When And How To Ask Your Ex Out On Second Date Or Third?

when-should-i-ask-my-ex-for-another-dateSo you made it through the first date with your ex, when is the best time to ask your ex out on another date?

Here are some of the key things to remember as you transition from a first date to a second date to getting back together. These are not “rules” but general guidelines. If your instincts are good and have worked well for you in the past; then trust your instincts over any “rules” when dealing with other human beings.

1. Try not to ask your ex for a second date right away

If the first date went great, both of you will spend the next day or two analyzing every word and every gesture to convince yourselves that it really was as good as it was.

You have a better chance of getting a second date if your ex has had enough time to process how they feel. It doesn’t mean you don’t contact them, just that you don’t ask for another date immediately. The time between the first and second date should be 2 – 4 weeks. If the second date goes well, the third date can be as soon as 3 days to 1 week.

2. Build more momentum before asking for another date

The tone of communication after the first date will tell you if your chances of getting a second date are good. Build on that positive energy to create momentum.

Since you are the one still doing most of the “work”, you most likely will be the one to ask for a second date. Keep it short and sweet, preferably suggest “I’d like to see you again,” rather than ask “what are you doing Friday?”.

3. Make no assumptions

Many men and women after one great date make the mistake of assuming that because things went well, it’s smooth sailing from here onwards. Wrong. Even after several dates, your ex can still turn around and stay they want to go slow, they don’t think you should be seeing each other anymore or they don’t want any more contact with you. So tread very carefully.

4. Make sure your intentions are clear

By the second date, it should be clear to your ex that you want them back. If not, you may end up “hanging out” as friends for the next several “dates” or you may end up becoming the second choice when the first choice is unavailable. If you have been following the advice in Dating Your Ex, this should not be a problem for you. All the steps up to this stage pretty much make your intentions clear.

 5. Be confident and assertive but not pushy

Don’t be wish-washy about what it is you’re asking your ex for. You’re more likely to get a positive response if you’re confident and assertive but not pushy. You’re also likely to get a positive response if you have a clear plan.

Something along the lines, “I would like to see you again. Let’s get together this weekend if you’re free. Remember the X band, they’re’ playing at Y this weekend from 5 – 8 pm. Afterwards we can grab dinner at Z. I think it’d be fun. What do you think?”.

6. Don’t be too attached to the outcome

It’s okay to ask someone out on a date and even want them to ‘yes.’ But don’t be too attached to the outcome that you need them to say, ‘yes’.

If your ex turns you down for a second date but is still open to communicating that’s okay. The door is still open, things could be different next week or the week after. Just make sure you keep building emotional momentum. You need that wind under your wings to carry you to the next level.

If you are struggling with building emotional momentum, I am happy to work with you one-on-one to develop a strategy/plan of action that’ll move things forward.


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  1. AvatarAvatarAvatarsays: Nick

    Hi I’d love to ask questions about working towards getting back with my ex. We’ve already had our first date

  2. AvatarAvatarAvatarsays: Brian

    Hi Yangki, thanks for this article and awesome blog. I just wanted to clarify, because your book lists several criteria for expressing that you still have feelings, one of which being “your ex is emotionally opening up,” and that timing is important. Here, you say you should do it by the second date. I’m just wondering if the second date is ever too soon.

    1. Yangki AkitengYangki Akitengsays: Yangki Akiteng

      The article does not say you should express that you still have feelings for your ex by the second date. It clearly says “By the second date, it should be clear to your ex that you want him/her back”. Very different from “expressing that you still have feelings” on a second date.

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