Someone please help me out. Was Lester's girlfriend that same one that he met at Orlando's in season one?

Yes, the very same. Shardenne was actually DeAngelo's girlfriend for a little while, until she dumped him when one of her friends was killed at a Barksdale crew party. This led her to help the police catch Barksdale, which led to her introduction to Cool Lester Smooth.

who wouldn't wear her big coke-bottle glasses and was therefore useless as a witness. Love bloomed when Lester bought her contacts.