- Send a greeting text and exchange a few messages back and forth before asking.
- Keep your ask simple, direct, and clear, such as "Are you interested in going out with me?" or suggest an activity for a date.
- Once you send your text, give him a day or two to respond. Then, it's OK to check in if you still haven't heard anything.
Starting the Conversation
Send a greeting text. Try breaking the ice before you ask him out. Send him a simple greeting to get the conversation started. If you haven't talked to him before, remind him who you are and how you met. Say you've been excited to talk to him again. If you have talked before, just greet him the same way you would any other time. People can't always respond to texts right away, so if your first text is you asking him out, you'll start to freak out if he doesn't respond quickly. Talking for a while first helps ensure that he is paying attention to his phone. If you have him talking already, there's a better chance that he'll respond positively to you asking him out. If you ask him out without any warning, he might be caught off guard and say no. For example, text him, “Hey Josh, this is Pete. That party was crazy last weekend. I'm glad we got to meet.” It's simple, but way more effective than texting, “Hey, what's up?”
Pay attention to his interest in the conversation. Text back and forth with him for a while to see how the conversation goes. If he constantly gives short answers or takes a long time in between, he may not be interested in you. You don't want to go straight to asking him out without having an idea whether or not he will say yes. Find the balance between asking him out immediately and waiting so long that the conversation dwindles. If he responds well to four or five texts back and forth, take it as a good sign to go ahead and ask him. Even if he doesn't seem that interested, it's okay to be bold and ask him out anyway. Just be prepared for a possible rejection.
Flirt and see how he responds. As you are texting, begin to send messages that are a bit flirtier than standard conversation. If he responds by flirting back, it's a good sign that he may be interested in going out. If he seems to ignore your flirting or responds negatively, avoid asking him out. For example, text him, “It's a bummer that I'm sitting at home alone. I'd much rather be snuggled up next to you.” If he says, “We could make that happen,” he probably likes you.
Ask him out if he seems interested in you. If your conversation is going well and he responds to your flirting, it's time to move forward with your mission. Don't get too worried about what he will say. Type out the text, check it over, and send it without hesitating. Say, “Dylan, I like you. Would you be interested in going on a date with me this weekend?”
Crafting the Message
Keep your text simple. When you like someone, it's easy to overthink what you are going to say to him. If you type out a long message and ask him out in the middle of it, he may miss your question. Keep the message short and to the point. Send a text that only includes you asking him out. Don't ramble by saying, “I've been thinking about what I could do this weekend because I'm getting bored being home all the time. Would you want to go out? I know there isn't that much to do but I thought that we could have fun together. Anyway, I'm not even sure….” You might want to ask out a guy from school. A teenage guy is more likely to respond to a simple text than to one where you ramble a lot. Text him something like, “Would you want to go out this weekend?” If you want to ask out a coworker, say, “We never get much time to talk one-on-one at work. Would you want to grab a drink when we clock out tomorrow?”
Ask him out directly. You may be tempted to beat around the bush, or mention going out in a vague way that he could miss. When you text him, say that you want to go out with him and ask him if he would be interested in doing that. It's important that he knows you are asking him out. For example, don't say, “I haven't dated much recently and you seem like you haven't either. Maybe we would be able to do something together. That might be pretty cool.” Say, “Are you interested in going out with me?” This is especially important when you are asking a guy out who you are already friends with. It's important to make sure they know you want to go out romantically. Say, “I know we hang out a lot, but would you want to go to Orion's party with me as my date?”
Ask him out to do something specific. When you ask someone out, it's not all that effective to say, “Do you want to go out sometime?” There is no specific timeline or activity involved. Think of something cool you could do together and ask him to do that. Also offer a couple of times that would work well for you. For example, tell him about a party you are going to over the weekend and ask if he wants to go with you. Ask him if he wants to try the new Italian restaurant near your house on Wednesday. The possibilities are endless, and he may say no to the thing you suggest. Asking him to do something specific is still better than asking him “out” in general. This is important when you are asking a guy you just met. Asking to make specific plans will help you find out what they like to do on a date. Say, “I'm a pretty big hockey fan, and I have tickets to the game this weekend. Do you want to be my date?”
Use proper grammar and full sentences. Even with smartphones, it's common for people to abbreviate words and use hard to understand slang. When you ask a guy out, make sure to write complete sentences that make sense. It's a turnoff to see something that looks like confusing gibberish. For example, don't text, “Ay, thot we could hang tmrw. Watcha gonna b doin?” Write, “I was thinking we could go out tomorrow. Would you be available?” Double check your text before you hit send to make sure you didn't accidentally misspell something. Auto-correct can make a message confusing if you don't check over it before you send it.
Waiting for His Reply
Give him time to answer. Texting is not always on a strict time table, which can be good and bad. After you ask him out, wait for him to text you back. If you start to send another text apologizing or asking him if he is thinking, don't send that text. Be patient and give him time to think and send you a response. If you've been talking for a while and he doesn't respond right away, it may be his way of saying no, but don't assume this immediately.
Occupy yourself while you wait to hear from him. If he doesn't respond right away to you asking him out, don't start panicking. Go find something to do while you wait. Staring at your phone or checking it every two minutes will drive you crazy. Set the ringer and find something to occupy your mind. Go for a run, take a shower, turn on Netflix, pull out a book, or work on a hobby. As long as you find something to keep your mind busy, you'll be better off.
Check in with him if you don't hear from him. Sometimes people don't respond to texts, or phones mess up and texts don't get to their destination. If you have waited a while, it's okay to check to make sure he received your message. There's not an exact time when you should text him again. Most of the time if you haven't heard from him within one day, it's okay to text him to check in.
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