How to Set up a Date Successfully

Asking the Person Out

Get to know more about them. Even if you just met the person, take a few moments to get to know a little about them. If you already know them, talk to them to find out more. The more you know about them the easier it will be for you to ask them out and the easier it will be for you to set up a date successfully. Ask what they like to do for fun. For example, you might say, “So what types of things do you enjoy doing for fun?” Ask about hobbies and interests. You could try saying, “What are some of the things that you do in your spare time?”

Practice your approach. You will feel much more confident and comfortable asking the person out on a date if you have practiced your approach. Rehearse what you will say and how you will say it in order to set up your date successfully. Stand in your bathroom mirror and practice what you will say to ask the person out on a date. For example, you might look in the mirror and say, “Hey, Frank! I was wondering if you might like to go out some time?” If you need to, then write down what you want to say and rehearse it with a friend.

Be confident. Approaching your potential date with confidence will make it more likely that they will want to go out on a date with you. It will also help set the tone for a successful date. Take a deep breath and remind yourself that you can successfully get a date with this person. For example, you might say to yourself, “I can do this. I can successfully set this date up.” Put a smile on your face, hold your head up, and feel confident about yourself.

Work on building your self-esteem. You will have an easier time feeling confident and working up the courage to ask someone out if you feel good about yourself. Take pride in your good qualities, and set a few positive, realistic goals for yourself. You might try some of the following: Practice positive self talk. If you find yourself thinking or saying negative things about yourself, gently redirect yourself to something positive. For example, instead of, “I still have so much left to do. I'm so disorganized,” tell yourself, “Wow, I finally finished that huge job on my to-do list! Way to go!” Take care of your physical health by exercising, eating right, and meditating. Focus on doing things that you enjoy and are good at. Keep your goals and expectations for yourself and your life realistic. Don't compare yourself to other people.

Ask them out on a date. Once you have learned more about them and built up your confidence, you need to go ahead and ask them out. Tell them you would like to go out sometime and then talk about the details to set up the date successfully. For example, you could say, “Deborah, I'd love to go out with you sometime! When might be a good time for you?” Or you might try, “I really like spending time with you. Would you like to go on a date with me?” You could even say, “There's a great new restaurant that opened up around the corner. I know how you love Italian, would you like to go?”

Planning a Great Date

Get the other person's input. You can set up a date successfully if you know what the other person likes to do or might enjoy doing on a date. Talk to them to get some specific ideas about how to make this date successful. For example, you could ask, “Is there something special you would like to do? Or is there anything you absolutely don't want to do?” Or you might even ask, “So, what would be your idea of a great date? What would you do? Where would you go?” Reader Poll: We asked 1029 wikiHow readers about which first date they’d like to go on the most, and only 8% said going rock climbing. [Take Poll] So, suggesting a more casual activity, like grabbing dinner or seeing a show, might be more fun for your date.

Decide when to go out. Although you may want to go out on the date as soon as they say 'yes', slow down and plan when you will go out. Your date will be more successful if you figure out the right day and time to go out on the date. Talk to your date about their schedule. Find out when would be a good day and time for the date. For example, you could ask, “When will you be free over the next couple of days?” Also find out what time of day will be best for the date. Although dates are often at night, a day date might work out better.

Pick a place to go. The location of your date can have a big impact on how successful the date is or even if the person agrees to go. You can ask your date where they would like to go or you can think about places your date might enjoy going on your own. You might say, “Is there anywhere in particular you would like to go on our date?” Consider fun places like an amusement park, county fair, or the zoo. Think about some place romantic like a floral garden, cozy restaurant, or live play.

Make reservations. You may decide to go somewhere on your date that requires tickets (like the movies, a live show, or special event) or a reservation (like a fancy restaurant). If so, you can set the date up successfully if you go ahead and make reservations or purchase your tickets. Doing this in advance takes away the stress of doing it later and risking ruining the date by not being able to get tickets. Also, if you have to change the plans for the date because you couldn't get tickets or reservations, you will have time to do so.

Work out transportation. Take the time to think about how you and your date will get to the location(s). Especially if you are planning on going to more than one place, work out transportation for the date. If you drive and are picking your date up, do you need to get gas or clean out your vehicle? Will you be using public transportation? If so, do you have bus, train, or subway schedules? Do you know what car services are available? If you aren't picking your date up, how will they get there? How will they get home? If your date activities are within walking distance, have you checked the weather report for that day?

Check-in with the person. Unless it's a surprise, let your date know what you have planned and make sure everything works for them. Checking-in with the person will help you be confident that you have successfully set the date up. This will give your date the opportunity to let you know if anything has changed or if they don't like anything that you have planned. You might say, “Hey, I was thinking we could go ice skating Friday afternoon around 4 PM and then have hot chocolate. I can pick you up.” Try to check-in with them a couple of days before the date if you don't already talk to them on a regular basis.

Having a Successful Date

Be prepared. The best way to have a successful date is to plan in advance. Think about what tone you want the date to have, how you want your date to feel, as well as the logistics of the date. For example, make sure you have enough money and have thought about transportation, tips, and other fees. Think about the weather. Do you need to bring an umbrella or ask your date to bring a jacket? Think about things you want to talk about and whether you want the date to be more romantic, fun, exciting, etc. You might also think up a few conversation starters or interesting questions before your date, so it will be easy to keep the conversation going smoothly.

Be friendly and respectful. Make an effort to show your date that you respect them, care about their feelings, and enjoy their company. Here are a few simple things you can try: Pay attention to your date. Make it clear that your focus is on them, not yourself. Don't try too hard to impress your date – i.e., don't brag about yourself, your possessions, your job, and so on. If you drop off your date at their place, walk them to their door. If you drove to the date separately, call or text your date to make sure they got home safely.

Present yourself well. For your date to be successful, you should not only look nice, but act respectful as well. Take the time to put extra effort into your appearance and your actions. Wear a special outfit or do something a little different with your hair. If you'll be working before your date, give yourself time to go home, shower, and change clothes, so you'll be in more of a "date" mindset. Act respectfully. Say 'please' and 'thank you' as well as 'excuse me' when it's appropriate. Show confidence by smiling, holding your head up, looking your date in the eye, and talking in a clear voice.

Talk to your date. Even if you are super nervous, you should make conversation during the date. Talking gives you a chance to know more about each other and to make your date successful. So put your phone on vibrate and talk to your date. Ask questions to get your date to talk about themselves. For example, you could ask, “What's been the most interesting day you've ever had?” Before the date, think of topics that you could talk about like: sports, hobbies, favorite movies, or music. Give your date a thoughtful compliment. Keep it simple – you could say something like, “You look really nice tonight!” or “I saw the painting you posted on Facebook. You're so talented!” Don't overdo the compliments, or your date may feel uncomfortable.

Make sure your date feels included. If you're hanging out with other people, or if you encounter someone you know while you're out, it's important to make sure that your date doesn't feel left out. #*Take time to introduce your date to everyone. Make sure to include your date in conversations. Don't spend a lot of time talking with your friends about things your date is unfamiliar with. E.g., don't go on about things that you and your friends did together, or make your date feel excluded with a lot of inside jokes.

Be flexible. No date goes exactly as planned. The weather changes unexpectedly, cars break down, and other small disasters can occur that can throw your date off track. If you are able to go with the flow and make changes to the plan as needed, then your date will be more successful. Have a back-up plan in case you can't go through with your date as planned. For example, have an alternative restaurant in mind or another activity planned as a backup. Try to have extra money in case of an unexpected event.