*Brady, 34- Part 2: Boundaries


Pros:

  • Charitable

  • Good kisser

  • Really fun

  • Flirty

  • Played the long game


Cons:

  • Playboy

  • Obviously wants to hook up


Alrightttt…….. picking up where we left off… The elevator kiss.

I couldn’t help but feel a bit giddy when I got home. The look on his face when I turned around and looked at him. He was in shock, but like, a pleasant shock. I mean- that kiss was a year in the making.

And the exciting part was…. we had a date the next day.

B: “(Martini Emoji) still on for 5 today?”

Me: “Yesss, see you then”

I ended up getting stuck in a meeting so I was a little bit late. He was already sitting at the bar when I got there- looking good as usual. He has lowkey salt and pepper hair and he’s always wearing a blazer. We hugged, and I sat down. It was all very chill. We were talking like friends because… we kinda are friends. The bartender recognized us from the night before, so we had a warm welcome and strong drinks. I jokingly said I shouldn’t have too many since I have to drive home.

B: “Well you don’t haveee to drive home. Good thing I live a few blocks away”

It was one of those half jokes. Like one of those things you throw out there just to see if it sticks.

Me: “Yeah not gonna happen.”

B: (laughing) “Had to try”

First of all- it ain’t that easy. Idk who he thinks I am (2012 me??)… but I was in an 8 year relationship. I’m basically a born-again-virgin.

And second of all- Yeah I’m gonna stay over at a guys place while I live with my Asian parents and get judged for the rest of eternity….. I THINK NOT.

Anyway- the date actually went really well. He was telling me about his company, how he raises capital for his clients, pitches to investors etc. And he’s pretty damn good at it, but I knew that already. I told him about the one time I did a little fundraiser for Sri Lanka, and how uncomfortable I felt asking people for money. I never even posted about it- I just went directly to my best friends and family because I was pretty devastated about how people were going hungry because of the economic collapse.

B: “And you didn’t tell me??? You know I raise money for a living right? That’s literally what I do. I would have helped”

Me: “I don’t know!! It’s weird. I didn’t really talk about it that much. I just kept it to close friends and family”

B: “Are you still accepting donations?”

Me: “No… I already sent the money”

B:
“Will you let me know next time?”

Me: “I don’t know if I’ll do it again, but sure.”

We talked about how much I raised, how I decided which charities to send to, etc. etc…. He was genuinely interested, curious, and really supportive.

B: “You’re pretty amazing”

Uhhhhh… Not even gonna lie- flattery works on me lol. But hello- I’m not stupid- guys say a looooot of sh*t when they wanna get laid. So my guard is still up. But… maybe I’m wrong and my judgment is impaired from my third cocktail… but, it felt like he started to think about me a little differently from just the girl he’s been wanting to bang for a year.

I learned a bunch of things about him that I didn’t know before. On top of starting his company, he started a foundation for veterans with PTSD- a cause he cares a lot about. I mean… anyone that does things to help other people is pretty cool in my book.

He’s hot and charitable….. OooOo I’m horny impressed.

We change topics. He was totally teasing me for not drinking with him before. Half of these work people either think I don’t drink at all, or am such a lightweight that I can only have one drink. I always skipped the happy hours I wasn’t required to be at. (I just kept my personal life and professional life sooo separate).

B: “Who knew you were so fun?… Best kept secret of the year”

Me: “Yeah, that’s the problem, I’m too fun. Had to keep it professional”

By this point of the night, we’re both super tipsy. He does this thing when he’s being flirty where he leans in super close and makes super intense eye contact, and talks like a few inches from my face. It’s honestly a little… hypnotizing. He’s like the snake in The Jungle Book, and my a*ss is Mowgli.

B: “Honestly, I never thought you’d actually go out with me. But, here we are”

Me: “You played the long game”

And what do you think happens next… he was basically a millimeter from my face. We start kissing… and damn, he’s very kissable. Once the kissing started, it didn’t really stop. The rest of the night was so fun. We kept talking and laughing. He was so touchy and flirty and cute. We stayed a bit longer to sober up. Chugged a few glasses of water.

