How To Ask A Guy Out Over Text

Updated November 15, 2022 by ReGain Editorial Team

Asking a guy out is nerve-wracking. Mustering the courage actually to walk up to someone and blurt out, "Do you want to get a cup of coffee sometime?" can be too much even to consider. This article goes over some pointer on “What is the best way to ask a guy out via a text message?

Asking A Guy Out Can Be Scary

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. If you want something a bit more intense, you might request a date involving dinner or a show. If you are confident and interested, you might request a date with several hours. The type of date you mention will depend on how familiar you are with the person you are asking out.

When you ask someone to go out, you should consider their personality, wants, and needs. Some guys love humor and humorous interactions and might prefer a silly or playful request for a fun date. Some guys are a bit 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, and suggest based off of that. Below are some tips for asking a guy out over text in this article.

Ways To Ask A Guy Out Over Text

1) Be Direct

Nobody benefits from you 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 direct enough not to leave room for error.

2) 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 you sent out randomly.

3) 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 safe, or make him feel like he has to say “Yes.” You can do this by inviting someone 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.

4) Choose A Common Interest

If you both enjoy role-playing games, 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?"

5) 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."

You will ask someone like a friend out for a drink, movie, or coffee in some cases, and you will not get a definite "no" to the first text, but you won't get a definite "yes," either. Of course, if this happens, it might be awkward and you might be afraid or nervous, but in these cases, 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 and will give the guy one more chance to take you up on your offer of a date.

In some cases, 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. Keep after it. Try talking to someone else, be patient, and see what happens. You may experience fear at the idea of trying again, but keep talking to people. The trouble only begins when you give up entirely. Hang in there!

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 women, though, and have far more to do with reading cues and establishing connections. To avoid unnecessary heartache or rejection, do not ask a guy out when:

1) You Have No Prior History

Asking a guy you have never really connected with is likely 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 some good chemistry before asking him out on a first date to grab a drink for example. If you get along well after talking back and forth 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, "Wanna go out with me?" you may come across as being a bit too forward. That's a trait that men and women both find unpleasant.

2) The Signs Aren't There

If you don't 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 don’t try to force it by asking him out. If 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 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, that doesn’t necessarily sound like a guy is 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 actually 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.

Asking A Guy Out Can Be Scary

3) 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. Guys who sense desperation may lose interest in you quickly, or worse, they may use that desperation to manipulate and use you throughout the relationship.

Furthermore, no one can make you feel fulfilled or whole. 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 or making a big deal of it. All you have 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.  Far from being a cowardly act, asking a guy out over text is in keeping with using the most commonly used means of communication while allowing both of you to maintain your dignity.

If you’re 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 as no one like it when you beat around the bush.
  • Suggest a specific activity and particular time to meet so you don’t have to think of an activity later.
  • Don’t pressure him. Just ask him out casually and don’t make a big deal of it.
  • The most important thing to keep in mind is to 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.

Asking someone out requires some amount of confidence and courage. 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 a therapist or a relationship expert (such as those found at Relationship Hero). A therapist can help you sort out why your confidence and courage levels are low and can help you find ways to increase your feelings.

Asking someone out is never quite easy or simple even though this article laid out some easy steps, but the payoff can be worth the potential for pain and embarrassment. One way to ask someone out that relieves some of the pressure typically associated with asking someone out 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. As described in this article, asking a guy out doesn't 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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