Fun Riddles Over Text

by Bobby Rio


Since so many people enjoyed Race’s last article providing some ways to re-engage a girl who has stopped answering your texts. I asked him to write another article for my readers.

btw- Race has some more really solid texting advice here.

How to Use Fun Riddles to Kick Start New Conversation

By Race DePreist

guy making girl laughHave you ever had the experience where you had a great text interaction with a girl and then you run out of things to say? Or perhaps it has been a day or two since your last interaction. It ended well but you are stuck on how to start it up again without sounding needy or overbearing.

This used to happen to me all the time. Then one day a friend I hadn’t talked to in a while sent me a riddle. Without thinking this odd or random that he would text me out of the blue, a strange thing happened. My brain immediately went to work trying to figure out the answer. It totally distracted me from what I might have normally thought or felt getting a text from someone I hadn’t heard from in a while.

Now even if it hasn’t been a while since you talked to a certain girl, this still works wonders. It is a fun way to effortlessly slip into a new conversation thread with a girl. Her mind will immediately be pre-occupied with figuring out (or if she is lazy, finding out) the answer to the riddle.

You have grabbed her attention completely. After all, our brains are wired to immediately search for answers as soon as we ask it questions.

Let’s check out 2 of my favorite’s that I use all the time.

Q: What has a bottom at the top?
A: Your legs 🙂

Q: What is brown and sticky?
A: a stick 🙂

The best part is that when you use one of these silly riddles, not only will you be starting a new conversation effortlessly but she will already be in a good mood because the answer is funny.

Here I’ll show you these two riddle in action.

In Action:

3 Questions that Turn Her OnRace: what’s brown and sticky? 3:03 PM
Marisa: Umm? 4:44 PM
Race: a stick 🙂 4:46 PM
Marisa: Ur a dork:) 5:16 PM
Race: haha so you have noticed 5:17 PM
Marisa: But i like it;) 6:30 PM
Race: i am excited for sunday 🙂 7:18 PM
Marisa: Me too me too:) 9:46 PM
Marisa: Wher r u? U should come hangout! 2:14 AM
Race: Where? 2:46 AM
Marisa: XS 2:50 AM
Race: Ooh la vanity. How is it? 2:53 AM
Marisa: Fun.. U should come thru…i wanna see u! 2:54 AM
Marisa: ?? 3:32 AM
Marisa: Ummm? 4:06 AM

(I think she really wanted to hang out but I fell asleep..oops)

In Action:

Race: what has a bottom at the top? -Race 10:49 AM
Lauren: hmmmm…? 10:50 AM
Race: your legs of course 😉 10:52 AM
Lauren: lol…clever 10:54 AM
Race: i think it was one of my nephews favorite jokes a while back lol 11:00 AM
Lauren: I like those corny jokes ; ) Heres one for you…How do you wake up Lady Gaga? 1:08 PM
Race: haha poke her face I am assuming…that was a facebook update phenomenon a while back 1:09 PM
Lauren: oh it was…lol…my students told me that…What did the little mountain say to the big mt? 1:10 PM
Race: Ooh you got me on that one 1:12 PM
Lauren: “Hi Cliff!” 1:12 PM
Race: Haha nice one 1:53 PM

Often times girls will throw a riddle back at you. This is a great way to learn new ones that you can use in the future. One time I went 2 hrs with a girl sending new riddles back and forth. Not only was it fun but I got a lot of brain exercise in that day.

Another funny side affect of using riddles to start up new conversations is sometimes you will get back some pretty funny replies from clever girls. Check out this one I got just yesterday.

Race: what has a bottom at the top? 11:59 AM
Sara: A gayman 12:00 PM
Race: haha clever…I was going to say your legs 12:00 PM
Sara: My punchlines better 🙂 12:01 PM
Race: do you want a cookie or perhaps a gold star? 12:12 PM
Sara: Gold star gold star!!! 12:19 PM

Pretty funny huh?

There are thousands of silly riddles like this. Just google “silly riddles” and find some. You want them to be a one liner and have a funny answer.

After the riddle you can simply transition into a normal conversation using the tips and techniques in Text That Girl.

Q: Who is getting out their phone right now to send a riddle to a girl?

Ok so that wasn’t actually a riddle but you get the idea. Have fun with this one.

And if you like this structure, check out more of my examples and structures for texting here.



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