Awkward Brunch: in Which Adonis and I Bump Into Each Other on a Date

by Molly Undercover on August 22, 2017

Like all real things, there is a complicated side to ‘uncomplicated’.  

My dream date with Adonis , for example. It was lovely, but puzzling. In between dates, we have been practically strangers to each other. He’ll ignore my texts until he wants to talk to me. Much of our lives are kept sealed away like nuclear waste. I actually like that. But

There are times when I question whether I have the stomach. 

This past Saturday felt like too much. I went to a breakfast cafe with Tim for a fun mom-and-kid breakfast.

I made sure I was on my game, beauty-wise, as I usually try to do. I live in the same neighborhood with Adonis, and considered ahead of time that it could happen that we’d run into each other. I wore a cute bare-shouldered top, hair in beachy waves, and a glossy red lip. As Tim and I were finishing our trendy plates, in saunters Adonis with a beautiful lady conspicuously dressed in the previous night’s date-dress. 

It’s ok. We’ve dated, that’s all. But what was awkward was that he hid his face. I tried to catch his eye. I just wanted to maybe just to give him a wink, a knowing glance to let him know ‘I see you. Rock on with your sexy self’. It would have been a human and decent thing for him to do to give a hello. In my opinion, it is not nice to ignore people if they’re an object of your affections. 

As Tim and I left, I did what I probably shouldn’t have; I glanced backto see if I was being seen.  I almost turned into a pillar of salt; the lovely lady was gazing over her shoulder at me!Why was she watching me? The next thought I had sucked. Had he gone through all of the same activities of MY dream date he and I had shared, but with her, the night before? Was it all just a routine, not real, and an act? Was I just a passive subject in his self-absorbed Adonis Show?

I thought, jokingly in my mind, about how, later, I’d tease Adonis, saying that I didn’t say hi to him because I was just trying to be discreet, knowing Adonis would surely be jealous of my captivating date (Tim). 

Is this guy a snake or just a guy who is honest about women, and makes no promises? What do you think?



Happy Eclipse Day!

by Molly Undercover on August 21, 2017

I love the idea of experiencing a reversal of night and day. Illumination in the shadows. Feeling very trippy and emotional. It’s also the first day of seventh grade for Tim. God, I cannot believe how fast time has flown! He’s at the same school he started at when he was three, and it’s crazy to see how all the kids have changed in what feels like literally a FEW years to me. 

STRUGGLING to get work done today. Too much excitement in the air. 

Also, does it mean something if a man I’ve been casually dating lately with wants to watch the once-in-a-lifetime in our region solar eclipse with me? That feels very heavy and even relationship-y! I’m not sure I’m cool with the conclusions he might draw if I took him up on his invitation–might infringe on my single self. Or am I being a worry wart? 

{ 1 comment }

Dating Horrors, Molly Undercover Version

by Molly Undercover on August 21, 2017

It’s time for another round of dating horror stories:

A date with a guy that was not nearly as hot as I’d first thought:

I am getting over being sick and only out with this dude due to boredom. This guy is AWFUL to talk to. When a guy launches into a speech on the first date “I’m almost too nice. . . “: methinks thou dost protest too much? Why are you telling me this? You are either really boring, or you’re a monster! When he gets up to go to the bathroom I decide to risk asking him about his politics when he returns. It’s been a rough political season and this could be an easy way to find out whether he’s got ANY potential or not. If we can’t talk intelligently about what’s going on in the world, forget it. Well, he returns and I waste no time. Turns out we cannot talk intelligently. And he’s not cute. All I can think about is how people in earshot must be so annoyed to have to listen to our attempt to connect. It’s like nails on a blackboard. 

It gets better though. As I was leaving the nightmare awkward date, above, I looked to my right and realized The Centaur had been sitting there the whole time, hearing every word. This was before I’d called the Centaur but after I’d met him and got his number.

At least it gave me a funny excuse to text The Centaur a few days later, and a good conversation starter and bonding point to talk about what a disaster that date had been. Just another embarrassing Centaur experience.

Sorry, the role of ‘My Baby Boy’ is already taken:

Then there’s the night where I was hanging out with a guy that I’d pegged as quite confident, cool, and cute. We started to make out a little. . . whoo hoo!! Kissing is fun! But then, something so strange. Abruptly, his face turned away from me, his left hand sliding up to mouth. He’d stopped kissing me to suck his thumb. He gently embraced his cheek with his palm. What about me? I want a gentle embrace! I mean. . .I’m ok with it, I get it. It’s a tough world out there, and if there’s something that brings you comfort and hurts no one, by all means, you do You! But right now?  Your thumb is better than my luscious lips? Even worse – was he showing me he needs a mama? It doesn’t help that Mr. Confident here was substantially younger than me. Forget it! That slot, of baby boy, is filled in my life. I don’t need an overgrown child hanging around, thank you! 

