How to "freestyle" like this?

There is a lot of wisdom in this statement.
The term ‘less is more’ comes to mind here.

Unfortunately, in my experience, most beginning Bass, and especially guitar players, want to be in the spotlight and be running fills, solos, etc all over the fretboard too often.

When learning to improvise/freestyle there is a term that is not stressed enough and that is PHRASING which means to pick a spot for a solo, walking Bass line, arpeggio etc. and make it short and sweet and not take over the whole song.

The last three words are so true and cannot be overemphasized.

For me no rhythm on Bass = disaster, and failure, for a song.
A Bass player with no rhythm is not serving the tune, as they say, and will cause the song to fall apart in short order.

In one of the jam sessions I attend there was one fellow that refused to practice, even though he had the lead sheets for the music we would be playing that night, and had no sense of rhythm at all. Without fail every song just fell apart when he played because of his lack of rhythm. His attitude was that he was there to have fun and socialize and he did not need to practice. In the end he was asked to leave the group.

IMHO @chordsykat has the right approach in the beginning.

I love jamming with others and by doing what @chordsykat is talking about you should be able to take a lead sheet and just play the chord roots in a short period of time. You just need to to know where the root note of the chord is on the fretboard. Then it all comes down to the beat and rhythm.
For the beat just follow the drummers lead because you do not want to screw him up.

Bass and Drums have to work together.

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I find the best way to start this journey is to load a drum machine app on your phone, plug it into the aux port on the amp, and pick a pattern, and listen to the drums.

I usually start with one note at a time, I pick one that sounds like it goes with the drums, and once I have the first note, the others suggest themselves. And pretty soon I have a riff going. Then I refine it. I generally don’t have the progressions down right the first times through.

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Sounds familiar.
Practicing with at least a simple drum backing track is so much more enjoyable.
Kinda makes you feel like you are at a jam session playing along with others.

I do the same thing only using my Zoom B1XFour or lately creating drum patterns and a 12 bar chord progression pattern in Reaper and using them as a backing track.

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Practice Dorian 30 minutes a day for 2 weeks…