How To Ask A Guy Out Over Text

Updated March 26, 2024by Regain Editorial Team

Asking a guy out is nerve-wracking. Mustering the courage to actually walk up to someone and blurt out, "Do you want to get a cup of coffee sometime?" may be too much to even consider. You may be tempted to just let go of talking to him altogether just because you are afraid he will say no. But what if he says yes? Before you decide to walk away and let a potentially fun night slip you by, read ahead. Maybe, you’ll find some courage if you ask him how over text, instead of in person.

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Asking a guy out can feel overwhelming

Asking someone out

Asking someone to go out with you is no easy task, including how to ask a girl out. But there are numerous ways to do it, and this article will offer some suggestions. The exact phrasing is entirely up to you, as is the weight you assign to it. If you want to see someone in a simple, casual setting, you might ask him to a movie or coffee for conversation. Alternatively, you may want something that inspires a deeper connection. In this case, you might request a date involving dinner or a show. You may even ask if he wants to go on a date that lasts several hours, depending on how confident you feel. The date you suggest most likely will depend on how familiar you are with the person you are asking out and how intense you want the date to be. 

Also, consider their personality, wants, and needs when you are formulating your date plan. Some men love humor and humorous interactions and might prefer a silly or playful request for a fun date. Others may be more serious and want to be asked out in a way that denotes sincere feelings or deep interest. As much as possible, learn what type of date will resonate with your guy, and plan to ask him out and suggest accordingly. Figure out what he is interested in, whether it be talking or something more engaging and fun. If you still need ideas, consider the following tips for asking a guy out over text:

Be direct

While it may take a little courage on your part, avoid beating around the bush or trying to play it safe and cool as friends. Instead of trying to hint that you want to go out, try being direct and to the point. For example, you can say something as simple as, "Hey. I've enjoyed spending time with you at work. Do you want to get a drink sometime this weekend?" This is casual and simple but straight-forward enough not to leave room for error.

Tailor your phrasing to him

When you ask a guy out over text, try to make it as personal as possible. Text can feel distant and impersonal, so you want to make sure you craft a message that is as unique to your guy as possible; otherwise, it can feel like a canned response that you sent out randomly.

Leave room to get out

Asking someone out always puts you at risk of getting a "no." Ensure that the person you are asking has a safe and simple way of letting you down if that is what he wants. You want to avoid putting him in a situation where he doesn’t feel comfortable or obligated to say “yes”.  You can do this by inviting him to a casual date, such as a musical festival, or by leaving your question open-ended.

An open-ended request to go out with you might look a bit like this: "Are you busy this weekend?" If the guy does not want to go on a date, a simple "Yes" will close down the conversation quickly. You can try again later, or, after a second or third turn-down, you will recognize a pattern. While you are waiting and wondering, look to the next opportunity.

Choose a common interest

If you both enjoy role-playing games (RPG), you can ask him to be your plus one at your next tabletop RPG meeting with friends next weekend. If you know that he loves your favorite band and you see that they are coming to town, shoot him a quick screenshot of the date and venue, along with a simple, "You free?"

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Use inside jokes to your advantage

If the two of you have spent time talking and laughing over something together, use that as a window into asking him out. If you could not stop laughing over how cheesy a movie is, you can say, "I know how much you loved ___. Want to be horrified by the sequel together this weekend?" This is a low-key, low-pressure date, as well as a low-key and low-pressure way to ask someone out on a date.

When you don't get a definitive "yes"

Sometimes, you may ask a friend out for a drink, movie, or coffee and you will not get a definite "no" to the first text, but you won't get a definite "yes," either. Try not to get discouraged. You probably do not take it personally when your friend says they are too busy to hang out, so try to do the same with the guy you asked out over text. Of course, it might be awkward when there is no clear answer and you might be afraid or nervous. As much as it might hurt your pride, the best thing to do is try again. You do not want to venture into the territory of someone who cannot take a hint, but it is possible a guy didn't get your message. Maybe he had pressing matters to attend to and failed to respond, or just was unsure what to say. In any case, trying one more time will give you the closure (or window) that you need to move forward in either direction or will give the guy one more chance to take you up on your offer of a date.

Sometimes, you won't get a response at all. Not even texting back a “Hey.” Although it isn't quite the same as ghosting, some men prefer to stay silent rather than face the awkward nature of turning someone down. If this is the case, you can wait for a few hours or even a day or two before reaching out again. If, after a second attempt, you are still staring at a blank message, it is clear that he is not interested. Feel free to remove him from your mind and phone and move on. Try talking to someone else, be patient, and see what happens. While it may be embarrassing and disappointing, do your best to let it go and open yourself up to other potential love interests. You are a precious human being and there are many people who deserve your time. 

