I had to drive into Seattle today. It's twenty minutes from my home, so a regular-enough trip, but until I found myself merging onto the 520 did I realize that I haven't driven in downtown Seattle in nearly 20 months. 
I've been there during the pandemic, a handful of times, but someone else was always driving. I haven't driven myself in downtown Seattle since before the entire globe was struck with an illness that closed down society. 
It was surreal, and tricky. The lanes are skinny, and there is no parking. The buildings tower over you and cut off your GPS signal. Traffic is just as bad as it ever was, the whole world seems to have returned to normal already. I guess I was the last holdout.
It is this, this returning to society after a long absence, that is represented in the reversed five of cups. 
I don't plan on going back to Seattle anytime soon. Driving in that hellhole for one morning was enough for another 20 months. Now that I'm back home, I'm going to channel the reversed five, clean the desk right in front of me, and watch some Thor. I'll imagine him clearing the traffic with one throw of Mjolnir - that'll help me get over the agony of Seattle driving.

​The Five of Cups upright is regret or grief about something that happened in the past, and it’s an indication that we should try to look forward and find the positives.

The Reversed five is this looking forward. It is moving on from defeat, letting go of sorrow and regrets, and doing our best to rejoin society after a setback.
 
Questions answered by the reversed Five of Cups:
Who? Someone moving forward 
What? Letting go
Where? Ahead of you
When? The last week of October; 5 days or weeks from now; When you let go
Why? “You can spend minutes, hours, days, weeks, or even months over-analyzing a situation; trying to put the pieces together, justifying what could’ve, would’ve happened… or you can just leave the pieces on the floor and move on.” ~Tupac Shakur
Yes or No? Maybe

The reversed Five of Cups as:
…an action?

• Forgive
• Start a gratitude journal
• Take a break from your relationship

 
…a place in your house?

• The cabinet

• Luggage storage

…a place in your city?

• The airport
• A pub with friends

• The suburbs

​
…a place in the world?

• The United States
• Russia
• The United Kingdom

 
…something to eat?

• Dried fruit
• Crackers and peanut butter

 
…something to clean?

• The area directly in front of you

 
…where to find the missing item?

• In front of you

 
…a color? White, brown
 
…a movie theme? Letting go; forgiveness

• Thor
• Zootopia
• Moonlight

 
…a new career?

• Dishwasher
• Delivery driver
• Flight attendant

 
The Five of Cups reversed
Before any card: Letting go of (card)
After any card: forgiveness; acceptance; better days ahead

Read more about the reversed Five of Cups in Applied Tarot Reversed.

I had a great weekend on Whidbey Island. I got some writing and reading done, soaked my muscle aches away in a hot tub, and refreshed my will to live. But while I was away I learned our state would be going into lockdown again immediately upon my return. You're welcome, State. I feel responsible for that.
So after a refreshing weekend, why am I so blue about it?

The Five of Cups is this blue-ness. It could be regret or grief about something that happened in the past, or a mild and temporary depression about something that is occurring at present.

But the card is also a reminder to look for the good. In classic decks, a forlorn person stares at three spilled cups, but he need only to turn around and see that two cups still remain upright. In my interpretation, Santa is sad because the cups in front of him are overturned. He's not seeing that his elves have created entire place settings just behind him. What a miserable boss he is right now.

I should also be grateful for the weekend I had - so what if I need to stay home now? I got away before it all happened! I'm pretty lucky to have gotten away when I did, and I should enjoy that feeling.​

If we imagine pulling cup cards in succession, it is highly likely that the laziness we felt during the four of cups turned into a deep regret about our inactivity.

That's the five of cups. It is the regret or grief about something that happened in the past. However, it also reminds us to look for the good. In classic decks, a forlorn person stares at three overturned cups, but he need only to turn around and see that two still remain upright.
The five of cups is an instruction to lift your chin up and look around you, there may be no need for this much despair.

Questions answered by Five of Cups:
Who? Someone with a lot of regret. 
What? Disappointment
Where? Behind you
When? The last week of October; 5 years ago; 5 units of time from now
Why? with loss comes change
Yes or No? No

Five of Cups
Before any card: Disappointment in (card)
After any card: Grief, regret, sadness
 
The Five of Cups as:
...an action?

• Look for the good
• Start a gratitude journal
• Change something

 
...a place in your house?

• The mantel

• The photos

...a place in your city?

• The river
• A bridge
• Your favorite restaurant needs your business

 
...a place in the world?

• Germany
• Japan
• Indonesia

 
...something to eat?

• Ice Cream
• Nuts

 
...something to clean?

• The area behind you

 
...where to find the missing item?

• Where you made your last mistake

...a color? black, grey
 
...a movie theme? disappointment

• Inside Out
• Marriage Story
• The Fifth Element

 
...a new career?

• Isolating hospitality work, such as a closing bartender, hotel auditor, or night nurse
• Counselor

Five of Cups combinations
With Magician: A miserable person does not realize they have the tools needed to recover.
With Knight of Wands: (before 5) a bold and fearless person dives into something they later regret, or (after 5) a sad person takes a chance on a new adventure.
With Two of Cups: Two people are feeling a loss. (2 before 5) Going through a divorce, or (5 before 2) Divorce brings you closer to your ex - you are better as friends.
With Six of Swords: The transition through grief is a terrible journey, but the right one. A journey is difficult but short.
With Nine of Pentacles: You've done things you regret to make it to the top. It is time to look back and repair the damage.