hey (girl’s name), you recovered from your crushing defeat yet 😉 We could find out but I was thinking drinks for our next date What’s your schedule look like this week? Let’s do 7:24 then Awesome, 7:24 at (name of venue) then Hey (her name), you picked a cute outfit for our date? 😉 Need help choosing or you gonna surprise me? Keeping the mystery alive 😏
They have been on their first date. They went bowling and he beat her in the game. The coach advised he reopen the following day using callback humor relating to the date as this is often the best way to reopen, spark conversation and lead to a second date. Even though they have met in person and you don’t have to put as much work into the lead as before the first date, the student had to keep the lead warm until date number two. This is where the “you picked a cute outfit for our date yet? 😉” works well to reopen the day of the date to check in with her.
 This message works as it connects you two in a shared experience. It is also good because it is teasing her about her loss without being too harsh or rude.
hey (girl’s name), you recovered from your crushing defeat yet 😉
assistant
 I’ve recovered from losing, but throwing the ball behind me… still recovering from that one 😂
Her
 They say three times is the charm for a reason, the odds are on your side…
Student
 Are you saying the next time I play, I’m going to win???
Her
 This message works here as, to keep things interesting, it’s usually best to vary the type of dates you take a girl on. It would have been a little weird if they had gone bowling again. 
We could find out but I was thinking drinks for our next date
assistant
 As much as I enjoyed losing to you in bowling, drinks would be a good second date 😉
Her
 The first date went very well so there is no need to do lots of talking/ courting between the first and second date. 
What’s your schedule look like this week?
assistant
 Depending on my work schedule, I generally am free most weekdays after 6:30
Her
 What about you?
Her
 I could work with Tuesday around 8pm, how’s that?
Student
 You wanna do 8pm again? Haha
Her
 You got a point, we would be missing the end of happy hour
Student
 Right haha so maybe a little earlier
Her
 This message is so specific when arranging the time to be a lighthearted tease. 
Let’s do 7:24 then
assistant
 Very particular, but works for me 😂
Her
 This message establishes the overall plan for the date.
Awesome, 7:24 at (name of venue) then
assistant
 See you then haha
Her
 You don’t want to set up the date, even a second date, and then not talk the the girl at all before you meet. You need to keep the lead warm. A good way to do this is ask if she picked a cute outfit for their date. 
Hey (her name), you picked a cute outfit for our date? 😉
assistant
 I definitely have a couple of options ☺️
Her
 This message creates the idea that she wants/ is trying to impress him by what she wears. 
Need help choosing or you gonna surprise me?
assistant
 I think I’m gonna go with surprise
Her
 This message creates a flirty tone like she is hiding something explicit from him. It also creates the role play of them being a long married couple who are trying to keep the mystery alive.
Keeping the mystery alive 😏
assistant
 Oh definitely 😉
Her
 I’ll be there in twenty to get a table, lmk when you arrive.
Student
 Okay! I got off work a little late so I might be a couple minutes behind, but I’m on my way
Her