8 Ways To Ask Someone Out Over Text: Expert Tips And Tricks

In today’s world, knowing how to ask someone out by text is just as key as doing it in person. Texting is quick and easy and is a big part of how we date today. Pay attention to how you say things, when you send the message, and what you invite them to. This helps increase your chances of a yes.

How To Ask Someone Out Over Text: 8 Expert Tips

Ask Someone Out Over Text

Start with a compliment

Starting your message with a real compliment sets a friendly tone and immediately grabs their attention. Compliments make people feel good and nicely show you’re interested. When you write your message, pick qualities that stand out to you about the person, like creativity, humour, or kindness.

This makes your message feel more personal and powerful. Also, a good compliment shows you notice more than the obvious things about them. Just be sure your compliment is specific and honest. Generic or over-the-top praise can come off as insincere and might not help you much.

Break the ice with an opening message

When you text someone for the first time to ask them out, keep it simple and accurate to who you are. A good idea is to bring up something you both shared or laughed about before. This shows you remember your moments together and makes your text unique. Be clear and friendly without going overboard. Asking about their day or mentioning something recent can be a good start. This way, you show you care and respect their time, which might lead to a nice date.

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Be direct

Start by making contact and showing you’re interested. Then, be direct when you ask them out by text. This keeps things clear and shows confidence, which is appealing. Say clearly that it’s a date. For example, text: “I’ve enjoyed our talks and would love to take you out for dinner. Are you free this weekend?” This directness shows you respect their time and sets the tone for a meaningful interaction. Being upfront helps avoid misunderstandings and builds a real connection.

Keep it light and casual

Why not keep it light and easy when texting someone to go out? It helps keep things fun and stress-free for both of you. By staying friendly and relaxed, you show confidence and real interest without coming on too strong.

Suggest a specific activity or date

asking someone by text

When asking someone by text, it’s best to be clear and show interest. Suggest a specific activity or date. This shows you’ve thought about it and helps the other person decide.

For example, instead of saying, ‘Want to hang out sometime?’ try ‘How about we check out the new Italian restaurant downtown this Friday evening?’ You’re more likely to get a yes by explaining what and when.

Follow up with a confirmation

Once your date agrees to your plan, quickly confirm the details. This shows interest and ensures both of you know what’s happening. You can keep it simple and friendly, like this: ‘Great! So, we’re set for coffee this Friday at 5 PM at Brew Cafe. I’m looking forward to it!’ This way, you’re clear about the plans, and the excitement keeps going.

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Adjust your approach depending on your relationship with the person

asking someone to hang out

Knowing how well you know someone can shape how you ask them to hang out. If they’re a close friend, keep it fun and casual. You can bring up old memories or jokes that only you two get. But be more straightforward if you don’t know them well or usually talk formally. Maybe suggest a specific event you both might like. Adjusting your message to fit your relationship makes it more thoughtful and can make them more likely to say yes.

Prepare for a negative response or rejection

Rejection can be tough, but it’s part of dating. When you ask someone out over text, be ready for any response. If it’s a no, be polite and move on. This keeps things friendly, which is good for the future.


In short, asking someone out by text should be done with care and sincerity. It helps to compliment them personally, talk about things you’ve both enjoyed together and be clear about your plans. Being upfront about the date being a date helps avoid any confusion. These tips help you show your interest clearly and warmly, making it more likely that you’ll connect on a deeper level through your messages.

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