How to Transition From Chat Line Dating to Face-to-Face Dating

So, you met someone in the chat lines. They’re funny, smart, and the two of you get along well. It seems like it’s finally time to meet this person face-to-face. But you’re not sure how.

Should you wait for them to ask you out or should you make the first move?

Lucky for you, turning a chat line date into a real one is possible, but requires more effort than just talking. To help you land an actual date, we’ve put together a checklist on what you need to do before making the first move. Let’s get started with how to ask someone out and the do’s and don’ts that you need to be aware of.

What to Do Before Asking Someone Out on a Date

You might think you’re ready to ask someone out on a date, but in reality, you’re not even close. Getting someone to go on an actual date with you isn’t all about asking the question itself, but also about what you do before asking. To increase your chances of getting a “yes” here’s what you should do before you decide to ask someone out from the chat lines to a date.

1. Take the time to get to know each other

I know what you’re thinking — getting to know someone before asking them out on a date might seem contradictory to the purpose of dating itself, which is to allow people to get to know each other and determine whether they’re a good fit or not.

So, should you get to know each other first before starting to date, or should you just go for an actual date and see where it leads you?

If you’re living in the early 19th century, going out on a date with someone you don’t know might work well. But nowadays, going on a date without prior knowledge about each other rarely works, especially if you’re looking for a potential long-term relationship. If anything, going out on a date with a stranger is considered dangerous and suspicious.

Most people also have a hard time agreeing on a date with someone they don’t know well due to the surge of date-rape cases and catfishing in recent times. That being said, taking the time to get to know each other to establish mutual trust will increase your chances of landing a date.

Ultimately, the best time to ask someone out doesn’t depend on how long the two of you have been talking, but on how well you have gotten to know each other — whether that took three days or two weeks.

2. Plan the date

You don’t want to ask someone out and tell them that you haven’t planned anything yet, but you will if they say yes. If anything, it’s a guaranteed way to sabotage your chances of landing a date.

By asking them out and telling them the date ideas you have in mind at the same time, it will make them appreciate the fact that you planned, increasing your chances of getting a positive response.

The first step in planning a date is deciding on a location. How well you know the other person may come in handy in these situations. For example, you have discovered that the person you want to take on a date is fond of nature.

You might want to consider a nice dinner by the ocean. Or perhaps they have mentioned that they are passionate about music, going to a concert would be an ideal choice. 

While the location is important, it is what you do that matters most. You should plan at least two fun activities to do throughout the date. Let’s say, for instance, after seeing a movie, you can invite them for drinks at a nearby coffee shop or bar.

Planning at least two activities keeps things fun and gives the impression that you planned the date. Also, you should expect to pay for the date. Sure, the norm is for guys to pay for the date, but it shouldn’t always work that way. Regardless of your gender, it’s only fair for you to pay for the date if you’re the one who initiated the date.

Lastly, the first date should last between 3 to 5 hours, and not any longer than that. It is sufficient time for the two of you to enjoy each other’s company whilst leaving both of you wanting more, which is exactly what you should be aiming for on the first date. You want the other person to look forward to being with you again.

5 Steps to Ask Someone Out on a Date Over Chat line Conversation

1. Find the right timing.

Obviously, you don’t want to ask someone out when they’re having a bad day. You want to initiate a date in the middle of the conversation when you’re certain that they’re in a good mood. If you’re not talking at the moment and you want to make the move, you can simply ask if it’s a good time to talk. If they say yes, do it. Otherwise, ask when would be the best time to talk.

2. Have a unique approach.

If you want to land a date, saying “Will you go on a date with me?” isn’t going to cut it. Sure, it still sounds romantic, but it isn’t original. You have no idea how many people in the chat lines may have already asked them the same thing. You want to stand out among everyone who may be asking them out. Otherwise, you’re just one of them.

3. Be specific.

Being specific means letting them know what you have planned. Instead of asking “Can I take you out to dinner?“, you can say something like, “I have reserved a table for two in this newly-opened steakhouse and it would be amazing if you can come with me. I also bought two movie tickets so we can do something after dinner.” Most people would agree on a planned romantic date than a spontaneous one, especially if it’s the first date.

