16 of the Most Awkward Text Message Conversations Ever Sent

I came, I saw, I made it awkward.

Edmund
  • Published in Funny
16 of the Most Awkward Text Message Conversations Ever Sent

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.

Worst game of 21 questions ever.

Not everyone takes rejection well.

Not everyone takes rejection well.Source

The only response acceptable for such a request.

The only response acceptable for such a request.Source
Source

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

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

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

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

Weirdest request ever.

Weirdest request ever.Source

Wrong person bro.

Wrong person bro.Source

Definitely not how you get a girl's number

Definitely not how you get a girl's numberSource

*Questions what I actually just read*

*Questions what I actually just read*Source

Weird joke

Weird jokeSource
Source

The worst case of jealousy anyone could have.

The worst case of jealousy anyone could have. Source

I feel uncomfortable just reading this.

I feel uncomfortable just reading this.Source
Source

Why Steve?

Why Steve?Source
Edmund