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Dude Asks Latest Articles

How To Ask Someone Out Over Text?

Written by:
Reviewed by: Paul McCoy
How To Ask Someone Out Over Text?

Asking someone out can be nerve-wracking, but now with technology, you have the option to do it over text. While it might seem simpler than face to face, there are still some rules you need to follow to ensure your message comes across the way you intend it to. In this article, we’ll take you through some tips on how to ask someone out over text, so you can nail the message and hopefully score that date. Whether you’re new to texting or just unsure of how to proceed, we’ve got you covered. So, let’s get started!

1. Get to Know the Person First: How to Build a Connection Through Texting

How to Ask Someone Out Over Text?

Asking someone out over text can be a nervous experience, especially if you don’t know the person well. Building a connection with someone through texting can help alleviate some of that nervousness and make the process smoother when it comes to asking them out. Here are some tips on how to build a connection with someone through texting:

1. Start with small talk: This can open the door to a conversation that leads to more in-depth topics. Ask about their hobbies, interests, or what they enjoy doing in their free time. By doing this, you’ll be able to get to know what makes them tick and what they’re passionate about.

2. Respond appropriately and promptly: Don’t leave the person hanging. Text them back if you’re free, and respond in a timely manner. This shows that you’re interested and care about their time.

3. Share your own interests: Talk about what you enjoy doing or your hobbies. This can help the other person see if they have anything in common with you, which builds rapport and can lead to a more fun and interesting conversation.

In summary, building a connection with someone over text involves starting with small talk, responding appropriately and promptly, and sharing your own interests. By doing this, you’ll be able to make the person feel that they know you better and can trust you, which is an important foundation for asking them out.

2. Tips to Make a Great First Impression: Starting the Conversation

Your first text message can make or break your chances of getting that first date. That’s why it’s crucial to start strong and make a great first impression. Here are some tips to help you get started.

Be Genuine and Authentic

Don’t try to be someone you’re not. Authenticity is key to building a connection through text. Be genuine and show your personality. Don’t be afraid to be a little vulnerable or share some personal details about yourself. This will make the other person feel more comfortable and open to connecting with you.

Keep It Simple and Short

When it comes to texting, less is more. Keep your first text message simple and short. Avoid sending long, rambling messages that might overwhelm the other person. A simple greeting and an invitation to chat is a good way to start. You could say something like, “Hey there! I’ve enjoyed talking to you in class. Would you like to grab coffee sometime this week?”

Use Humor and Emojis

Humor is a great way to break the ice and make a good first impression. If you can make the other person laugh, it shows that you’re not taking yourself too seriously and that you’re fun to be around. Emojis are also a great way to inject some personality and playfulness into your text messages. Just be careful not to overdo it.

Avoid Compliments or Flirting Right Away

While it’s important to show your interest in the other person, it’s best to avoid compliments or flirting right away. This can come across as insincere or even creepy. Instead, focus on building a connection and getting to know the other person better. Save the compliments and flirting for when you’ve had a chance to establish some rapport.

3. What to Say and Not to Say: Crafting the Perfect Text Message

Crafting the perfect text message can be nerve-wracking, especially if you’re asking someone out. You want to make a good impression but also not come on too strong. Here are some dos and don’ts to help you craft the perfect text message.


  • Be direct and confident: State your intentions clearly and confidently. Don’t beat around the bush or make excuses.
  • Use humor: Humor is a great way to break the ice and show your personality. Use a funny meme or joke to lighten the mood.
  • Include a compliment: Compliment the person’s interests or personality. This shows that you’ve been paying attention and are genuinely interested in them.
  • Give them options: Give the person options for the date, time, and location. This shows that you’re flexible and considerate of their schedule.


  • Don’t be too vague: Don’t say “want to hang out sometime?” Be specific about your intentions and what you want to do on the date.
  • Don’t use cheesy pick-up lines: Pick-up lines can come off as insincere or cringy. Stick to being genuine and direct.
  • Don’t send multiple messages: Sending multiple messages can come off as desperate or pushy. Give them time to respond and respect their decision.
  • Don’t use excessive emojis: Emojis are great for showing your personality, but too many can be overwhelming. Stick to a few to convey your message and tone.

Crafting the perfect text message can be tricky, but by following these do’s and don’ts, you’ll be sure to make a great impression and increase your chances of getting a positive response.

4. How to Take the Next Step: Making Plans for a Date

Taking the next step after a successful conversation via text can be intimidating. However, it’s essential to seize the momentum and ask the person out on a date. Here’s how you can make plans for a date via text smoothly and confidently.

