No, you don’t have to get used to it! Don’t wear heels if you don’t feel comfortable in them. I personally only wear heels to weddings (and my high school graduation). The right shidduch will not insist that you wear something that hurts you and leaves lasting damage.
If you really want to try again, however, I recommend a short, chunky heel as opposed to a tall, spindly one. This type of shoe will give your feet the necessary support. Alternatively, you can wear espadrilles or wedges, which I find to be just as comfortable as flats.
I happen to be dating someone who is approximately the same height as me, but if your shidduch is taller, you can experiment with different types of shoes. Payless has some great styles, or if you’re like me and enjoy shopping online, try zappos.com and 6pm.com. You can also join a shoe of the month club, such as JustFab.