Redefining Family Vacations

by Molly Undercover on June 28, 2017

I’m going to need to be complainey here just for a minute, ok?  I promise, I’ll get it out of my system so we can get back to interesting and fun things tomorrow. But today, I had that ‘cry in the car’ kind of day, and each of my friends and siblings have done their patient duty of listening to me prattle this already month, and now it’s your turn, dear readers.

Lately I feel like I’ve slid back months in the process of letting go of my marriage.

Today, it’s the process of planning vacations that sets me off (I know, I’m pretty lucky if this is the type of thing that gets me upset).

I’m planning summer trips and adventures. Tim has his two middle-school aged cousins in town this week, and life is good. They are so cute together, cracking each other up all day, developing inside jokes and having fun. It’s early summer and we have tons of plans with family for the Fourth of July. I also have weeks of vacation saved up at work, and only need to make a plan in order to be on the road somewhere. I’m in a great situation.

But for some reason, I am having a terrible time committing to any particular plan for weekend trips or longer vacations. Even for this weekend with the cousins here. On the surface, it’s just indecision, but if I sit with my feelings a little bit I realize I’m feeling alone. This is the kind of stuff I used to get heavy input from Tim’s dad on. My decision-making skills are weakened from years of letting my spouse take the lead. I’m not proud of it, but it’s true.

In addition, I worry that every plan I come up with will be inadequate. To me, vacation = family time. And up until recently, family was always the three of us; Tim, his dad, and me. At a time like this, I would have enjoyed sharing the fun of seeing the cousins together with Tim’s Dad. On vacation with just Tim and I, I’m afraid I’m not enough; not interesting enough, not good enough at planning. And I can never make our family go back to what it used to be for Tim, and what if a vacation with me as the only adult is just no fun?

None of these negative feelings change the situation that brought me here though. Vacations with Tim’s dad didn’t make up for a marriage that didn’t work. Yes, vacations were happy experiences, but I tried to use to make up for weeks and months of isolation and lack of support in my relationship.

It’s a good thing that I’m no longer sitting passively by and letting some man make decisions for me all the time, and feeling unhappy. It’s a good thing that I have a choice over how I spend my time, and that I am lucky enough to have vacation time and good friends and family to plan things with. It’s not light. It’s not fun, but it is what it is.

Today at work I went out for a walk. We have a little nature trail you can take that leads to a coffee shop. I walked with stress about whether I could give Tim enough fun this summer running through my mind. Then, I just started to feel like it was all pointless. What’s the point of having fun if families can break up, people get old and die, and everything can go to hell? Some dark shit was running through my mind.

Then I noticed. Some kind of fluffy wildflowers along the path were sending seed puffs waving in the wind and flying up into the sun. The weather was just about exactly 80 degrees, with light streaks of clouds and no humidity. The breeze blew across my face. I got lost in the moment. The words came to my mind, “All we have is Presence,” meaning, the only thing that matters is right now. Suddenly the pressure to create the perfect experiences when Tim and I are together lightened, and I realized that the elegance of every little moment matters so much more.

Especially with how quick he is growing up! My experience on this walk made me want to just hang out with Tim, just let go of any idea that I need to be ultra-fun. I like this super-zen, wise version of me. Maybe this is how I single mom, at my best? Still, I gotta plan a vacation. There’s so many places I want to go, both as a free single lady and with Tim. I’d love to take him on a bunch of weekend trips and a road trip out west. I would love to read comments – have you had any good single mama adventures with your kids?

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Early Summer Update and the Ex’s New Girl

by Molly Undercover on June 26, 2017

June has been a single parenting/adult child of dementia patient/dating/work/social whirlwind! The highlights since I’ve last posted are the following:

  • Tim stayed with his Dad for a week and I used the eerily free time to catch up on my social life–that’s why there have been so few posts!  I went to my first music festival, had one of my first parties at my house as a single to host some awesome new work friends, and took a quick flight for a weekend getaway with a girlfriend.
  • I took Tim camping. First time just the two of us. Tim set up the tent! I was very proud.
  • Tim met his Dad’s new girlfriend.
  • The dissolution of our marriage is not yet final but the lawyer’s working on it. This requires equal doses of paperwork and dealing with my sad and angry feelings. We technically hit our seventeen year anniversary this month, ironically on the day before the ex introduced Tim to the new woman in his life.  And no, I don’t approve that my ex chose to do that while we are still legally married, but I’m picking my battles.
  • I went on a few amazing dates myself! Nothing serious, though. In the mix: a very romantic, artistic, and gorgeous pilot; Centaur/Wild Animal Man; and from time to time, Cat Guy, who was looking for a relationship, but he now knows I date some other fellows, and that I’m keeping it light. I got a few asks for dates from people I just didn’t have time to see. The dating life is exhausting and fun.
  • My sister moved out of her family home and into an apartment by herself, starting her own, difficult single mama journey many hours away. My heart’s breaking for her and I’m concerned for the hurdles she has ahead.
  • My parents, two hours away, have reached a crisis point due to the onset of dementia – Alzheimers, (likely, dad), and Speech Aphasia, (confirmed and rapidly progessing, mom). They still live on their own, for now, and are pretty stubborn about accepting help. Their situation is terrifying and needs urgent attention. My newly single sister is taking a leave of absence to care for them while she can.