DO NOT pet the feral rats:

Another very cute guy, I met while out for a walk in my city neighborhood. (In hindsight, red flag, obviously – be careful when somebody picks you up on the street!) We got a drink and got to talking. At first he told me he lived alone. I pressed. I got excited, it seems we had something in common! We were both going through divorces, with kids. But, as I pressed, I realized he was avoiding answering my questions about it his family life. Here’s why: actually after some questioning I learned he was not living alone. Actually, he was still living with his wife, the mother of his children, and she didn’t know he was out picking up ladies AND he’d just right then lied.

Very ratty. I should have known by the way he scurried along the gutter. Their divorce wasn’t even fully decided on!!! Why do men do stuff like this? I got the heck out of there. This dude had NO business talking to me until he sorted this stuff out with his wife. Infuriating and icky!

Wishing you better dates,

Molly Undercover

{ 1 comment }

Single Mama Bear and The Centaur

by Molly Undercover on August 20, 2017

He showed me his and I showed him mine. . . 

Nicknames, that is.  

‘Wild Animal Man’ aka, ‘The Centaur’ revealed that I’m not the only one giving pet names! Awwww. . . .

The Centaur doesn’t talk about feels. For example, he’s never, ever said “I like you a lot” or “I think you’re pretty.” This may seem like a bad thing—but bear with me! That quality certainly keeps my walls up, which is kinda just the way I want it right now. And he has other lovely qualities: he’s fetching, he’s passionate for life, and he’s great with his dog. He is very tall, with broad shoulders and sinewy limbs. Chocolate chip eyes, olive complexion, a mess of dark, long wild hair all over the place. Untamed, sexy.

I always get a little flustered when I see him and do weird stuff like spilling beer all over him, having awkward first dates with other men while sitting next to him the whole time, tripping over my feet like an idiot or accidentally sending him texts about himself meant for my besties. It almost seems like there is something about the Centaur that’s meant to get me SO flustered that I eventually give up, stop overthinking, and stop trying to control my reality.

Our casual arrangement was not the type of thing that progresses to a more serious relationship. But one day we chanced to be at a show together and I met a bunch of his friends. I didn’t think a lot of it. But later he came over to where I was hanging out. He was gazing at me with a goofy look on his usually distant face. His head was back, and he was half-grinning and looking at me as if he’d never seen me before in his life.

Later, I went up to the front of the crowd to enjoy the last band. He popped up beside me and we had fun like we’d never had before. Dancing together, goofing off with his friends and loving the music. As the band took a break he leaned into me. He’s so tall. He has to stoop to talk closely to me. Swoon. The rest of the scene faded out and I was visually, olfactorily and physically fixated on his undomesticated presence.

He said something to me along the lines of “My friend wanted to know who I was flirting with and I was like: ‘Oh, that’s just Mama Bear’ and she was like, ‘THAT’S Mama Bear? But, she’s really beautiful!’ and I was like. . . ‘DUH!’”

Did a grown man just use ‘DUH’ in an attempt to compliment me?

:::::Cool story, bro:::: But also, his friends have had a nickname for me? Meaning he talks about me when we’re apart? My head spun a little at the awkward compliment. 

I decided it was time and told him about how we call him the Centaur. 

Back to the music show. He paused a moment. And then, I could swear I saw his chest puff just a little, he rocked back on his heels, and nodded. “I like it,” he said with a grin as the band started to play and we began to dance again. 

About the Nicknames:

A little background on how my nicknames for him evolved: ‘The Centaur’ was coined by a mutual friend one night, after this undomesticated man-person had stomped around at a party in only cowboy boots and sparkly spandex. It was quite a sight. The nickname just fit his oversized presence. ‘Wild Animal Man’ came from another friend who exclaimed that he was a wild animal when I recounted to her how  he’d curled up one weeknight right on my front porch and fell asleep, snoring like an bear, feet sticking eighteen inches off the porch furniture.

I LOVE the nickname ‘Mama Bear’! I like it so much I almost want to trade out the name Molly Undercover for it! It’s cute, and also fierce. When The Centaur moves on, as I’m sure he will sooner or later, I’ve decided I get to keep this nickname. And I love it. Thanks, hairy and huge Wild Animal Man. 


Dream Date with Adonis

by Molly Undercover on August 19, 2017

A date so good that I’m not even sure it really happened. 

It’s the opposite of  dating horror stories. While I want to recount dates like this to each of my friends and family, they don’t want to hear it. But I want to tell about it, if you’re interested.

James Dean + a satyr + a Greek god = ‘Adonis’ 

This dream date story involves ‘Adonis’ (at least that’s what I’ll call him). Adonis is a motorcycle-riding, vintage-car restoring pilot. He’s an artist, poet and musician with a confident swagger, broad shoulders, and green-blue-brown eyes.

