Last Updated 23.04.2022
13 min read

Tips On How To Ask Someone Out Over Text Successfully

Alan Schin (he/him/his) is the Chief Editor at Taimi. He wears several hats daily as a writer, editor, blogger, and content contributor. He began his university studies as a Psychology student but found his passion in Advanced Communication Studies. Alan loves having the opportunity to write and help our content team shine. According to Alan, his education helps him to understand the dynamics behind dating and socialization better. When he isn’t busy with Taimi, Alan works on his first novel, a sci-fi thriller, and creates works of art in his ceramics studio.

Asking someone you like out can be very nerve-wracking. Choosing to do that over text can take a lot of the stress away and help you feel a lot more comfortable and confident. In order to achieve that though, you need to have a plan ready so you know what to say every part of the way.

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    Making plans in advance about your texts and the date itself is very important. Knowing what you wish to say and how will make you less stressed, even in case the other person responds to you negatively. Here are some great tips and tricks on how to ask someone out over text and make sure it is a success.

    Is Asking Someone Out Over Text a Good Idea?

    There are both positives and negatives when it comes to asking someone out over a text message. It is important that you weigh both sides and then decide which option would be the best for you.

    First of all, asking someone to go out with you over text can be the perfect solution for every introvert who is too shy to ask that in person. Texts give you more control over any conversation and can help you express yourself a lot easier. At the same time though, they don't allow you to use your body language to show your true emotions and intentions.

    Most introverts would have a very hard time saying what's on their mind with someone looking into their eyes, so this gives them the opportunity to not forget anything they wanted to say.

    That being said, text messages might not help you show your emotions in the way they should. For example, when you have a verbal conversation with someone, you are easily able to switch your tone of voice and focus your attention on certain words and emotions you wish to convey. The only real way of doing that through texts is by using emojis to show your emotions in every sentence.

    Overall, asking someone over a text can be a little tricky as they might not find it as personal as if you had told them in person. This is always a chance you have to take if you feel like sending a text is the best option for you and that's okay. This will not undermine the fun you will have on the actual date so choose what makes you feel more comfortable and confident.

    Start by Giving Them a Compliment

    To kick off a text conversation on the right foot, you can give the other person a compliment! Just like in real life, you can approach someone and break the proverbial ice by complimenting them on their appearance, lifestyle, hobbies, and anything else listed on their social media or dating app profile. You'll feel less pressure and more confidence in opening a conversation if you start by sending an honest and well-intended compliment to the person you're into.

    People receive text messages from people who are apparently into them all the time - by genuinely making a point of someone's facial features, body language, style of writing, or any other info you find online, you'll be at a distinct advantage. Most people really are surprised when someone texts them simply to tell them they like the smile on their profile pics - and that's just one example of what you can do!

    They'll be far more interested in following up on your message with compliments of their own and feel comfortable talking to you moving forward. Even if you're unsure of whether you're into someone, compliments can be a start of a fun time together and you can suggest online dating down the line if you vibe with the person on the other end.

    Make Sure You are Close Before Asking Them Out

    One of the things you will have to work on is making sure that you have spent some time getting to know them before you ask them out. This is important for a lot of different reasons and it will help you increase your chances of actually turning this date into a success.

    First and foremost, you will know more about the things they like to do and everything you have in common. The more the things that connect you, the higher the possibility of them seeing you in a romantic way. You will be able to do fun things together and they know they won't get bored at all during this date.

    In addition to that, you will also have the chance to see what you truly like in this person. When you know someone for a short amount of time, it is possible that you will confuse liking their appearance with their personality. Talking to them and even becoming friends will help you learn more about them and see exactly which qualities you love about them.

    All these factors will make asking them out a lot easier as they will already see you on a friendly level. Sometimes, it takes a little time getting to know them better before they even consider you as a potential relationship. Therefore, make sure that you spend some time getting to know them and be on friendly terms before asking them the big question.

    Be Specific About This Being a Date

    You should try and find out how the person feels sooner rather than later in terms of dating you. Most people appreciate knowing whether they're actually talking to someone who is romantically interested in them or just wants to be friends. As your text conversations go on, try and be specific about the fact that you're inviting the other person on a date.

    Don't wait too long until making it clear and talk to them about how you feel. Be friendly, be polite, and be affectionate without going overboard and professing your love to them. After all, you've been sending messages back and forth for a few weeks and you want to move things forward slowly. If the person isn't interested in seeing you (yet), don't take it too personally and go through hard feelings. They might just be reserved, introverted, or have had bad experiences in the past with text message invitations.

    Express your interest in meeting them or talking to them on the phone for the first time to see whether you click with one another. And hey, you yourself might come to realize that this isn't the right thing for you right now and choose a less romantic course of action, such as becoming very good friends with the person on the other end.

    Let Them Choose an Activity They Enjoy

    One of the things you need to plan in advance is who will focus on planning the activity of the date and where it will take place. Some people like to be caught off guard and others prefer to be able to choose the location and activity by themselves. You need to openly communicate this with the other person and see what their idea is.

