When Did Drinking Stop Being Fun? / EP 146
Nov 04, 2026
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From Halloween wine to morning-after regret, a gentler way to change your relationship with alcohol this season
The Halloween I Twisted My Ankle
When my son was little, Halloween meant costumes, candy, and excited kids racing down the sidewalk. It also meant wine. While the superheroes and princesses collected candy, the parents had a tradition of their own, and one year I drank enough that I twisted my ankle.
I can laugh about it now. But underneath the funny story is a truer one: alcohol had become so woven into every celebration that I never stopped to ask whether it was actually making things better. How many of our drinking habits are really traditions we've never questioned?
When the Fun Quietly Fades
For most women, there's no dramatic moment when drinking stops being fun. It's quieter. One glass doesn't satisfy anymore. You look forward to the evening drink all afternoon, and then it underwhelms. You stand at a party with a glass in your hand, wondering, "Why am I doing this?"
Admitting that something you once enjoyed no longer feels good can be scary, especially when alcohol is tied to your friendships, career, and identity. After twenty years in the wine industry, I know that feeling. But you can outgrow something, even something that once felt like part of who you are.
The Morning-After Cycle
You know the morning. The sinking feeling before you even get out of bed. How much did I drink? Why didn't I stop at two? Why do I keep doing this? Then the promise: tonight will be different.
And then the day happens. Work, stress, everyone needing something. Around five o'clock, a glass of wine sounds nice. I had a hard day. I'll just have one. And the cycle starts again.
Over time, this stops being only about alcohol. It chips away at your self-trust, especially if you're the capable one everyone depends on. But repeating a behavior doesn't mean you can't change it. It means there's a pattern worth understanding.
What Alcohol Promises vs. What It Delivers
Alcohol promises relaxation, yet it disrupts sleep. It promises relief from anxiety, yet leaves you worrying about last night. It promises confidence while eroding self-trust. The most useful question I know is simple: "What am I asking alcohol to do for me?" If the answer is relaxation, connection, or permission to stop caring for everyone else for five minutes, that's valuable information. Now you can meet the real need.
Curious, Not Critical
Many of us believe that if we're hard enough on ourselves, we'll finally change. But shame keeps us stuck. Imagine a dear friend calling after a rough holiday party. You wouldn't call her hopeless. You'd ask what happened and what might help next time. Offer yourself that same kindness.
Your Holiday Freedom Experiment
Try this at your next gathering:
- Pause. Before reaching for a drink, notice where you are and what you're feeling.
- Get curious. Ask what you're hoping alcohol will do for you right now.
- Choose. Ask what would actually help you feel the way you want to feel: a festive alcohol-free drink, fresh air, a real conversation, or heading home early.
Every pause creates a little space between the urge and the action, and in that space, you get to choose.
What Do You Want to Remember?
When you look back on this holiday season, what do you want to remember: the drinks, or the moments? Rock bottom is optional. You can start answering that question today.
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