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18 Ideas for How to Ask for a Second Date with Success

18 Ideas for How to Ask for a Second Date with Success

To ask for a first date was one massive hurdle, and getting a second date can be just as challenging.

But we said challenging, not impossible. In this post, we will be focusing on what it takes to ask for a second date and, more importantly, we’ll look at some actual examples of how to ask for a second date.

Let’s get started!


How to Ask for a Second Date: Things to Consider

If you want a good chance of getting a “yes”, there are some things you must know and consider. The main ones are:

01How the first date went
If you had a good first date, then your chances of hearing “yes” when it comes to the second are much higher, and you probably won’t have to jump through too many hoops.
However, if your first date didn’t go so well, your chances decrease significantly. You will have to ask yourself why it didn’t go well. Was it your fault? Did you show up late and make him/her wait? Did you make him/her feel uncomfortable? Were you talking more than listening? Was it something that was out of your control? For example, did it start to rain? Was the food late?
If it was your fault, you will have to persuade him/her to go out with you again by apologizing or proving to him/her that a second date will go better. If it was not your fault, you have better chances.


01 woman hugging a man inside the train
Photo by Jonathan Borba on unsplash


02Did they seem into you after the first date?
After a good first date, people tend to feel more comfortable around each other and will speak more freely. You may even have longer, flirtier conversations. But if the date didn’t go so well, or if that person just isn’t into you, the conversations you have will be bland or even non-existent. If that’s the case, a second date is not likely to happen.


02 couple in front of white pinstrip

Photo by Hian Oliveira on unpslash


Timing is very important, and it depends on several factors, the main one being the other person’s schedule. If your date attends school or works, it is highly unlikely that they will have time to go on a spontaneous second date with no notice.
Also, if your date has something big coming up, like exams or a presentation, don’t ask for a second date right away. Give him/her some time before you plan another date.
If you want to hear a “yes”, from your date, it is best to give them about a week’s notice and make sure that the date is on a weekend to improve your chances.
If your date has something big coming up, like exams or a presentation, don’t ask for a second date right away. Give him/her some time before you plan another date.


03 white ceramic mug with coffee

Photo by Estée Janssens on unsplash


Rejection is always a possibility, but that does not mean the second date will never happen (unless they explicitly say so). If rejected, how you react will send a message, and you want it to be a positive one.
Do not beg or act overly desperate because you will come off as weird. Don’t get angry because this will turn off the person completely. Instead, accept your rejection with grace and leave the offer open. They might just be too busy at the time you asked.


04 a woman who refuses

Photo by acworks on photo-ac

Note that every situation is different, so you will have to apply these guidelines to your individual situation.


Ideas for How to Ask for a Second Chance When the First Date Was Great

Like we said earlier, it is much easier to get a second one when the first date went well. Here are 7 great ideas for how to ask for it.

01“Last night’s karaoke was so much fun! We should definitely do it again next week.”
It doesn’t have to be karaoke for this to work. It can be any weekly event at a club, bar, restaurant or wherever that you had your first date. It’s only important that you both enjoyed it. Your date will say “yes” if they had a good time.


01 man singing in karaoke

Photo by James Dominko on unsplash


02“I hear that skating rink you were talking about is open on Sundays.”
Ever heard of suggestive psychology? Well, this is one example that will surely get you a second chance. When the venue was their idea, you’ll have an easier time getting them to agree to go.


02 city building cityscape

Photo by Yomex Owo on unsplash


03“I have to meet up with a client at 2:30 today, but I have an hour to spare. Do you want to grab a quick bite?”
This is a great line to use. It won’t make you seem desperate or too available. Using the word “quick” is likely to get you a second date, especially if they aren’t sure about how they feel about you.



04“I’d love to hear more about [insert interesting story that got cut off]. Do you want to finish telling me over lunch tomorrow?”
If you were on a date and it got cut short in the middle of a story your crush was telling you or something that they were explaining, you can use this to meet him/her the next time.
Because the date is for a specific purpose and it’s at lunchtime (It’s unlikely that it will affect your date’s schedule much) you’ll have a good chance of winning the appointment.


