I love the rooftop at Jakes. I think it has the best outdoor dining atmosphere in Tyler (only appetizers on the roof), however I haven't just loved a meal there in a long time. When we moved to Tyler 8-9 years ago, Jakes was my favorite restaurant in town. However, personally think it has gone downhill since then. Is it still good? Yes. Is it great? In my opinion, no. It is definitely more upscale than Villa, and it is more expensive than Villa. However, Jakes makes a great martini. We still go to Jakes every couple of months when the weather is decent, but it is usually just to meet some friends on the roof for after dinner drinks. The roof does have heaters, but even with those I wouldn't go this time of year. If I'm paying $45 for a steak, it needs to be a great steak, and I haven't had a great steak there in forever.
Ricks is kind of the same for me. Ricks doesn't have the roof, but it does have the courtyard which has fun live music on occasion. For a romantic/special occasion, Ricks usually has the piano playing by the bar which is nice. Again, like Jakes, Ricks will be a bit pricey, and I just don't think its worth it (it's good, not great). On a side note, Ricks Au Jue / French Dip sandwich is amazing! I wouldn't order that for an anniversary dinner, but its a pretty great lunch.
For my anniversary, we always consider Villa, Ricks, Jakes, Currents, and Bernards. If you don't mind a really long drive, 4 Winds is good. Some people love Kiepersol. I've never been as having to wear a coat and tie to a dinner is a deal breaker for me, but for a special occasion it might be worth it. Also, Jack Ryans in Kilgore is pretty decent.