Sleeping with Friends

As the title suggests, I did something five weeks ago. And then again two weeks later. It should be mentioned that the first occurrence was at my mother’s wedding. I wish you read that wrong, but I am afraid you did not. I brought Dylan* as my plus one, knowing that I did not want a rando to escort me to such a meaningful day. Additionally, he has known the family for years and was best friends with my older sister before we became good friends. 

We were discussing it the other day, and we decided that we haven’t gone a day since 2017 without some form of communication. Within the past four years, Dylan and I both have had our fair share of hookups and each had a serious relationship too. Being that we talk most all day every day, we each knew an unhealthy amount each other’s love lives. 

The adage is that sleeping with your friends will ruin that friendship, because at thart point, you are no longer friends. I initially agreed with that, until I became one of the deniers. Nothing has changed since we’ve slept together… or had it??

Frankly, I do not know if I like Andrew like *that*. Prior to sleeping together, I would have said absolutely not but ahhhhhh maybe we would be good together?? He has been alluding to a lot of things lately

Pros/Cons of him:


  • Already good friends and know everything about eachtoher 
  • Potential for good sex
  • Ambitious 
  • Good looking 
  • Successful and on track to make $$$
  • Comes from similar background to me (ABQ)
  • Already in with the fam 
  • Likes to have fun and has a lot of friends 
  • Pickleball
  • Knows me very very well. What triggers me, what excites me, what i like and dont like 


  • What is he going to do with his life once excessively binge drinking 2x a week is done 
  • Doesnt have many interests 
  • I feel like i shouldnt like him
  • Lives in austin lmao 

I am following up on this story, 6 months later since I must have gotten distracted. Probably by a call from Dylan, rehashing his weekend of clowning as he does most weekends. Since our last hookup, I have seen Dylan multiple times, but no hookup has ensued. Have there been opportunities? Yes. However, drunk me has made it clear it is not a good idea and Dylan thankfully respects my boundaries. In my next blog post, I am going to write about a dating experience where I realized I was not attracted to a guy’s demeanor – despite the fact he embodies many traits I want in a partner. 

BTW- May or may not have booked a trip to his city in a month. Granted there are other reasons I am going but STILL. More juice to come. 

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