I feel like the true sandwich generation! Single mom, parents need care, and I’m still trying to achieve in my career, make a contribution to this world, and parent my pre-teen single. It feels busy, to say the least.

Of all of these joys and stressors, meeting the ex’s new girlfriend, having Tim meet her, definitely threw me for the biggest loop this month.

I’ve been determined since March 6 of this year to graduate from my grief over the end of my marriage. I don’t want to mope forever! I felt like I lost months of progress the week Tim met his dad’s new woman. I’ve got all kinds of feelings about it. Beforehand, I was just concerned that she might not be cool, or might not be good to my 12-year-old Tim. But she seems like a normal person and Tim really liked her. That brings me to my next worry. What if he likes her too much, and she’s gone in six months or a year? That seems like so much for a kid to deal with. And then, there are the bizarre feelings of jealousy. What do I care if my ex is with someone new? I know completely that he’s not right for me, yet it feels upsetting to think of him being with her. I catch myself in the middle of thoughts I’m not proud of, that their relationship fails spectacularly and that they both end up suffering. Not feelings I want to feel. I guess these tell me that I have more progress I need to make in letting go of the past and of my anger and bitterness.


Birds and Bees

by Molly Undercover on May 27, 2017

A great resource for any of you considering a divorce
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!




Texting while Dating: A Cautionary Tale

by Molly Undercover on May 24, 2017

Some typos can’t be deleted.

Introducing Wild Animal Man. I’ll explain plenty more about him in future posts. All you need to know for the purpose of this tale is, we first met when we randomly ran into each other twice in two weeks, and then we had one great date. Also, his name might seem like an insult, but I mean it in the very best of ways! He’s wild and lovely. More on that later.

On one fateful Friday, I knew I wanted to see Wild Animal Man again, so I texted to ask him for just that.

Me: how’s it going?
Wild Man: Pretty good, Molly.
Me: I’d like to see you again. Can we make that happen?
Wild Man: Soon! I’ve just been so busy working this week. . . I need to get some free time soon so we can hang out!

There were some emojis, an illustrated laundry list of his work, and some flirty words included. So far so good, right? But unfortunately, this was one of those annoying texting situations where it was hard to tell what the real meaning was. Had he really been working hard, or was that just an excuse? Was this an awesome message? Or a terrible one?

As one does in these situations, I enlisted a trusted friend.

(Oh the joy of having wise women around you to interpret the cryptic man-text!)

MSM: Hey! What’s going on with Wild Man?
Me: I’m texting with him right now! I don’t even know if he likes me.
MSM: Send the text! I’ll analyze.

I rapidly took a screen grab of my exchange with him, and promptly sent the picture to. . .

You guessed it. . .

Wild Animal Man.

“No. no no no No NO!!!! HOW do I undo this???” I thought in a panic as the ‘sending’ bar traveled relentlessly across the screen. In a ridiculous attempt at damage control, I texted him again, playing dumb:

Me: Oh! that’s how a screenshot works on the iPhone!


Wild Man: Thanks for the admiration 😉

So. Embarrassing. Since the above incident, I’ve attempted to retain some tiny shred of my dignity by not mentioning this to Wild Animal Man ever, EVER again. I’m guessing from his response at the end there that he figured out exactly what happened, and my little attempt at cleanup only made it worse, a la Bridget Jones. Gah!

My critical errors: 1) not picking up the phone and just calling him. Remember phone calls? 2)These two conversations, the one with Ms. Single Mama and the one with Wild Animal Man, were basically simultaneous. 3)Moving too fast.

Want to minimize damage potential when texting with a date? Here’s some advice:

  • Keep texts brief, for in-the-moment facts, not feelings.
  • Call him on the phone. Or, even better, hang out in person!
  • Avoid texting more than one person at a time and avoid texting too fast. It only takes one slip of a finger to make a big mess!
  • Consider NOT broadcasting his messages to others in the first place! And, men, fair warning: We do share from time to time.
  • Your children may know how to get into your phone. If that’s likely in your case, keep it Disney!

On the positive side, my little gaff may have accidentally shown a little of the truth, which is that I think this guy’s the bee’s knees! And, it didn’t seem to bother him too much, because he has turned up a few times since then. Hey, somebody’s gotta get egg on their face and show they like the other person at some point, right? Might as well be now.

It’s never been easier to find and communicate with the objects of our admiration–and to make dumb mistakes at a rapid pace, too! Do you have a super embarrassing digital-age blooper under your dating belt? Make me feel better! Leave it in the comments.

With Love,

Molly Undercover


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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