My computer asks for a key when trying to pair with this speaker.

you can.

How to Connect JBL Flip 4 to Alexa Speaker - Tom's Tek ...

https://tomstek.us > how-to-connect-jbl-flip-4-to-alexa
Jun 29, 2021 - Connect JBL Flip 4 to Alexa Instructions, Step by Step · 1. Find the Alexa App on your Mobile Device · 2. Run the Alexa App · 3. Tap the Hamburger ...

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  How to Pair JBL Flip 4 with Amazon Echo Dot Speakers

  https://tomstek.us > how-to-pair-jbl-flip-4-with-amazon...
  Jul 9, 2021 - How to Pair JBL Flip 4 with Amazon Echo Dot Speakers · 1. Find the Alexa App on your Mobile Device · 2. Run the Alexa App · 3. Tap the Hamburger ...

Try doing default factory settings.
Step 1. Press the "Power" button located on the top center part of your JBL Charge 4 Bluetooth speaker. The speaker will be powered on when the LED backlight under the Power button is lit.
Step 2. Hold down the "Bluetooth" and "Volume Up" buttons at the same time for roughly three seconds. The Volume Up button looks like a plus sign. Additionally, it's important to hold down the "Bluetooth" button in the center of the device next to the Power button, as it's easier to hold down. After three seconds, the LED ring around the Power and Bluetooth buttons will briefly light up before the JBL Charge 4 powers down.
Step 3. Press the "Power" button again to turn the JBL Charge 4 Bluetooth speaker back on. The Charge 4 will instantly turn on in Discovery mode, with the Bluetooth LED blinking on and off, and the speaker making a pinging sound. This confirms that you've successfully reset your JBL Charge 4 to its default factory settings. You'll need to pair or re-pair any devices you want to play audio through the JBL Charge 4 speakers with the device.

unpair jbl speaker in windows 10
then put jbl speaker into pairing mode
then on windows 10 pair speaker in bluetooth settings
then
test speaker to see / hear if it now works

Drivers would be a fair guess. Have you updated macOS to latest versions? If so, I would try JBL's suggestion.

JBL has the Quick Start Manual for the Flip 2 on the product site: http://www.jbl.com/bluetooth-speakers/JBL+FLIP+II.html . Scroll down and expand the Manuals & Downloads section. The link to the manual is the one on the right. The direct link is http://demandware.edgesuite.net/aauj_prd/on/demandware.static/-/Sites-masterCatalog_Harman/default/dw3064f0fb/pdfs/Flip2_QSG_EN.pdf . The pairing feature should be as simple as tapping the Bluetooth icon on the speaker. Then set your laptop to search for a new Bluetooth signal.

I hope this helps.

Cindy Wells

Problem connecting Windows 8.1 pc to JBL Charge bluetooth speaker ...

answers.microsoft.com/.../windows/.../windows8...connecting-windows...

When I try to connect the pc through Bluetooth to the above wireless speaker ... 2) What is the model of the JBL Charge Bluetooth speaker? ..... I am already able to play music from my iPhone 5 on this speaker via Bluetooth with no problems.

Cannot connect JBL Charge Bluetooth - Networking, Internet ...

en.community.dell.com/support.../network...wireless/f/.../t/19525571

Dell
Sep 22, 2013 - 16 posts - ‎11 authors
23 Replies; 16 Subscribers; Postedover 2 years ago ... I'm trying to connect my JBL Charge Speaker bluetooth with my Dell Studio 15 laptop to listen .... I am having the same problem, did you find a fix for this? ... not support audio output, then you need to add a Bluetooth adapter which includes a CD driver.

JBL Charge 2 ' Portable Bluetooth Speaker with USB Charger

www.jbl.com > Wireless > Portable Bluetooth Speakers

JBL
Rating: 4.3 - ‎110 reviews
Most popular JBL Charge 2 wireless portable speaker can charge any devices via USB... You can easily connect Charge 2 to any Bluetooth-enabled device by giving the portable's ..... Charge with proper charger or a USB port form computer.

I guess you only can pair one device at a time

Are they connected or paired now? Make sure you don't have any other device near that may have Bluetooth on. Like a laptop, PC,or tablet. Try forgetting the device, and reconnecting. If this fails make sure your phone isn't on wifi and cellular. If this all fails. I imagine its not the fault of your transmitter, but lies in the fault of your reciever, the JBL flip. Also, is it fully charged and is the speaker holding a charge? I'm a small Bluetooth speaker junkie, and I'm sorry but I am not impressed with these at all. There are much cheaper, and better made out there, than this one.

What model phone? Have you gone to JBLs website for troubleshooting?

Mark
Motorola Support

JBL Link 20 New device set up issue.

I called LVL 2 Tech support at (877) 871-6755 for my set up new device issue. The support person was very helpful and recognized this issue to be very common.

COA 1: I had already tried resetting my speaker using the pin hole button next to the USB power connector on the back. This did nothing as far as I could tell

COA 2: (Best Solution) look for the microphone on/off button under the power on/off button located on the back of the speaker. Press and hold down the microphone button for 10-13 seconds. The lights above the power button will flash a reddish color. This indicates the speaker is reset to factory settings.

Completely close Google Home app and reopen the app. You should notice some options changed. Go through the simple “setup new device” process and it should allow you to get Link 20, Google Assistant, and your home WiFi on the same page.

I am having an additional issue because I’m currently traveling and using hotel WiFi. Because of public WiFi firewalls here, Google doesn’t like it and won’t let me completely finish setup through Google Home app. Once I get home to my personal home WiFi I will complete the factory reset function again. Until then, I have great Bluetooth for music and movies while traveling.

Good luck and hope this helped.
(All the info I just passed on is basically what the Google LVL 2 Tech Support agent talked me through)