Now to learn to swim…

So I have an update for my last blog. Bear with me ladies and gents this will definitely be worth the read ūüėČ

So Jack*, yes the guy from way back in my blog Do you Know Jack? , and I finally had THE conversation.

Let me first clarify something because I was asked about this. ¬†Jack has never read my blog… Well once when we first started talking for about half a blog… then he stopped. But that was it. He has always said he would rather have the conversation than read about it. So, writing my blog before was really for advice and boy did you guys deliver!

So back to the conversation. We all know that I was drowning with what to do being lost in the friend zone. So I prepared a speech… a well thought out speech… a speech I ran by my closest friends… counselor… grocery store clerks… clergy men of other denominations.. you know everyone. ¬†I wanted to make sure I was sending the right message, was vulnerable and saying exactly what I meant.¬†I didn’t want to blow it because I’ve liked this guy forever.

So one Wednesday we’re texting ( like we do everyday) and he says he’s having a rough day. He was going to work out and then stop by and get a drink. So I gathered up enough courage and said “Well if you’re looking for a drinking buddy my hair and make up is looking hot!” I NEVER do that kind of assertive thing but I’m working on putting myself out there so I texted it. I then turned the phone over and walked away. I didn’t want to watch¬†my phone for the answer … I needed the breather after the whistle notification.

So he replies… I breathe…and read¬†“How about 8?” WOO HOO!!!

My actual look that night..

So now we have an unexpected hang out and I was pumped! I told myself I wasn’t going to have “the conversation” since he was having a rough night but would enjoy the night out with the hottest guy in my eyes!

We get to the bar and find out it’s Karaoke Night!! What! What! My favorite! We have a random guy come sit with us who explains how seriously he takes karaoke and Jack asks him all about his practice habits. I’m impressed because it shows me how Jack¬†can go along with pretty much any conversation. His improv skills are off the chart. So Jack and I make the best of the night! We drink (a lot) and sing along with all the best karaoke songs! Can you say Miley Cyrus “Party in the USA”? Yes we sang along!

As the drinks are flowing we start being friendlier and friendlier. Not inappropriate for public friendly…just flirty. It’s cute and of course I like him so I’m into it. So after several drinks we decide to head out.

We’re walking to the car arm in arm and this is the moment..

I decide NOW… IS THE TIME… for THE conversation…

(Paraphrased conversation hitting the key points and I’m sure removing out a lot of hand waving, repeating myself and I believe dropped keys… twice)

What I WANTED to say: So Jack, I have really wanted to talk with you about something.

What I ACTUALLY¬†said: So you want to hear the speech I’ve been practicing for weeks or do you want me to wait until the next time we chat? No seriously.. I’ve been practicing for weeks…for weeks.

HIM:¬†Weeks? You’ve been practicing for weeks.. Yeah lets hear this..

What I WANTED¬†to say: You know how I feel about you. I think you are one of the funniest people I know and I have a blast when we hang out. I love how good of a dad you are and how you remember all the little quirks about me. You make my day better when I talk with you and I know that I’ll be a better person having known you.¬†

What I ACTUALLY¬†said: You know you’re great… like great… and wonderful (with giant hand motions)… like awesome. Did I say great? Funny!

HIM: Thanks Jill! You’re great too.¬†


What I WANTED to say: I have had a lot of fun with this dynamic we have but I wanted to let you know my experience during our time. 

What I ACTUALLY¬†said: Yeah so let me tell you about me and the time we’ve been talking.¬†

HIM: Jill! You better not be ending this…¬†

There was no “what I wanted¬†to say” for him to interrupt me. I should’ve thought of ground rules but golly geez no one interrupts Oprah when she’s giving a speech… so wasn’t on my radar. A total wing!

ME:¬†No no… it’s not your time to talk. This is my speech pay attention.¬†I’m not at the end and I’m not ending it. I’ll let you know when it’s your time to talk.¬†


What I WANTED¬†to say: So during our time I haven’t really been able to give other guys a chance. ¬†I have gone on several dates and even a couple dates with a couple of the guys and each one of them is in the friends zone before they even walk into the door. I even had a guy ask me to be his girlfriend and I turned him down. I have found that no one can compare to the connection we have. (Pretty much what was in my blog)

What I ACTUALLY¬†said: So you know I go on dates right. Well two guys on Monday (yes true story) and I just don’t like any of them. ¬†I go on dates and nice guys. Like really nice guys but no chance for them. None of them. They just don’t compare. No one compares.

HIM: Whoa.. that’s a lot of pressure.

What I ACTUALLY¬†said (which mirrors what I wanted to say): No it’s really not. I didn’t tell you this because I wanted something from you. I am telling you this because I need you to understand my experience in this whole thing. That I’m not a cool girl. I’m not the girl that can really like one guy and then date other guys. I’m just not like that. I’m trying to be like that so we can stay friends but I’m just not. I’m just not cool.

