How to ask someone out on a date: A practical guide

When it comes to asking someone out, we understand why the idea might make you nervous. Even when you can almost palpably feel your connection and have liked them for some time, you still get caught up in how they’ll take it if you can’t find the right way to ask.

You may wonder how to ask someone out on a date in a way that’s both respectful and authentic. The answer depends on your relationship, the current context and finding the right timing to explore your respective emotions. But there are some easy ways to boost your chances without having to go over the top.

Let’s explore the best ways to ask someone out, including how to ask for a date, the right things to say, taking stock of the emotional context of the situation, and a look at why we find it so challenging to begin with.

What does asking someone out mean?

In a straightforward sense, asking someone out means suggesting a specific time and place for a romantic date. While it can be as simple as, “Want to go out together some time?” it often includes other contextual aspects of the date, including location, transport, and the expected length of the date.

The number of ways of how to ask someone out are almost infinite. But why do we ask people out? Because they interest us, because we think we like them, because we want to get to know them, because you have a clear romantic interest… The reasons are almost as endless as the ways.

It’s not about asking someone outright to be your romantic partner, but rather more subtly indicating there’s romantic intention from your end, but you’re not sure how much – or if it’s even sustainable. It’s more about exploring your connection first.

Asking someone out in different situations

When trying to find the best answer to how to ask someone out, context can help show you the right thing to say and also the right medium to say it on.

Asking someone out in person

Research shows that any kind of in-person requests tend to get the most positive answers quicker¹. It also gives you access to a whole range of social aspects like tone, your level of confidence, and body language cues. If you’re figuring out how to ask someone on a date, these aspects can give you extra insights beyond words.

However, getting face-to-face with the person you like isn’t always immediately feasible, or can come across as contrived. It’s a good option if you already know the person reasonably well, see them regularly, and don’t mind the more formal nature of an in-person date proposal.

Asking someone out over text

When you’re looking at how to ask someone out over text it’s not as compelling as in-person, but it does give you the advantage of seeming more casual. It could also help the other person feel less cornered by the question. They can think about it, shape a response, and give you a well-thought-out answer. This is ideal for people you already know but aren’t particularly close with yet.

When texting, it’s important to warm them up a bit first before you ask. Don’t over-craft the message. Keep it simple, clear, and to the point, while possibly including a sweet compliment somewhere. Whatever their answer is, make sure you respond with grace and politeness.

Asking someone out on a dating app

How you can ask someone out and the type of singles you can interact with have grown exponentially since the boom of online dating apps. This has paved the way for a new form of dating etiquette online. It allows you to vet potential matches, get to know people better, control who interacts with you, and partake in dating on your own time.

Transitioning smoothly from an online interaction to a real-life date is often about building rapport and trust over text. But don’t get stuck just communicating over apps. Once you feel like there’s a genuine connection and they’ve signaled some interest in you, the ideal way for how to ask someone out online is to just be kind and upfront. All you want to see is if there’s also chemistry in person.

How might people show non-verbally that they like you and you can ask them out?

To answer this question, we asked one of our eharmony relationship experts:

When you’re looking at how to ask someone out, the best answer can often depend on who that person is to you and what tone you’d like to strike.

Tips for asking someone out

1. Use open-ended questions: When you’re talking to them, remember to ask open-ended questions to keep the conversation flowing until you’re ready to ask.
2. Keep your connection in mind: How you ask can depend on your relationships. How to ask a coworker out, for instance, can be quite different from asking a casual acquaintance.
3. Respect boundaries: Don’t put pressure on people to say yes ,or complain that they’re not getting back to you fast enough. 
4. Rehearse your ask: Try practicing what you’re going to say beforehand.
5. Choose the right vibe: Find the right setting and date activity that matches both your sentiments and interests.
6. Time it right: When to ask someone out is mostly a matter of timing. Wait for a day when they feel relaxed and open.
7. Plan with purpose: Have a good idea of what the date will entail before suggesting it.

How to ask your crush out

• Leverage what you know: This will be different from how to ask a stranger out. Use what you already know about them to your advantage. Suggest something you know they’ll like or surprise them with something you know they’re curious about.
• Make it personal: Try personalizing an invitation if you already have a friendly relationship. For instance, you could put the date request at the end of a short scavenger hunt.
• Start in a group setting: If they’re reluctant to meet one-on-one, you could try involving them in a friendly get-together to get to know them better from there.

Cute ways to ask someone out

• Show that you see them. Find out what their favorite bakery in the area is and have something delivered with a simple note attached. 
• Go unexpected: Pick a date idea that’s completely out of left field but still sounds fun, like an interactive digital exhibit or a rooftop cinema.
• Make the ask feel effortless and fun: To ask out a guy or ask out a girl in a cute way, frame the invitation in a way that feels spontaneous and easygoing. For example, “How about ice cream sometime? You, me, and a cone?”