Be Specific in Your Invitation

It’s essential to be clear and concise when making plans. Instead of a general invitation to hang out, suggest a specific activity or event. It will make the person feel that you’ve put some thought and effort into wanting to spend time with them.

For example, you could say something like: “I was thinking about checking out a new art exhibit this weekend. Would you like to come with me?” Or, “I know a fantastic burger place downtown. How about we grab dinner on Friday night?”

Know Their Availability

Before making plans, take their schedule into account. Inquiring about their availability will show that you’re respectful of their time and commitments. It will also help avoid the awkwardness of suggesting a date when the person is unavailable.

Examples of messages you could send include: “Are you free on Saturday around 6 pm?” or “When are you available to meet up this week? I’d love to plan something.”

Offer Options

Offering a few different date options will give the person the freedom to choose a time and day that works best for them. It also shows that you’re flexible and willing to work around their schedule.

Try something like: “I was thinking of going to the movies on Sunday or grabbing drinks on Thursday after work. Which day works better for you?”

By following these tips, you’ll make asking someone out over text a positive and stress-free experience. Remember to be genuine, personable, and respectful throughout the conversation, and you’ll be surprised how smooth the conversation flows.

5. Dealing with Rejection: How to Handle a No-Response or a Negative Answer


As much as we want to succeed in asking someone out through text, there are times when the answer we receive is not what we expected. Whether it’s a no-response or a negative answer, handling rejection gracefully is crucial for our own well-being and future relationships.

Don’t take it personally

The first thing to do when dealing with rejection is to understand that it’s not always about you. Sometimes, the person may simply not be interested or may have other priorities at the moment. It’s important to remember that rejection is not a reflection of your own worth or value as a person.

Stay positive

Try not to dwell on the rejection for too long. Remember that there are plenty of other people out there and keep a positive attitude. It’s important not to let one rejection bring down your self-esteem or confidence in approaching others.

Move on respectfully

If you receive a no-response or negative answer, it’s important to respect the other person’s decision and move on. Avoid pleading or pressuring them to change their mind or sending multiple messages. Instead, thank them for their time and let them know that you understand and respect their decision.

In summary, dealing with rejection is never easy but it’s a part of the dating process. Remember to stay positive, not take it personally, and move on respectfully. With the right attitude, you can bounce back and keep trying until you find the right person.

People Also Ask

1. How do you start a conversation with a crush over text?

To start a conversation, make sure to initiate with a thoughtful and attention-grabbing message. Avoid using generic openers or sending a one-word greeting. It is better to personalize the message and add a compliment to show genuine interest.

2. When is the best time to ask someone out over text?

Choosing the right moment to ask someone out over text is crucial. Wait until you have had enough conversation to gauge whether they are interested in dating you. Make sure the timing is right, and the person is not preoccupied with work or personal tasks.

3. How do you ask someone out over text without being awkward?

When asking someone out over text, be clear and straightforward while also being sincere and casual. Avoid using cheesy or over-the-top language, as it may come across as uncomfortable or awkward. Keep it simple, but still acknowledge and appreciate the person’s interests.

4. Is it okay to ask someone out over text?

Yes, it is okay to ask someone out over text. However, it is important to communicate your intentions clearly and positively and avoid coming across as insincere. Be prepared to receive a reply in any form, as emotions do not always transfer well through technology.

5. What are some creative ways to ask someone out over text?

You can make your invitation stand out by being creative and thoughtful. You might use a play on words, send a meme, or create a fun and engaging digital image. Consider making it personal and tailored to your date’s interests so that they feel special and appreciated.


Asking someone out over text takes some courage and tact, but it can be a comfortable and convenient way to initiate a potential relationship. Be clear and sincere with your intentions, avoid being overly scripted or generic, and keep the conversation light and casual. Remember, it is only a text, and it is okay to get turned down or receive no response!

John Alexander

John Alexander

Digital Content Producer/EditorNovice 👶
Living in the vibrant city of Seattle, Washington, I thrive as a Digital Content Producer where the intersection of technology and creativity energizes me every day. With a passion for storytelling and an insatiable curiosity for innovation, I craft content that engages, informs, and inspires. My experience extends beyond content creation; I also excel in the role of editor, meticulously refining digital narratives and overseeing the editorial process to ensure optimal quality and coherence. This dual expertise allows me to not only create compelling content but also to guide and collaborate with fellow creators to elevate their work. Fueled by coffee, indie music, and the endless rain that defines my beloved city, I find the perfect backdrop here in Seattle to produce digital narratives that resonate across global audiences. When I'm not immersed in the digital realm, you can find me exploring Seattle's eclectic neighborhoods or attending local tech and creative events, always seeking new sources of inspiration for my next project.

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