. I found validating and warm reassurance while reading your posts. Your positive attitude and honesty about your journey is inspiring. Sometimes I feel like I will never make it through this deep and dark era as I face motherhood alone. Then sometimes I hear/read stories like yours that give me a little push that I so badly need in the positive direction.

My name is Madison. I am 24 years old and single mom to two beautiful twin girls.. I never planned on being a single mom of course, but I was young when I got married and put up with an abusive husband for one year. I found myself with newborn twin daughters to raise at 20 and I somehow have made it this far. I am happy, brave, hopeful for our future but sometimes I need assurance that I am doing ok. I waitress and work as a secretary at a hospital and when my girls start Kindergarten this year, I can go back to school as I wont be paying a fortune on daycare anymore.

Between sleepless nights with sick little ones, and crying in my closet while I eat my secret stash of peanut butter M&M’s, I have become a real strong lady. I have survived these last 4 years by a customers generous 15.00 tip and by moms like you that stay positive. Thank you so very much mssinglemama, for giving me hope and for sharing your happiness with the web!



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How do you let go? On shared custody.

by mssinglemama on February 20, 2013

One of the most challenging aspects of single motherhood, or single parenthood, is adjusting to shared custody.

In many cases, as mine was until recently, you are legally obligated to send your child into your ex-spouse’s home regardless of whether or not your gut instinct is screaming at you that something is just “not right” about a step-sibling in the house or a step-parent or even their biological parent. You, in most cases, have to pack your child’s bag, put him into his or her little car seat and drive them directly into the Lion’s Den. Your child comes home, an emotional wreck. In Benjamin’s case, filthy, hungry and exhausted to boot.

Now, I am a bit jaded–from my own personal ex-experience being so downright awful–but there are obviously many situations that aren’t nearly as bad.  There are dreamy ex-spouses who actually communicate with you for the children’s sake, drop them off on time and pick them up on time. Feed them, clothe them, support them and continue to be a supportive co-parent by always putting the children first. I have yet to meet one of these, but I hear they exist.

So, what do you do when you have no options legally? In my case, it took something actually happening to Benjamin for us to be able to receive full custody with zero unsupervised visits at his father’s home. I can’t get into details, but it has been a harrowing ordeal, to say the least. All of those years my gut instinct was right. I regret ever sending him there. I regret not acting like a mad woman and hiring a fierce attorney to keep him from ever spending the night there. But, I can’t go back in time, only forward… and am relieved that it is over in a sense. No more sharing for this mama.

What advice do you have for each other on surviving the ex hand over? Any coping mechanisms you have learned that you can share with new single moms? Or do you just want to vent.

Do so in the comments. Can’t wait to read your thoughts on this.


A New Relationship: How to Tell the Kids

by mssinglemama on January 13, 2013

My single mama friend called me last night.

“Hey lady, I really need your advice on something,” she sounded fearful and scared. I thought the worst. Maybe she and her new man were breaking up.

“Charles and I are definitely going to get engaged,” they just know – as Seth and I did- that they are meant to be. And it’s lovely.

“That’s so exciting! I’m so happy for you. So, what’s the problem?”

“He will be moving in with us in December. So, it’s a long ways away, but I’m scared about how to tell Sarah. It’s always just been the two of us. What will it be like? Will she be upset? How did you tell Benjamin?”

She sounded so worried and concerned. Just this fact alone, told me her heart and head were in the right place. If a mother cares that much about her child’s transition into a new relationship, all will definitely be fine. I have met too many mothers over the years who put their relationships over their children. Welcoming, with open arms, ex-boyfriends who abused them or men who cheated on them back into their lives and their child’s lives. It’s upsetting, to say the least.

My friend’s daughter, Sarah, is in Kindergarten. A sweet, quiet, little girl who has never seen her mother with any boyfriend, not even her father. Here was my advice to her:

Read the rest here, on Beauty and the Biker.