Best Boulder crag for evening session?

So I am totally new to the boulder area and am completely overwhelmed by the amount of climbing in the area (In a good way!) My buddy wants to go climb for a couple hours after work and I really can't decide on where to go. Could anyone help me out? I'm coming off a pretty serious spine injury and can't really climb above a 5.5 right now. I'd love a 2 pitch 5.5 or below that's close to the road. Thanks!

Gonna assume you're sticking with sport? ;)

The Dome has a couple 2 pitch 5.6/5.7s right next to the road. East Slab is a good one at 5.6.

The best sub-5.6 climbs in Boulder IMO are on the flatirons but that's not right next to the road obviously and if you pitch them out would probably take a bit long for after work.

I'd suggest the First Flatironette or Front Porch formation. The hikes to these can be done in 20-25min on mellow trails, the routes are fun and under 5.4, and there will not be crowds. Both formations could be done in 2 pitches, although 3 is the standard. The climbing tends to go quickly and these are doable after work. Cool views from the summits. Expect long runouts, but solid belay anchors can be found.

"Freeway" on the 2nd Flatiron. Many routes on the SW face of Wind Tower.

Just about any Flatiron East face will be fun and within the grade range you're looking for. As mentioned above the only downside is that it may entail a pretty lengthy approach.

Wind Tower in Eldo holds some options in that range. I hope your recovery continues smoothly.

Apart from the established routes on the first Elephant Buttress, the rest is really easy climbing. Single pitch.