First of all, let me thank all y'all who offered advice on what I should do. I couldn't have felt confident about my choices without you.
Let me just say that I had a great time and the waiter was very accomidating. I ordered an 8 oz filet (the smallest portion of beef they had) and promptly cut it in half and gave half to my boyfriend (who is skinny as a rail). I got to HAND PICK my veggies (from the salad bar) and I "guesstimated" about a cup of broccoli, which the chef steamed for me. AND, I know I probably shouldn't have, but I had about a cup of salad with a couple of cherry tomatoes and a few onion slices with fat-free dressing on the side. I dipped my fork into the dressing and then took a bite of my salad, which worked well.
I felt like Sally on "When Harry Met Sally." The evening was great, the food was great and I felt like a pro ordering.
Thanks you guys.