05“You work too much. Cocktails this Friday. On me.”
This is more of a statement than a question, and it will work when they have been complaining about school or work. Offering them some peace is sure to guarantee a “yes”.


05 woman sitting while drinking wine
Photo by Louis Hansel @shotsoflouis on unsplash


06“Let’s meet up again Friday or Sunday for some ice-cream.”
When you use this, it should flow within the context of conversation, meaning you should have been talking about ice-cream, or another food item. It is likely to work since you aren’t giving the option of yes or no, but of Friday or Sunday.


07“Hey, do you know this place? *send him/her a picture and wait on his/her response* I’m planning on checking it out. You should come.”
If your date does not know what the place is, take the time to explain the venue before you invite them to join you.
This strategy gives them something to look forward to—if they’re interested.


07 date near body of water

Photo by Matt Mariannelli on unsplash


08“I’d like to see you again. Does Friday at 7 work for you?”
This approach works when you are positive they are into you. The key to this message’s success is that you are catering to their schedule and not necessarily to yours.


09“I want to see you in something other than your work clothes. Do you want to dress up and go out this Saturday?”
This can work in person or over text with someone you see daily who is clearly into you and had a great time on the first date.


Ideas for How to Ask for Another Chance When the First Date Wasn’t Great

So your first date didn’t go well, but you are still interested and want to give it another shot. Here are 9 ideas that will make that second chance possible:

10“Hey, I know that last date sucked, but if you’re willing to give us another chance, I’d love to make it up to you on Saturday.”
This is likely to work because you are being honest about what happened. They will appreciate the sincerity.


11“How about next time we do an indoor activity? My mom’s stewed beef recipe is a charmer.”
If you are discussing how the first date went, this is a good way to sneak in the idea of a second date. If they say yes, you can go ahead and propose a day and time for the second date.


man and woman cooking

Photo by Edgar Castrejon on unsplash


12“It’s obvious that neither of us had a great time last night, but we have chemistry. What would you say to a do-over?”
This is good to use when it is obvious that your date likes you, but your first date did not go well.


13“Nobody’s perfect, and being around you made me super nervous. I’m sorry I blabbed away all night and didn’t give you a chance to speak. If you give me a second chance, I’m all ears.”
It is good to take responsibility for what you did during the date. Your crush will respect this and may even give you a second chance.



14“I want to talk about what happened on Wednesday. Would you meet me at 8 in the lobby?”
If you live in the same dorm or in the same apartment building as your crush, you can use this as a way to make up for a bad date.
Since you live so close together, it won’t be a big deal for them to come downstairs. And when they do, use that time to make up for the last date by having a seat somewhere and offering to buy him/her a drink, thus turning it into a second date. It’s sneaky, but it might work.


vacant room interior design
Photo by Michael Glass on unsplash


15“If I had a time machine, I’d go back in time and make our first date a whole lot better. But since I don’t, can you please do me a favor and forget it even happened?”
This makes light of what happened. Just be careful though, because it will not work for every situation and it depends on how bad the date was.


black and white photo of clocks

Photo by Andrey Grushnikov under pexels license


16“Roses are red, violets are blue, what I want more than anything is a second date with you.”
Okay, this one is very cheesy, but it can make them laugh. Laughter might help to change their mind about going out again with you.


17“I’m sorry for [insert what you did wrong]. If you want to try again, I’d be happy to take you on a make-up date.”
The best types of apologies include showing you know what you did wrong. This approach is likely to work because you have done that in a sincere manner.


18“I’ve had a lot of time to think about why our first date went wrong, and I’m pretty sure I can make things right. What do you say?”
Your date will (hopefully) appreciate your thoughtfulness and effort to right any wrongs. Your confidence will also help to persuade them to say yes to another round.



Now that you know what to consider when asking for a second date and have real-life examples, it is time to put what you learned into practice. You can thank us later. Good luck!