Simply asking “Are you free Wednesday or Thursday?” gives options, while still being direct. This will show your date that you respect their time, but can still handle making plans. Asking your date if they’d prefer to go out on a weeknight or weekend is also a great way to show that you’re flexible and want to see them on a day that works best for their schedule.
Ask your date “Would you rather have a relaxing night or get a little adventurous?” or “Would you rather we have an indoor or outdoor date?” Their answer will point you in the right direction for your planning. Don’t be too specific when giving your date options. Keep some of your plans as an element of surprise.
Some restaurants don’t take reservations, and some activities won’t require tickets. If this is the case, it’s important that you come up with a backup plan for your date just in case your initial plans don’t pan out.
Make two dinner reservations at nearby restaurants – one at 6pm and one at 6:30, for example. If you happen to be running late for your first reservation, you’ll have another reservation at a restaurant that’s nearby. This will make a great impression on your date, as it will be obvious that you’ve thought this date through.
For example, if you’re planning on going hiking, give your date a heads up to wear sneakers and comfortable clothing. High heels and hiking aren’t a good time. If you plan on going to an opera, tell your date to have fun getting dressed up for a romantic night on the town. If they’re underdressed for something like the opera, they may feel uncomfortable, resulting in them not enjoying the date.
Instead of picking an actual location, offering to take a walk or go for a scenic drive is a great option to spend more time with your date. Your date may offer for you to come back to their place – that’s perfectly fine! However, it’s important to let your date make that suggestion, otherwise you may come off a bit pushy.
Choosing the movies for a date isn’t a bad idea, it’s just not the perfect idea. Putting some creativity into your plans will show your date that you’ve made an effort to show them a great time. Movies can be fun if you go to a local film festival, or go see a cult classic at a local theater. If you’re totally set on going to the movies, make it an interesting experience.
Take a cooking class together. Cooking together can be fun and delicious, so look up local cooking classes in your neighborhood. Go on a mini-tour of restaurants and eat a different course at each one. This is a great way to turn dinner into a fun date night adventure. Start with appetizers at one restaurant, get dinner at another, and end the night at an amazing dessert shop. Try out food trucks in your neighborhood. Instead of the traditional restaurant experience, check out the local food trucks in your city. This is a fun way to learn more about your neighborhoods and communities while eating delicious food.
Go bungee jumping, try rock-climbing, or hit the water for some kayaking. These are super adventurous dates that will never be forgotten. If your date is up for a fun time that’s not too extreme, try mini golf and go-karts.
Make sure your date doesn’t feel the pressure to be good at any of these things. Emphasize that these activities are all for fun. [8] X Research source If your date enjoys the arts but doesn’t want to actually participate in an artsy activity, try going to an art gallery or a concert. Pick an activity that will still allow the two of you to interact.
If your date wants to unwind, bring a blanket and a bottle of wine for stargazing in the park. This will make for a nice and relaxing evening while still giving you a chance to get to know each other. Bring a telescope if you have access to one so that the two of you can see all of the stars. Plan a lazy Sunday brunch date instead of Friday night dinner. This takes away the pressure of a fancy dinner date.
If you’re going out on a fancier date, break out your favorite dress and heels, or your favorite blazer. If you’re going on a fun, adventurous date, wear your go-to jeans, your favorite boots or sneakers, and a cute shirt or jacket. Wearing clothes you love will make you feel more comfortable. [10] X Research source
Of course, things happen in life, and you could end up running behind schedule. If this is the case, give your date a quick call or text to apologize for running late, and give them an honest timeframe of when they should expect you. Confirm the time of your date earlier in the day. This will ensure that the two of you are on the same page, and your date will appreciate that you are confirming plans.
Compliment them on something they’re wearing or how they look, and be genuine. Instead of saying “You look nice,” say “You look beautiful. The color red looks amazing on you!” Being specific with your compliments will show them that you’re paying attention. Don’t go overboard with the compliments, but make an effort to show your date that you notice the effort they put into getting ready for the date. [12] X Research source
Don’t show off how much you’re paying for the date. It may come off like you’re showing off or bragging, so it’s best to be more discreet when paying the bill. If your date involves an activity where tipping is involved, leave a good tip (15%-20%). This will impress your date. If your date seems bothered by you paying, let them know that you’re more than happy to foot the bill. Express that you invited them out and you want this date to be your treat.
Ask what kind of date they’d like to go on next. If they’re unsure, give them options again. For example, ask “Would you like to do something adventurous next weekend? I know of some amazing hiking trails and mountain climbing spots. " (You can pick your own activities, of course). Or if you don’t want to go the adventurous route, say “I’d love to see you again next week. Are you free to grab lunch or dinner?” This shows them that you’re flexible to their schedule, and they’ll appreciate you giving the options.
If your date keeps their distance while saying goodbye, or seems in a rush, these are signs that they’re not interested in a goodnight kiss. Some people tend to move slower than others when it comes to intimacy, so this does not necessarily mean that your date doesn’t like you. A first kiss is normally brief and tongue-free, as this shows your date that you like and respect them. If they initiate further intimacy, you can follow their lead. [15] X Research source
