How to Ask a Friend on a Date

Deciding You're Ready to Ask Your Friend Out

Take a minute to appraise your own feelings. How do you really feel about your friend? Perhaps you’re just interested in getting to know them a little better, or maybe you’ve found that you’re attracted to them and want to get to know them from a different perspective. Feelings are often confusing things. Make sure you’ve sorted out exactly how you feel and what you want before you try taking things to the next level. Even if you’re attracted to your friend, you may decide that it’s advisable to take things slowly and cautiously if the two of you are already close.

Consider whether your friend feels the same way. Think about the kind of “vibes” you get from your friend. Are the two of you close, or do you just hang out with the same group of people? Do they laugh at your jokes and show an interest in what you have to say when you’re talking? Try to gauge your friend’s feeling as accurately as you can. If it’s obvious that there’s no real attraction being reciprocated, it might be best to hold off on asking them out. If they act warmly towards you, however, they may have similar feelings, and might have even hoped you’d ask.

Talk to your other friends about it. If you have another friend that knows the friend in question and you feel comfortable talking to them about the situation, ask their thoughts on how you should proceed. They probably know something you don't know one way or the other, or have unique insights into the matter that might not have occurred to you. Your other friends will eventually find out if you're dating, so don’t make it look like you were keeping it a secret from them. If your other friends learn how you feel, they may subtly talk to the friend you like, facilitating the process. Keep in mind that your other friends are affected by whether or not you start dating. While this shouldn’t necessarily prevent you from asking a friend out, show enough respect to be conscientious about your evolving relationship with that friend and what consequences it might have.

Spend some alone time together. The next time your group of friends is hanging out, look for opportunities to pair up or spend some time alone with the friend that you like. This could be playing a game of pool together, having a thoughtful one-on-one conversation at a party or standing next to each other at a concert. Get comfortable with the idea of being alone with your friend and try to also get a sense of how they feel about it in these moments. If your friend gravitates to you during future hangouts, it’s probably a good sign. Don’t dole out your attention to your friends unfairly. Take an opportunity to spend time alone with your friend if one arises, but don’t make them feel forced to split off and ignore the rest of your company.

Finding the Best Circumstances to Ask Them Out

Keep your expectations in check. Don’t expect too much to happen too soon, if at all. Even if your friend likes you back, they may be reluctant to do anything that might jeopardize the relationship that the two of you currently have. Whatever your friend decides, you should be okay with it. If you get too set on the idea of dating, it may come as a disappointment if your friend declines, which could create distance between the two of you as friends. Learn to take “no” for an answer. If your friend agrees to spend time with you one-on-one but makes it known that they’re uneasy with the dating label, accept their position graciously and plan to find something casual to do. Put whatever misgivings they have about endangering your friendship to rest by assuring them that you’ll remain friends regardless of how things turn out.

Make sure the time is right. You should be taking your friend’s feelings into consideration as well as your own. If they’ve been giving you flirtatious signals, it might be a clue that they’re interested in you and will agree to a date. If they seem disinterested or you’re having trouble reading their feelings, they may be uncomfortable with the idea. Recognizing the appropriate point to ask a friend on a date will most often come down to personal judgment. It’s probably better not to ask your friend out in a group setting where they may feel pressure to respond in a certain way.

Determine the best way to ask. The best way to ask someone on a date in most circumstances is face-to-face. However, since you and your friend already have an established platonic relationship, asking them out directly may be awkward or make them feel pressured. Weigh your options. A friendly phone call might do it, or you could drop the proposition during a text conversation. Your friend will probably be most amenable to the idea of going on a date if it doesn’t feel like a big deal, so don’t make it one. Think about how your friend does most of their communicating and go with their preferred mode. That way nothing feels off when it comes time to broach the subject. EXPERT TIP Cher Gopman Cher Gopman Dating Coach Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post. Cher Gopman Cher Gopman Dating Coach Try asking your friend on a date when you have somewhere that you say you have to be. You can say something like, "I have to run, but I'd love to grab a drink sometime together as a date." This gives them space to think about it and will make it easier for you to ask them out.

Ask in a friendly, relaxed way. Once you’ve determined how you’re going to ask, work the offer naturally into a conversation with your friend, or be collected and up-front about it. The two of you are already friends, so there should be a mutual degree of respect and comfort in place. Frame the question in a way that reinforces that the decision is theirs, and that you want to remain friends either way. It might be easiest to suggest that just the two of you do something together as friends sometime, since this will cause no initial concern of changing the nature of the relationship. If your desire is to continue dating as more than friends, though, make sure you’re displaying your intentions honestly. If your friend declines your offer, smile and carry on in an amiable manner. They will likely be worried about straining the friendship if they turn you down. Make sure that they know you’re still happy to be their friend. It’s possible that the time just wasn’t right, but now that your friend is aware of your feelings they may in time discover that they’re attracted to you as well.

Preserving Your Friendship

Remember that you’re friends. No matter how things progress between you, your friendship is the foundation of your relationship and the most important thing. This thought should feel like a safety net for you when you’re mustering the nerve to ask your friend out. If it’s not what your friend wants or they’re not yet open to the possibility, you’ll have your friendship to fall back on, and you should: a true friend will understand and be there to make sure everything is okay. Even if you start dating and things are going well, don’t forget that they were your friend first. The comfort of that bond will make your connection even stronger. Try to think of your new relationship as a branching outgrowth of your friendship, not a replacement for it. All of your interactions should come from a place of caring and acceptance. There’s no reason for the friendship to suffer simply because you’re trying to build on it.

Try not to neglect your mutual friends. Dating a friend can sometimes cause complications if you tend to hang around the same people. Be upfront with your other friends about the situation and let them know that it won’t alter the friendship of the group. Take particular care not to isolate yourselves when you’re with your mutual friends: this can be easy to do when you first begin to date someone, but it might give the rest of your friends the impression that you’re disinterested in them. Since you began as friends, work on cultivating an environment where you can still spend time together even when you’re involved with someone. Make some time each week for all of your friends to get together. During this time, involve yourself in the group’s activities and discussions, and don’t make it feel like you and the friend you like are separating yourselves from the rest of your friends.

Don’t despair if it doesn’t work out. If your dating efforts aren’t met with success, don’t let it come between you and your friend. You knew to keep your expectations out of the picture, so there’s no need to take it too hard. Not wanting to date may just mean that they value you very highly as a friend, which is a good thing. There’s no harm in liking someone, and you shouldn’t feel awkward or guilty if you tried and things didn’t work out. In the worst case scenario, you can simply go back to being friends. It’s a win-win! You shouldn’t be embarrassed or feel the need to “punish” your friend if things don’t work. Withdrawing from your friend group will make you appear sulky and may send the message that you were only looking to date the person from the beginning. Allowing resentment to build up will take its toll on your friendship, which is precisely what you don’t want to happen.

Enjoy each other’s company. Whether you hit it off on your date or you don’t, take pleasure in being around one another. Starting off as friends means you already know you have common interests, can communicate openly and like spending time together. Look at it as a chance to spend some quality time with the person with no thought to the outcome. Do things that you both enjoy and relish the occasion to make new experiences and memories with the friendship at the heart of your relationship. For a first date, keep things from feeling too serious by suggesting a short hike or picnic outside, a casual dinner at one of your favorite restaurants followed by coffee, or a movie.