I feel like you are doing this for the wrong reasons. You want a date because you want to have a good time with somebody, or because you need somebody and want to be married at your target age of 32? I just feel like you are getting way ahead of yourself here.
Dating is mostly about having fun and enjoying company with one another. You never start dating somebody with the intention of marrying that person, do you? I think you should just focus on that and within due time you will work your way up to more serious relationship level stuff.
I gotta tell you though, not having a girlfriend by this period in your life is going to put you behind the curve a bit. There is alot of stuff that can be learned from past relationships that will help you in the future. It's not impossible, but it's not helping. The sooner you get yourself out there, the better.
Just put your feet one step ahead of the other in front of you. This girl seems cute and likes you at the pharmacy. If she's working, stop by and talk to her. And if you don't know what to talk about, talk about anything. I'm sure if you talk about the weather it might feel like you are just talking to an adult, but you guys went to the same high school right? That would be a start. Give it a few times, and if she still seems interested, give her your number to chat or text sometime. You don't have to just concentrate on her but you have to be patient.
Waking up next to a beautiful girl,
Step outside and say hello to my beautiful world.