“Just send it and immediately delete it so I can never read it!”

Fingers flying in a text..,

“Okay sent and deleted. Let’s go drive around!”

Yes that’s an actual conversation between my daughter and I. I had her text Brent to ask him one very specific question…

You may wonder a couple things… How did I get here? Why did I have my teenage daughter send a message? And finally, what did Brent say?

How did I get here?

So Brent and I had some really great conversations after the best moment of the dinosaur conversation. Honestly, I was looking forward to our talks and to see him. It was becoming a “thing” and a regular thought for me. I’m not the best in the friend zone.

As you guys may remember, I have wrote about the friend zone before. The hurt feelings and confusion I had then.

I am not a serial dater (when I’m really into someone). What can I say I’m monogamous from actually liking someone to the end?! When Brent caught my eye I was smiling from the inside. A little too natural and easy… I was in the monogamous liking zone.

Now, you can argue that the friend zone ended really good before. You’d be right, for sure, but I am not in a place to risk it. You guys know I have been pretty badly hurt before and learned to not take too many risks when it comes to my heart.

Plus this time with Brent it was different. I could tell. Jack always struggled with us being friends and Brent it was really black and white. There has never been a question of intent. I found myself replaying our conversations to see if there were any hints he may interested in anything down the road. I could only find a weak few.

I got scared of the place I was in. There was a lack of clarity, unknown amount of time it could go on and some drama that came with it. Brent does a great job of connecting with all people and making them feel special, so it wasn’t surprising I wasn’t the only one interested. I don’t compete so it makes me feel and act really awkward. None of these things are in my comfort zone so I needed to move on.

Plus the final moment was when I talked with my girlfriend. She listened to how amazing I think Brent is and then she said, “Jill you also so ducking (yes I am not changing that spelling 🦆) amazing! You shouldn’t settle for less than a man who is fully into you.”

So it was that point that I decided that it wasn’t fair to just stop being friends with Brent. I needed clarity.

Why did I have my teenage daughter send the message?

So I tried and tried to summon up the courage to ask. Nothing sounded right when I texted. It sounded cheesy and stupid. After all this had been the first guy that truly made me think “Jack who?”

This text was going to change things. It was going to really take the elephant out of the living room. My perception and feelings about our friendship were going to shift. It needed to be asked so I can move on.

So one of my guy friends gave me this advice…

My friend was right it didn’t matter how I asked Brent he either was or wasn’t interested. So after a few more texts and deletes I handed the phone to my daughter.

I told her my purpose and she started moving her fingers and clicked send. I instantly felt relieved.

I asked her to delete it as I didn’t want to second guess how she asked. I had done that too much, plus, it wasn’t going to change the answer. It was sent and deleted and my daughter and I took a 20 minute drive. I needed the loud music, dancing and distraction.

What did Brent say?

I got back and saw his reply (something like this I deleted the actual message… I have this weird habit of deleting messages that make me feel awkward)..

I see you as a friend ☺️

I was actually first okay with that reply. I even smiled (see why I can’t be friends?!). I had this idea that he would send a long text about how clingy I was to ask such a question. So the clarity was reassuring.

Afterwards I was a little bummed. It was great having a guy that actually thought about relationships in some ways the exact way I did. Just openness, clarity and teamwork.

So Now What?

I told Brent I needed a friend break. I needed to move on past the feelings. He was actually understanding and kind about it. It was once again a very grown up reply.

It is early on but I’m grateful for what I’ve figured out so far from Brent:

• I can move on past Jack and really be into a guy with no reservations. Jack texted me during my “Brent daily texting friend time” and of course I was happy but not WOO HOO! That’s a win!

• I need a man that will care enough to challenge my thinking. Brent and I had many debates and discussions. While I didn’t always agree I always knew his intentions were pure.

• I want a man that will also challenge himself and his thinking. One that will listen to understand what I’m saying and chat about relevant topics.

• Finally, no matter how perfect or “in a box” someone seems, there are many dimensions to everyone. I should never assume anything about anyone.

As for the future of our friendship, I am not sure. I would love to say we will once again be actual friends. I feel like he is such a wonderful guy and would be a great keeper of a friend. I just don’t know realistically if that will happen. The truth is I don’t know and will just focus on staying in the now and what I need to do today.