Leo wants and needs to be the center of attention. Taurus likes to choose where to go. This duo can work as long as Taurus chooses a place where Leo can be the focus of events. Blending into the crowd will not please ego-driven Leo. Choose activities where the talents of Leo are on display, or where he can at least dress up.
For Leo to successfully choose an activity that will suit Taurus, he needs to consider carefully her past choices and choose accordingly. Otherwise, Taurus is going to spend the evening picking apart the activity, the people and Leo himself. Taurus is a very opinionated sign and there is no stopping the bull once it sees red.
For a simple dinner and a movie date, the Taurus should choose where to dine. Then Taurus should choose what movie to see. As long as Leo is the center of attention to Taurus, this arrangement will work fine. Once Leo gets bored however, all bets are off.
At that point, finding Leo will be the biggest challenge to Taurus.
Leo is extravagant. Taurus is cheap. Where most signs may be miserly with their own money, Taurus is cheap with everyone's money. She will not be impressed with lavish gifts and expensive nights out.
Leo loves to shop and spend. He doesn't understand that Taurus really wants to stay home and watch a DVD instead of going out so that people can admire her beauty. While the relationship is new, Leo will go along with whatever Taurus wants. As the relationship develops, Leo will assert his lion side and demand that they go out. He can expect Taurus to gripe, even though he pays for everything.
Should the Leo in question be female, she should expect that she is going to be the one opening her wallet as the relationship progresses. If they split the check, Taurus will get out his calculator and get it down to the nearest penny.
These two set the bedroom ablaze with fighting. Leo is exuberant and that tends to annoy the more sedate Taurus. Both want to have their way to such a degree that most of the passion goes to arguing rather than lovemaking. It can work if they can take turns getting their own way.
Long Term Outlook
The long-term outlook for Leo and Taurus is for a constant struggle and battle of the wills. If they can come to mutual agreements about money and prestige, it can work. For it to work, both Leo and Taurus are going to have to be open, honest and understanding about their partner's and their own idiosyncrasies.