Any Plans For The Weekend? How To Ask Someone Out On A Date


Any Plans For The Weekend? How To Ask Someone Out On A Date

The secret to confidently asking someone out on a date is overcoming fear, using the right words, and knowing how to handle rejection. Follow our expert tips.
How to ask someone out

It’s the question that can make even the most confident among us pause.

“How Do You Ask Someone Out?”

The anticipation, the overthinking, and yes, those little butterflies.

You don’t want to come off as desperate or too forward, but you also don’t want to be so vague and wishy-washy that your intentions are unclear. 

As a professional Social Skills Coach with almost two decades of experience helping thousands of socially anxious adults in their romantic pursuits at Jaunty, I’ve encountered a wide range of common mistakes we all make and I’ve learned a few things that can help everyone avoid them.

If you’re not sure what to say, or how to say it – or the big one – when to transition from flirty behavior to the topic of making a date, I’m here to help you!

We’ll delve into the details and show you a more graceful way to approach popping the question, ensuring your intentions are clear without crossing boundaries. Let’s navigate this dance together, striking a balance between showing interest and respectful assertiveness.

How To Ask Someone Out On A Date

Whether you’re asking someone out for your first date, trying to get over a rejection, or starting to date again after a breakup and get back out there, these tips will help you feel more confident and prepared.

1. Build a Connection

Before you ask someone out, it’s important to establish a rapport and build a connection. This doesn’t mean you need to become best friends, but having a conversation or two can help you gauge their interest and make the situation less awkward.

  • Start with a casual conversation about shared interests or experiences.
  • Ask open-ended questions to encourage them to share more about themselves.
  • Listen actively and show genuine interest in their responses.

2. Choose an Appropriate Activity

The reason building a connection is so important that we made it step one is because it allows you to suggest a fun activity that you know they’ll enjoy. This shows that you’ve been paying attention to their likes and interests, which can make your invitation more appealing.

  • If they’ve mentioned a love for coffee, suggest meeting at a local cafe.
  • If they’re a fan of live music, ask if they’d like to go to an upcoming concert.
  • If they enjoy nature, propose a walk or hike in a nearby park.

3. Be Specific

When your sure that your playful flirting has sparked their interest and you’re ready to ask them out, be specific in your proposal. This means mentioning a specific activity, day, and time. Vagueness can lead to confusion and might make the other person feel uneasy.

  • Instead of saying, “Got any plans this weekend?”, say, “Would you like to grab coffee this Saturday at 10 AM?”
  • Being specific also shows that you’ve put thought into the invitation, which can be flattering.
  • If they’re unable to make it at the suggested time but are still interested, they’ll likely propose a different time.

4. Flexibility is Key

While it’s important to be specific, it’s equally important to be flexible and open to the serendipity of life. If the person you’re asking out is interested but unable to make the date or time you suggested, be open to their suggestions for a different time.

  • Showing flexibility can make the other person feel more comfortable and less pressured.
  • It also demonstrates that you’re genuinely interested in spending time with them, not just sticking to your own schedule.
  • Remember, the goal is to spend time together, not to stick to a specific plan.

5. No Pressure

When asking someone out, it’s crucial to make sure they don’t feel pressured or manipulated in any way to say yes. Make it clear that it’s completely okay if they’re not interested or can’t make it.

  • Keep your tone casual and friendly.
  • Reiterate that it’s okay if they can’t make it or if they’re not interested.
  • Pressure can make the situation uncomfortable and might lead to an insincere yes.

How To Ask Someone Out Over Text?

Asking someone out over text can be a great option, especially if you already have a good flirting banter going on. The key is to be specific and clear in your invitation. 

Examples of asking someone out over text

  • Instead of using vague phrases that could be taken as friendly, like “Want to hang?”, be clear about your intention. For example, “I want to take you out for a [fun activity], what time should I pick you up?” 
  • Suggest a specific activity they might enjoy, such as, “I know you love [music genre], There’s a great band playing [time and place]]. Care to join me?”
  • If you’re unsure about their schedule, give them options. Something like, “I’d love to grab coffee with you. Are you free [option A] or [option B]?” This can work wonders to increase your chances.
  • Mention something you’ve talked about before to make it personal: “You mentioned you love [type of food]. How about some dinner and great conversation at [day and time]?”
  • Humor can be a great icebreaker. Consider something playful like, “I promise I’m more fun in person than over text! How about we test that theory over dinner this Friday?”
  • If you’re feeling extra confident, you can shoot your shot with a more direct approach, such as “Very interested in getting to know you better and I’m free Saturday night.”

Remember to give them space and time to think. It’s also important to be prepared for any response. If they say no, let them know that there are no hard feelings, and move on. 

What If You Have Social Anxiety Or You’re Shy?

If you’re shy, the idea of asking anyone out might lead to immediate feelings of social anxiety. However, there are ways to make the process easier. Start by building a connection with the person. Engage them in conversation and get to know them better. Once you feel comfortable, suggest an activity that you both might enjoy. This could be anything from going out to dinner, seeing a movie, or attending a local event.

  • When you’re ready to ask them out, be clear and confident.
  • You can rehearse what you’re going to say beforehand to help ease your nerves.
  • Remember, it’s important not to pressure them into saying yes.
  • Give them the freedom to decide if they’re interested.
  • Make sure to exchange contact information and be clear on the time and place.

What If You’ve Been Rejected In The Past?

Rejection can be tough, but it’s important not to let past experiences or emotional baggage deter you from asking someone out. Start by building your confidence. Remember, everyone faces rejection at some point, and it’s not a reflection of your worth. When you’re ready to ask someone out, do so with confidence but without seeming desperate.

Important Note On Handling Rejection Gracefully

Rejection is a part of life, and it’s possible that the person you ask out will say no. If this happens, it’s important to handle the rejection gracefully.

  • Don’t take it personally.
  • Appreciate them not wasting your time.
  • Handling rejection well shows maturity and respect, which are attractive qualities.
  • Remember, everyone has their own reasons for saying no, and it’s not a reflection of your worth or value. 

Do’s And Don’ts Of Asking Someone Out


  • Do establish a connection before asking someone out.
  • Do suggest an activity that you know they’ll enjoy.
  • Do be specific in your proposal, mentioning a specific activity, day, and time.
  • Do show flexibility if they can’t make the date or time you suggested.
  • Do make sure they don’t feel pressured to say yes.
  • Do handle rejection gracefully if they say no.


  • Don’t ask someone out without having a conversation or two first.
  • Don’t suggest an activity without considering their likes and interests.
  • Don’t be rigid about the date or time, be open to their suggestions.
  • Don’t be vague in your proposal, as this can lead to confusion.
  • Don’t pressure them into saying yes.
  • Don’t take rejection personally.

Don’t Let Dating Anxiety Hold You Back. 

Dating should be an enjoyable experience for both people involved. So relax, be genuine, and let your personality shine through. With the right guidance and tools, you can learn to navigate any social situation with ease and confidence.

That’s where Jaunty comes in.

For over 15 years, we’ve helped guide a wide range of individuals through every kind of goal you can imagine. From business leaders who want to improve their networking skills to shy singles looking for love.

 Elevate Your Social Skills And Grow

At Jaunty, we offer a comprehensive Social Skills Masterclass designed to elevate your social capabilities. This six-week journey dives deep into essential social life skills, including the art of asking someone out. Our course is designed not just as a learning experience, but as a holistic transformation journey. 


Eric Waisman

Eric Waisman

Founding Instructor

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