Creative ways to ask someone out

• Make it uniquely yours: Forget old school or new school ways of how to ask someone out. Instead, find your own message medium. For instance, a message hidden in origami or sending them the pieces of a small jigsaw puzzle with the message as the solution.
• Use playful communication: Say it over text without using words at all. If you have a playful relationship, try just sending them an emoji message to decode. It will help them get more engaged and excited.
• Use context to your advantage. If it’s a snowy day, a nearby festival, or just a movie series they like playing in town, use it as a springboard to hang out together. Then you can use the date itself to confess your feelings. 

If we had to single out the best way to ask someone out, which many of the suggestions have in common, is to start your idea with at the heart of things. Use anything you or your friends know about them to ask them in a way that shows that you see past the superficial – without being too invasive – and want to create unique experiences with them.

What to say to ask someone out

What you say when asking someone out on a date can significantly influence your chances of success and how you’re perceived by the other person. We’ve gathered some examples of what you can say, helping you come across as confident and friendly:

• Remember, how to ask someone out in person is to keep it simple: “It’s been really cool getting to know you today. I’d like to know more if you’re free anytime soon.”
• You could try a few bold ones, like: “Where do I need to book a table to get you to agree to dinner with me?”
• “I can’t stop smiling every time I see you. Care to meet up sometime and test my theory?”
• “If you keep up making me laugh every time we meet, I’m going to go ahead and ask you for a date.”
• Sometimes, a more laid-back approach works, particularly if you’re looking at how to ask someone out over text: “You. Me. Street food tacos. Friday. 7:00?”
• “Would you be open to doing something outside of [work/friendship/group]?”
• “I think I can figure out why I have a crush on you in under an hour? Want to take the challenge and meet up?”
• “Hope this isn’t too forward, but I’d love to take you out sometime. Up for it?”

Why is it so hard to ask someone out?

There are a number of factors at play that can stymie your efforts when figuring out how to ask someone out. However, the star of the show is undoubtedly fear of rejection. We are inherently social beings, so social rejection speaks to our ability to function in groups, damaging our social resilience and sense of belonging². But this isn’t on the person you’re asking out. You’ll have to learn how to overcome your fear of asking someone out on your own journey. One of the best ways to get over rejection is through repetition, maintaining positive self-talk, and breaking down rejections after they occur so you can make sense of them and stop seeing it as an inherent failure of yours.

Another aspect is the status quo bias, which is a smart way academics have found to delineate our fear of upsetting our existing systems(“Status Quo Bias in Decision Making”). Asking for a date may seem small and insignificant, but to the individual, it represents a change: changes to your existing relationship and possible changes to social hierarchies you both belong to. Not all change is a threat, but it reflexively remains a source of concern.

Becoming comfortable with change takes time. Try to reframe transitional times of change as exciting, even if they’re uncertain too. Also, always prepare for the worst outcome while expecting the best, so you can maintain a positive mindset while also practicing mental preparedness.

Social anxiety relates deeply to the first two fears and can be a real obstacle in how to ask someone out in a normal, healthy way. This has far-reaching implications beyond dating. However, practicing limited and mindful communication in dating in conjunction with a variety of self-help techniques and cognitive behavioral therapy has shown profound improvements for many sufferers.³

Other cultural aspects, such as feeling held back by traditional gender roles, can feel deeply ingrained, but not necessarily permanent. In all of these instances where one feels stuck in figuring out how to go out with someone while overcoming these fears, we’d recommend going easy on yourself, moving slowly, communicating openly with potential partners, and considering clinical intervention, if necessary.

How to handle rejection after asking someone out

Our inherent fear of rejection can sometimes make us scared to ask someone out. One of people’s biggest problems is our pattern-seeking brain trying to turn the instances of rejection into universal judgements. You stop thinking, “That person wasn’t interested in dating me,” and it turns into something far more pernicious, like “That person rejecting me proves that I’m undesirable and unlovable.”

If this all seems a bit rash in the context of how to ask someone out, it’s because it very much is. Our brain is constantly leaping to wild conclusions in the name of self-preservation. So the best way to deal with rejection is to surround yourself with all the things that make you feel loved and desired, like your friends, family, and the things you care for.

But the most important person to reconnect with is yourself. Practice self-care, validate your negative emotions, and reconnect to yourself through journaling or alone time. 

Focus on how to ask someone out casually and respectfully

It’s easy to see that modern romance and getting dates, despite all their apparent pitfalls (which are often self-manifested), are all about being active in the process. Before you make your move, you need to do your research on the other person, lay the groundwork for a healthy bond with them, bide your time for the right moment, and finally be bold enough to tell them how you feel.

But if you’re still finding it all a bit daunting or complex, come and meet authentic, compatible singles on eharmony. Get good at interacting with people who interest you and practice how to ask someone out in a single-friendly environment. Then learn how to see slight rejections for the insignificant moments they are and figure out what style works for you when it comes to meeting singles that get you.

Q&A – Expert backed answers to your questions