When not to ask a guy out

Although the idea that women should not ask men out is antiquated and rooted in sexist stereotypes, there are instances when you should avoid asking a guy out. These have little to do with being female, though, and have far more to do with reading cues and establishing connections. To avoid unnecessary heartache or rejection, here are some signs that tell you when not to ask him out:

You have no prior history

Asking a guy out when you have no prior history or connection is most likely going to make you both feel awkward and uncomfortable. Even if you met someone online, you should try to establish some amount of rapport first. No matter how you met the guy, you want to ensure you have chemistry before asking him out on a first date, to grab a drink for example. If you get along well after communicating for a few days or weeks, asking him out is likely to be a great idea with the right words. If, however, you merely saw a picture or hung out with mutual friends, and you immediately leap to, "Do you want to go out with me?" you may come across as being a bit too forward. Aggressiveness is a trait that many people may find unpleasant.

There are no signs

If you do not feel connected with a guy, and it feels like pulling teeth when you try to talk, the spark isn't there. Play it cool and do not try to force it by asking him out. When your conversations regularly devolve into uncomfortable silences, or you can never quite figure out what to say, do not ask him out! No matter how attractive you might find him, if you cannot carry on a conversation in-person or over text, you are unlikely to do so in person effectively. Hang in there and look for the next guy.

Furthermore, even if you can hold a conversation, you may notice he is not openly interested in you. Paying attention to his body language will clue you in to how he feels about you. Does he make eye contact often when you talk in person? Does he give you his undivided attention or pay the same amount of attention to you as everyone else? Does he respond quickly and make romantic hints when the two of you are texting? Does he try to keep a text conversation going or does he only respond in curt, short answers? If he doesn’t seem to have much of fun time with you already, then you aren’t going to enjoy going for a coffee, movie, or drink together.

You are desperate for connection

You don’t want to sound desperate when you ask a guy out as this can have the opposite effect that you want. People who sense desperation may lose interest in you quickly, or worse, they may use that desperation to manipulate and use you throughout the relationship.

Remember that no one can make you feel fulfilled or whole, this is a feeling and developmental milestone that you find within yourself – not necessarily in others. If you want to ask someone out because you feel bored, lonely, or afraid of being alone for an upcoming holiday, take a step back and take your hands away from your keyboard. Asking someone out when you are feeling sad and vulnerable is dangerous for a few reasons. The most important of which is your emotional safety. If he says yes, you might feel excited and wonderful for a moment, but if your relationship starts to go awry, you might be right back where you started. If he says no, you are being wounded when you are already in an emotional, vulnerable state. Avoid asking a guy out when you're feeling sad, emotional, or vulnerable, and wait until you are in a strong, healthy headspace.

Asking a guy out over text

Asking a guy out over text is a simple, effective way to ask someone out without a lot of pressure. All you need to do is type out your question and hit send. Texting has replaced phone calls for the most part and is one of the most common ways people communicate today. It is not only far more convenient than waiting to ask him in real life, but it is also an easier way of asking someone out for those who are a bit shy. 

If you are still a bit unsure or nervous of how to start the subject, here are a few tips to keep in mind when asking a guy out over text:

  • Be direct. 
  • Suggest a specific activity and particular time to meet so you do not have to think of an activity later.
  • Do not pressure him. Just ask him out casually and make it seem like it is not a big deal. 
  • Respect him if he turns you down the first time. Don’t keep asking again and again or beg him to reconsider.
  • Look up sample texts online if you’re struggling to find the best wording or phrasing.

Far from being a cowardly act, asking a guy out over text is in keeping with using the most used means of communication while allowing both of you to maintain your dignity.

Getty/Luis Alvarez
Asking a guy out can feel overwhelming

Seeking professional guidance

Asking someone out requires some amount of confidence and courage, especially if the person you ask does not respond or say yes. This can be incredibly discouraging and affect your self-esteem. While finding that special someone is important for many people, developing a strong sense of self-respect and appreciation is vital for your mental health. A therapist can help you work through negative thought patterns and behaviors that are interrupting your ability to enjoy life independently of another person. 

Finding an in-person therapist can be difficult, especially if you live in a rural location, have transportation issues, or are limited by finances. Fortunately, online therapy is available to help you and is supported by research to be equally effective as in-person therapy in helping people navigate through life’s difficult moments. If you feel as though you cannot muster either the confidence or the courage to reach out to someone you like, it may be time to speak with an online therapist or relationship expert. A therapist can help you sort out why your confidence and courage levels are low and can help you find ways to increase your self-confidence and inner strength. 

Takeaway

Asking someone out can feel complicated. However, this article laid out some easy steps for you and the payoff can be worth the potential for pain and embarrassment. One way to ask someone out that relieves some of the pressure is to text them, as it allows you the time and space to craft a carefully thought-out message while giving them the ability to do the same. Asking a guy out does not have to be a chore, nor does it have to be a long, drawn-out process. For a simple, straightforward way to ask someone out, look no further than your phone and corresponding keyboard, and ask away.

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