It was getting late so he walked me to my car. Multiple pit stops were made. Honestly, it was just… fun. Up until this point, okay I kissed Brian, but I hadn’t actually like full-on made out with any of my dates. There was definitely chemistry there, and I was just rolling with it.

The next day he texted me.

B: “Goodmorning sunshine”

Ew cringe lmfao. I sent him the meme from Willy Wonka (Johnny Depp version)- “Goodmorning starshine, the earth says hello”

Me: “that’s how I read that lol”

B: “Lol… last night was fun, you’re wild”

Me: “Meeeee??? Wiiiiilddd??”

B: “Yeah, I woke up and I couldn’t stop thinking about *BEEEEEEEEEEEEEEEEEEEEEEEEEEEP BEEEEEP BEEEEEP BEEEEEEP BEEEEEEEEEEEP”

Oh shit, that’s definitely an inappropriate joke I made. Maybe I am wild.

We texted on and off after the first date. He asked me to meet up for post-work drinks a few times but I was actually always busy or tired. Then he texted me one day asking if I liked soccer.

Me: “Mmm.. yeah, I like it. But I’m not obsessed or anything. Why?”

B: “Well if I told you I had 2 tickets to a game would you turn me down?

Turns out his favorite soccer team (Arsenal) is playing in Baltimore and it’s a big deal for him and he wants to take me. I’m flattered- I mean, your fav team ever is playing here and you want to share that experience with me?… I like it. Plus, he got good seats. You think I’m gonna turn down a cool experience? I live for cool experiences.

A few weeks later my company hosted a networking happy hour, and of course, he came. I was actually happy to see him. It’s funny, I used to kind of avoid him and now I get kinda excited when I see him. After the event, we popped by a neighboring bar to grab a drink. The game was coming up and we had to discuss our game plan and logistics.

Me: “I’m soooo excited but what’s our plan!? How are we getting there? Please don’t make me drive” lol

(He’s a city person sans car)

B: “Yeah so I wanted to talk to you about that… No, I’m not making you drive don’t worry (laughs). I was thinking we’d take an Uber there… and let me know what you think about this- but, since we’ll probably be drinking and going out after the game, I was thinking of getting a hotel there. But I don’t want you to feel like I’m expecting anything to happen or there’s any pressure at all…”

Me: ….

B: “Gah, I didn’t know how to bring it up with you without making it awkward. I was even asking my friend for advice and I was like ‘dude, I’m going with a girl I haven’t slept with yet, I don’t know how to ask her without making it weird’ “

(Yet….? That’s a bold assumption.)

Me: “Umm… I don’t know… I don’t wanna be annoying so I really don’t mind Ubering back by myself. I think it’s just a little soon for me…”

B: “Okay no problem at all, we’ll just Uber back then. It’s totally fine. That’s why I wanted to ask you how you felt about it”

He was really, really nice about it. But I feel like I had to be honest and manage expectations so I wasn’t egging the guy on.

Me: “Listen, I really like hanging out with you, but…. I just don’t really sleep with people unless I really like them. I’m not that easy ;) You okay with that?“

Y’all… in my head, I’m the prize. Ya gotta work for it. And if you’re a girl that does hook up on a first date… you’re still a prize sis, live your best life. I’m not judging. I’m not saying I’ve never done it, and I’m not saying I’ll never do it again- but in general, that’s where I’m at. I guess as much as guys love the chase, I like being chased.

But more than anything, especially after coming out of a really long relationship, I just wanna feel comfortable.

Break backs, not hearts, people.

(Oops, there I go again with the inappropriate jokes.)

Dating 101 Key Take Aways:

Be true to yourself and what you feel comfortable with and what your boundaries are. If someone likes you, they’ll be okay with whatever you decide. If they aren’t okay with it, #thankyounext

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*Liam, 33- Ryan Gosling

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*Justin, 31- The Bad Date