Skip to content

What’s the Ideal Time Between a First and Second Date?

What’s the Ideal Time Between a First and Second Date?

What’s the Ideal Time Between a First and Second Date?

Timing has always been a big part of dating.

In Hollywood its significance has played out in various famous scenes, perhaps none moreso than in Swingers when Jon Favreau’s character is literally checking off the days in his calendar, waiting until there are three red Xs in a row before phoning his new crush. 

Figuring out the ideal time to contact a woman after receiving her number is a puzzle that men have yet to piece together. Likewise, men have also been flummoxed by the ideal time to wait between a first and second date.  



There is no three-day rule like Vince Vaughn proposed in Swingers. The duration of time you should wait until a second date is dependent on a number of variables. 

Schedule a date too early and the tension isn’t given enough time to build, schedule it too late and the flame that you kindled on your first date has all but fizzled out. Together we’ll explore the ideal waiting time between a first and second date.

Ideal Time Between the First and Second Date: Various Scenarios

Best Day of the Week for a First Date

When the second date is scheduled largely depends on when the first one took place. 

The best day for a first date is Saturday afternoon when it’s still light out. 

If you’re already a MegaDater you’d know that first dates should last no longer than an hour with no more than $10 being spent. Saturday afternoon as opposed to a weeknight enables you to easily adhere to these dating guidelines.

Asking a woman out right after work will likely lead to dinner or drinks in a boisterous and crowded bar awash in 9-5ers celebrating the end of the workday. These aren’t ideal conditions for a first date. 

First dates should also be daytime dates. Any date taking place at night takes on a romantic vibe. It’s also at night when women generally feel more vulnerable.

Your objective on a first date is to make her feel comfortable and safe by creating a receptive and warm environment. A stroll and ice cream along the boardwalk on a Saturday afternoon illustrates a safe space. Shouting over fellow drunkards to get your point across in a rowdy bar does not. 

If Saturday afternoon is out of the question, try Wednesday right after work.

Just make sure that it’s light outside when the date begins and ends and that you’ve made it clear that you won’t be spending more than an hour with each other.

Try not to spring this on her if possible. Instead, plant the idea prior to the date that you can only interact for one hour. I train my clients to spend no more than $10 and one hour on a first date because you’re essentially dating a stranger. Why would you promise to invest a copious amount of time and money into hanging out with a stranger?

If Your First Date Was on a Saturday

The armchair Don Juans might advise you to see her a few days after the first date, no matter when the date took place. In short, they’re wrong. 



If the first date occurred on a Saturday, the second should also take place on a Saturday. Allow me to elaborate. 

Midweek dates are difficult to pull off because of work or school commitments. If they do happen generally they’re looked down upon. The thought being that nothing really meaningful can take place midweek. We live for the weekends, not a Tuesday night date with someone you met on an app. Apart from the ease of scheduling a date for a weekend, there’s another reason for doing so.

Each date should get progressively more romantic. Perhaps there was little touching at all on the first date, that’s fine – it’s a first date. However, the second date has its own set of rules. 

Second dates should both be physical and free. Physical because it’s easier to touch each other and form a bond if you two are moving around. Free because free dates weed out both gold diggers and women that aren’t that interested in you.

It’s quite difficult to schedule a hike, bike red, swim, or workout midweek. That’s why second dates are best saved for the weekend. 

A first date on a Saturday followed by a second on the upcoming Saturday means that there’s a seven day waiting period. I know that seven days seems like quite a while and that you may have the urge to text her midweek – don’t.

Carrying out an in-depth text convo midweek will deflate any tension you built and give you little material to talk about on Saturday. Wait until the day prior to text her just to confirm that you’re still on for Saturday and the express your excitement. 

Should you two are both off work midweek, then go ahead and schedule a midweek date that ideally takes place on Wednesday. 

If Your First Date Was a Wednesday Evening

If you crushed that first date you had on Wednesday, awesome, but don’t let that momentum you’ve built hit the doldrums. 

At the end of your first date -regardless of when it took place- use a TDL to ask her on a second. TDL stands for time, date, location. It’s what you should use every time you ask her out.



An example of a TDL you might use at the end of a first date would be, “So you’re awesome and we should definitely see each other again. Want to go for a bike ride through the Headlands this Saturday at say, 1 p.m.?” 

A TDL works because it defines the date in full. Most men ask women on nebulous dates by proposing, “hey, wanna hang out sometime?” That’s a nothing request. This on the other hand gives her a concrete engagement that she can either reject, accept, or amend. 

A TDL should be used at the close of a first date. She may have been asking herself why the first date only lasted an hour. Rightly so, she may wonder if you like her or not. Quash these fears by using a TDL to ask her on a second date. 

Should you two have gone out on Wednesday, set up a second date for Saturday afternoon, just three days away. 

If Your First Date Was on Any Other Day

Chances are that if your first date took place on any other day, it was a weekday. If this is the case shoot for a weekend date. Again, chances are higher that she’ll accept a weekend date opposed to a midweek date.

No matter how awesome you think your TDL is, it will inevitably be rejected. Whether there’s no connection or she’s busy is something you’ll have to figure out. Do so by proposing multiple TDLs. Should she say she can’t make it Saturday ask her to a Sunday date, “No worries, how does Sunday at 2 at the Botanical Gardens sound?” 

Whether or not you ask her out again depends on her response. If she doesn’t offer to reschedule or apologize profusely, then she’s probably not into you. Even if you sense this, give her the benefit of the doubt and propose yet another TDL.

If she rejects you three times without suggesting a new time or activity don’t bother trying to coax her into a second date, and instead save your energy for women that are actually into you. 

It can be awkward getting your TDLs continually rejected in person. If she already said no to two TDLs asked in person, keep that third request tucked away. Wait a day until you ask her out on an original date.

Let’s say she’s turned down numerous date ideas. As a last-ditch effort write to her saying, “No worries Stacy. Seeing as how I don’t feel like getting rejected again, let’s swap gender roles so now the onus is on you to ask me out. You know I’m into you, now the ball is in your court.”

You Should Never Be Asking Yourself the Ideal Time Between a First and Second Date

The attraction you built on your one-hour first date can quickly fade. To indicate your interest and secure a second date you’ll need to use a TDL at the end of your first date while the feelings are still running high. 



When you ask her on a second date at the end of a first you’re ensuring that you’ll see her again. You won’t have to play the game of purposefully waiting a couple of days to contact her again. Asking her on a second date then and there erases all the callow mind games from the equation. 

A second date is just the beginning of your fledgling relationship. To ensure that everything goes smoothly schedule a 1-on-1 Zoom session with me, your new professional wingwoman. I’ll walk you through what a successful second and third date look like. Should this relationship go sour, I offer plenty of coaching and matchmaking services that are sure to help you reach your dating goals this year!

Comments are closed for this article!

Featured Articles