HIM: That’s one of the things I like about you, that you’re not the cool girl.

Now I’m off the rails…. legit making it up as I go. That’s where I thought the conversation would end. Luckily for me it didn’t

ME: Then you go and get into an open relationship! What the f*&$k was that about? I mean really?!

HIM: Yeah I’m not… that ended a couple weeks ago.

Because like you Jill…

I’ve found out that no one can compare to you.

I always think ‘Can I talk to her like I talk to Jill?’ and the answer is always no. So you know what… we should do this. Like really do it. Let’s figure this out Jill.


My heart was racing at this point… but I played it cool and stopped talking. I mean after all what was I going to say?!

Then he read my mind:

 HIM: Why did it take me so long? 

ME: I don’t know. I’ve known it since day one. You’re just a little slow I guess.¬†

So it’s official. I’m officially dating someone that I am just over the moon about. I never thought¬†that being friends first would actually pan out. The first time Jack and I talked I was timelines and demands. The second time (about 3 weeks later) I let it play out. I didn’t push anything. Tried not to message first. Let him take the lead.¬†I didn’t go into it with any expectations. I had to fight myself constantly to define and figure out. I asked poignant questions when needed for clarification but didn’t push anything.

So here I am… I don’t know what the future will bring but my good friend Jackie sent me this when I started dating and I have applied it to this entire adventure:


Don’t worry though… I still have a lot of great untold stories from before I met Jack, while Jack and I were friends, and all the mishaps I’m making now that I’m actually dating someone. I mean isn’t asking a guy daily if you’re still dating¬†totally normal?!


Can you drown in the deep end of the Friend Zone?

So over a year and half in and still single… like single… like totally single… in status. Why just in status? Well it depends on which part of me you ask. Ask my brain? I’m SINGLE… you ask my heart? It gets complicated. Yet another battle of mind vs heart.

That is because my friend I have been entered…pushed into the FRIEND ZONE and I can’t seem to get out. ¬†Now there is this idea that I have heard that the FZ is just a myth. One perpetuated by the media and by sad people trying to figure out why they can’t get a boyfriend/girlfriend. There is also the idea that the best relationships start out by being friends. That sounds great… on paper.

On many guys’ dating profile they write “I want to be friends first then see where it goes.” When I read that… ¬†I make a hard swipe left. (That’s the reject direction for all of my married readers). I ¬†know it sounds really romantic and always works in 1990’s rom coms…

However, I am a 34 year old mom (yes I hear that clock ticking too), homeowner, dog owner, career minded woman that barely has enough time to prioritize the things I need to. I have friends for life, that I don’t make enough time for (you all know I love you! we’ll get together soon I promise). So the idea that I am going to make it a priority to add another friend in the mix is not an option in my head.. or at least I thought not.

Now I’m going to find myself in a bit of hypocritical moment.. and yes I’m calling myself out on it. I’m more than happy to have a guy friend that I’ve dated IF I’M THE ONE NOT INTERESTED. Then we can be BFFs¬†all the way. If my heart is not involved I can be the best of buddies with people. I have many of these guys in my life. After all Some of these guys I actively dated and some were guys I went on a date or two with and we realized we’re friends.

These are the guys I ask life questions to:

What do you do when you run out of gas? Do you call the police? – This one wasn’t good. ¬†It started off with a friendly lecture on how to read my gas meter… ended with call a friend, preferably him.

What printer should I buy? – I DO NOT want to look through reviews.

Why the hell doesn’t this guy like me? I’m amazing!-¬†This one I like because if you’re my friend you probably think I’m amazing as well.. j/k I normally get actual practical advice on from this one.

Yet I find myself with a guy who started out with a different goal from both of us and now sees me as a “great friend” and is dating (not exclusively) someone else and it sucks! I find my normal black and white mind turning into a field of gray. Like drowning in gray paint.

I would imagine most people would just LOVE to have a guy that messages first everyday, randomly calls, remembers your coffee order, gives great advice, and is willing to go anywhere… I would too and I do..but I would enjoy it a lot more if it followed my black and white philosophy.

Instead I find myself questioning everything I do, ¬†contemplating ending conversations, becoming disinterested in the dating game, and not even giving other guys real chances. What I can’t figure out is… how do you open your heart to other people when¬†you have someone in there that doesn’t want in there?

Now the good news (because I always look for the bright side) and what I’ll probably learn from this situation is patience. I no longer get stressed out by no texts, timelines, and with labeling the relationship. I just really want to know that someone is open to the same goal as I am. Then we can take it from there.

So what is your philosophy on the friend zone? How long do you wait? or at what point do you realize that…