    After you have told them you wish to go on a date, ask them when they are next available so you start making arrangements. Ask them openly whether they would prefer they choose what you will do on the date or if they would like you to surprise them.

    This is exactly why getting to know them in advance is important. Since you will know the things they like and dislike, you will be able to go ahead and make arrangements based on these facts. Even if they choose the location themselves, you can still keep a few aces up your sleeve and surprise them with something unexpected. This gives you a higher likelihood of the date being a success and them wanting to go on more dates with you.

    Make Plans About the Date

    Going into more specifics, you should plan certain things about the date apart from the location. Figure out which dates the other person is available and whether you need to make reservations for the date.

    It's never a good idea to wait until the last minute to make arrangements, especially when you have decided to go somewhere that needs booking in advance. For example, if your randevouz is to take place over a weekend, you should not wait until Friday to make arrangements for it.

    You probably want everything to be perfect and making arrangements in advance will help you feel so much better and more confident. Waiting for the last minute will make you anxious and you might end up forgetting to book something important only to realize that you forgot during the date.

    "xLove is so unpredictable. Sometimes you'll know a man for years and then one day, boom! Suddenly you see him in a different way. And other times, it's that first date, that first moment. That's what makes it so great." - Sarrah Dessen

    Be Prepared in Case This Doesn't Go the Way You Imagined

    When it comes to asking someone out on a date, there are always two possible outcomes. One, they might be excited to go out on a date with you and see you as more than a friend, and two, they might not want to go out initially, or at all.

    These are two possibilities which you cannot affect and you need to be prepared for as they are both just as likely to happen, so there is no reason for you to worry excessively over it. If they answer that they wish to go out with you for a coffee date then great, it is your que to start making preparations for it.

    If they have decided they would rather stay friends, you also need to be prepared to follow certain steps in order to maintain the relationship between you. They are certainly free to choose whichever option of the two and you will have to be able to react in a reasonable way, even if it hurts you.

    Give Them Space and Time to Think

    When you get rejected by someone you have feelings for, it might be difficult to think straight. This is why keeping a distance for some time is really good for both of you. The fact that you are asking them over text allows you to not show whether this truly hurt you or not and you are able to collect your thoughts without being angry or sad in their presence.

    This might be a great opportunity for you to give the other person some time to think as well. They might not have expected you to ask them out or they might be afraid that this revelation could ruin the friendship between you. It is also possible that they don't know how to approach you after this and they might be worried you won't be able to look at them as just a friend again.

    All these worries are normal and part of this situation. It is also just as likely for them to need some time to actually realize they would like to give this a try and go on a date. In order to reach that conclusion though, they might need some time to consider all possibilities and think about where this relationship could go.

    Therefore, the best thing you can do is give them some time, even up to a week to think and see how they react when the two of you interact again. This will also play a role in your actions towards them and help you see whether this was a good move or not.

    Don't Make Them Feel Guilty About Anything

    Just because you’re texting and considering a possible date doesn’t mean that the person on the other end owes you anything. Don’t resort to guilt-tripping or gaslighting when things don’t go your way. It’s a sign of an adult and a responsible individual to manage their emotions and show compassion and understanding. If the person you like isn’t interested in dating you – that’s okay.

    Look at the positives and consider the fact that you know up front that they’re not a romantic interest for you. Forget the concept of outright acceptance of all of your ideas – each relationship starts (or doesn’t start) differently. Whether you’re texting through the phone, a web app, or some other way, try to understand their reluctance as something that’s not your fault. They might be afraid of meeting people they’ve met online or they may have gone through a traumatic dating experience recently.

    Tell them that you understand their answer and that you are always available for coffee or a casual talk down the line. Waiting for a more positive response from them may also help you recontextualize and better understand your emotions toward them, which can help you a bunch when you decide that you want to date someone.

    Consider Whether Staying Friends Would be Okay

    Receiving that faithful text message with a negative response to your date proposal can lead to two things. You can either stop texting the person and end your conversation politely, for mutual understanding or keep talking to one another and become friends.

    The latter however is tricky to pull off if one of you is in love with the other. There are many text ideas out there for you to use if you want to become friends with someone you’ve been courting. You can tell them about the things you share in common, how you admire their lifestyle and would like to go out or introduce them to your friend group, etc. Make sure however that you are prepared to become friends with someone you’re interested in romantically.

    It’s a tricky thing to pull off, so you may want to wait and talk about the topic openly. Make it clear that your message is clear and that the person doesn’t get a sense of you trying to sneakily court them when they’re off guard. This will alleviate any worry either of you may have about the other and lead you to a promise of a potential friendship that can last for years if things start on the right note.

    Asking Someone Out Over Text and Making it a Success

    When you ask someone out over a text message, there is always the possibility that they will decline your advances and prefer for the two of you to stay friends. At the same time, this might be a great success and you might go on the best date of your life.

    No matter the outcome, you won't know until you try, so make sure you put your fears aside and let them know how you feel. This might help you finally start that new relationship or understand where you need to shift your priorities.

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