Original dates are the most memorable. Think a little outside the box when planning dates. This helps to avoid repeat dates (which can often remind people of old flames). Plan unusual things to do that will engage your date and promote conversation.
Take your date to do something athletic or interactive. Have a video game tournament or take her bowling, ice skating or to a roller rink. If you're having an evening date, hit a pool bar for drinks and a few games. For outdoorsy activities, consider renting bikes, horseback riding or kayaking. Karaoke is a great ice breaker, as well. Spend the night belting out your favorite songs---you may even want to try a few duets.
Take your date window shopping. Grab coffee to go and visit an upscale mall. Spend the day playing dress-up and trying on things you can't afford. Use this opportunity to get inside your date's head and discuss dreams and plans for the future.
Find a themed dinner show to enjoy. You can try murder mystery dinner shows, or themes such as Arabian nights or Medieval times. This creates a great ice breaker or conversation topic over dinner and is likely to be a date that you'll remember for a long time.
Hunt for a cool dinner recipe that neither of you have tried yet, with a corresponding dessert. Doing the shopping together for the ingredients is half the fun. Work together to create your meal, and set the table with candles to create a more romantic vibe. Pick a movie that you'll both enjoy and watch it after you've cleaned up. Trying new recipes brings something exciting to your dinner---even if you're not eating out---and breaks up the monotony.
Try Something New
Try new foods and types of restaurants, instead of something familiar. Consider dining out at a fondue restaurant or a churrascaria (a Brazilian steakhouse usually set up buffet-style). Step out of your comfort zone and try a hip Indian place or a Thai noodle bar. Your date will appreciate your willingness to try something new.