The way I read it, you can, for example, fly the day flight late in the day, wait for legal night time conditions, then fly back to your original departure location. If the times and distances of each flight are adequate then the requirements are met.
My $0.02,
yep, that's how I did it, my instructor made me plan it VFR first, after we reviewed the flight plan, he said "so, busy tonight? in a hurry to get home?", I told him "Nope, what's up?" and he asked me to tell hime the time for nautical twilight. And then he told me after looking at my flight time, we would take off and fly simulated IFR direct (but of course, I was given vectors to land at a airport off the flight path for "weather", and told to fly to a third airport under VFR to land and execute a departure.
We arrived at my original destination under VFR (after reporting my delay), we shot three VFR approaches, and then we requested a full stop and taxi to the run-up area, and take off again and immediately shoot three night landings. Then we landed and got a burger while he grilled me on emergency procedures in the aircraft I was going to fly for my solo cross-country.
After that we went into flight planning, I filed a return IFR flight plan with approaches at two airfields enroute. And of course the biggie approach on return home. Best 8 hours of instruction I ever paid for. Funnest "out & back" ever. Note, the only reason and way we could do it all was because I already had a RW Instrument ticket, so although I still needed him on board as a CFII, we only crunched it because I already knew the procedures.
Whole day cost me like $1200 between the aircraft and instruction. But invaluable.