16 of the Most Awkward Text Message Conversations Ever Sent

I came, I saw, I made it awkward.

Edmund

• Published in Funny
• December 29, 2018

Everyone has those great conversations where you just instantly connect with someone and it feels like you have known them for many years. On the flip side of that though you sometimes have conversations where at various points you just don't mesh.

It may be that there is a miscommunication or you might just be different people looking for different things out of the relationship... and then there are those with absolutely no filter.

Here are some hilariously awkward examples of these conversations from people who for one reason or another really did not interact well with one another.

Worst game of 21 questions ever.

Not everyone takes rejection well.

The only response acceptable for such a request.

A date so bad he had the guts to ask for a refund.

I mean sure that's one way to get people to talk to you but it's not recommended.

Weirdest request ever.

Wrong person bro.

Definitely not how you get a girl's number

*Questions what I actually just read*

Weird joke

The worst case of jealousy anyone could have.

I feel uncomfortable just reading this.

Why Steve?

Edmund