4. Ask for their opinion and give them an option.

After letting them know what you have planned, you can always ask for their opinion by simply asking, “What do you think?” By asking this, you’ll know whether your plan sounds good to them or they have a suggestion in mind.

Also, it is important to give them an option in regard to the date and time. You can say something like, “We can do it on Wednesday or Saturday evening. Let me know which works best for you.” Giving them an option lets them know that you are considerate and respectful of their time.

5. Respond casually.

When you reach this step, they have already probably responded with either yes or no to your invitation. If they agree to go on a date with you, don’t act too excited about it. If they said yes, you could simply respond, “Great! See you then.” If they say no, say, “It’s not a problem! Have a great day.“

When faced with rejection, it’s best to end the conversation right there because you might just be wasting your time. And unless they give you a reason that implies you can try asking them out again at a later time, it’s not your job to figure out why they said no and whether you can try again or not.

Do’s and Don’ts When Asking Someone Out on a Date

Asking someone out on a date can be nerve-racking. Here are some do’s and don’ts that you should bear in mind to keep you on the right track.

What to do when asking someone out on a date:

• Use their recorded greeting to your advantage. Listen to their recorded greeting again and see if there’s anything that might help you in planning a date. For instance, they mentioned their hobbies include sports, and you might want to consider inviting them to watch a baseball match together. This tip works only if they have recorded a pretty detailed greeting. Otherwise, this may not be helpful. In that case, pay attention to your conversation. They might be dropping subtle hints somewhere.
• Be a good talker or try to be one. Saying the overused “hey” and “how are you?” won’t get you anywhere near a date. These may work as a conversation starter, but it shouldn’t come up more than once. Sure, not everyone is born a naturally great talker, but everyone can try. If your exchange over chat line is dull and boring, you can’t expect the other person to go on an actual date with you to have the same tedious conversation.
• Be straightforward and make it clear that it’s a date. Beating around the bush does nothing but confuse the other person. Also, don’t attempt to pull out the “let’s hang out as friends” card, especially if you’re looking to make this date a potential relationship at some point in the future. When asking someone out on a date, it is best to express your thoughts straight to the point and make sure that the other person is aware that it is a date. Otherwise, it may cause complications down the road.
• Speak nonchalantly. The guaranteed way to get rejected when asking someone out on a date is to sound too overwhelmed. It’s science: we tend to stay away from people who like us too much and obsess over those who don’t want us. Now, this might sound like a bad thing, especially if you’re really into the person you’re talking to, but that doesn’t mean you can’t use it to your advantage. It’s okay to let them know that you like them, which is exactly why you’re asking them out, right? But it is also essential that they’re aware that your world doesn’t revolve around them. If they agree to go out with you, great. If not, you wouldn’t beat yourself up over it.

What not to do when asking someone out on a date:

• Don’t let them feel pressured to say YES. Saying, “I have already planned everything so I would be devastated if you turn me down,” is manipulative. But saying, “I have an exciting plan in mind, and it would be amazing if you can go with me,” is respectful and considerate. Ultimately, whether or not your invitation will make the other person feel pressured boils down to one thing: your choice of words.
• Don’t rush. Rushing into asking someone out on a date when you only started talking to them one day ago will most likely slap you with the dreaded “no”.When you’ve only been talking for a few days, you probably have not yet piqued their interest enough to go on an actual date with you.
• Don’t ask. There are a lot of ways you can ask someone out on a date without sounding like you’re asking. Instead of asking, you can say how much fun it would be if they would come with you. It could be something as simple as, “I bought two tickets for the movies showing this weekend, and it would be entertaining if you came with me.” Saying this will not only let them know that you have a specific date planned, but it also tells them that you want to enjoy it with them.
• Don’t respond negatively to rejection. Let’s face it: even the person who possesses all the excellent characteristics that most people are looking for may still get rejected for some reason. Understand that rejection isn’t personal. Most of the time, it has little to do with you and a lot more to do with themselves. Perhaps they aren’t ready to go out on a date yet, or they want to get to know you more. Rejection stings, but it’s not worth taking the low moral ground by getting angry or saying rude remarks when they said no. However, the good news is, if you adhere to the guidelines and tips in this article, you might not have to worry about handling rejection.