He’s not looking for anything committed or serious. When we are not together, we don’t talk or text much (I have my friends for that!) and there are no promises. Just the present moment, which is, for me and for now, perfect.

It was to be our second date. The afternoon of the planned date, he texted to say that he really felt like flying in his meticulously restored vintage plane, and would I like to join? Terrifying, but come on! Who says no to an offer like that? Plus, he’d been a legitimate pilot for twenty years. I trusted he’d keep us alive, and if we did crash and die, at least I’d be having an amazing time with a hot guy in the process. There are worse ways to go.

Getting ready for a good date is approximately 55% of the fun.

I called just before we were to meet, to ask if there were any clothing requirements for flying. He said no, and I decided on something timeless, and not too restrictive, that I hoped would match the old Cessna: dark, flared, high-waisted jeans, a bright colored sleeveless top with a cute peter pan collar, and strappy red sandals. He asked me to hold off for a few more minutes because he was busy preening. “Even if someone beautiful wasn’t about to come over I’d [want to look good]. . . ” he joked.

Maybe overly smooth, but Adonis has got game, I’ll give him that.

His apartment is an old victorian place full of patina. His artwork, books, musical instruments, and antique furniture filled the high-ceilinged rooms. We chatted about the possibility of our death by airplane crash over sparkling water. Driving to the small airport, we conversed about passionate living and friendship. He quoted Kerouac. It was truly an inspired exchange. I LOVE a good conversation. If that conversation had been the whole date, it would have been a dream in itself! But that wasn’t the end at all. . . . 

The airport was bathed in dusk. First, he performed what appeared to be a quite serious safety inspection of the very sexy airplane he’d restored to mint condition over a decade with his dad and best friends. As he nerded out over the aged Cessna, I could sense his relationship with it. I was touched that he’d share this part of his life with me. He took some time to give me a tour and explain the science behind how tough it would be to crash the thing.  

We rolled her out to the open field beside the runway. He snapped about a hundred pictures of me on my phone with the airplane against an orange-pink sky. I basked in the attention. I now have the souvenirs of this experience, great photos that he later that evening, spent some time cropping and filtering to just how he liked them. His favorite, he edited “for your grandchildren” he said. (I’d show the pics to you, but then I’d have to kill you :-))

We took off and he showed off his skills for a while. Then I flew the plane! As I observed him in his element, I felt enchanted. He decided he wanted to try landing on grass, and warned that it could feel bumpy but would be fine. As it turned out, the landing was one of the most graceful things I’ve experienced. I hopped out, full of adrenaline and blissed out and started dancing. 


It continued to unfold. . . 

Back at his apartment, there was just enough red wine and good lighting. We sang folk songs. He played guitar; he sang songs I didn’t know, too, with gusto. At a few points, he’d thrust a harmonica or a violin at me to solo (both of which I happened to used to love to play a million years ago but suck at now.) We danced together and he lifted me in the air, spinning me around. We went outside and played in the pouring rain like toddlers. We ordered food in. We had incredible conversations about philosophy, work, jealousy, and more. He serenaded me in candlelight, a song he’d written on his guitar. 

By the time the date ended, I was pretty convinced that I am a captivating princess witch who can fly, and who should expect nothing less than this level of sensuality and romance. I am basically ruined for average dates now.

Up your game, dudes!!

I love the way, during this single phase in my life, I am collecting so many experiences and memories as I date different men. 

If you got this far without barfing, thank you. And tell me your dream date story!


Molly Undercover


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?


Early Summer Update and the Ex’s New Girl

by Molly Undercover on June 26, 2017

June has been a single parenting/elder care/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: Adonis, a very romantic and fetching pilot; Centaur/Wild Animal Man; and, Cat Guy, (I know, last you heard, I broke it off. Well, it’s complicated). 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 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 and are stubborn about accepting help. Their situation is critical. 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.


{ 1 comment }

Texting while Dating: A Cautionary Tale

by Molly Undercover on May 24, 2017

Some typos can’t be deleted.

Introducing Wild Animal Man/The Centaur. 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! Also I’m pretty lucky that I can run stuff like this by Miss Single Mama)

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


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. I was just looking for fun and flirtation. He reassured me that fun was the whole idea. Putting me at ease, he stated that he’d probably be a awkward when we met because he thought I was gorgeous! I got excited. 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 at a fun neighborhood bar. I was still nervous that he might expect something. I just wanted to flirt. I was excited 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. Then I changed my mind, and we kissed. OMG. I was kissing a man! I had almost forgotten how fun it felt to kiss. And I had thought this would never happen again.

We enjoyed each other’s company for a little while, then I had to go and pick up my son. 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 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. We are cooperative but tense. I’m trying to be cool and functional and reasonable, but inside I’m still dealing with some strong feelings , 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 Tim 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. 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?