Usually when I travel for work I fly coach, but I got a free upgrade to first class on my flight back from Dallas on Wednesday. I love when that happens. I ended up getting a window seat next to this guy in a baseball cap and fleece zip up who was messing around on his phone as we were waiting for takeoff. I guess it was some sort of app to help manage his stocks because at the bottom it said he has a balance of like $10,000 and he was picking different companies (I saw Apple and Netflix) to put money into.
I sat there watching him because I was nosy intrigued and then he looked at me. Nothing like being caught looking at someone’s phone. I quickly pretended to be texting. The pilot turned on the seatbelt light indicating that we were about to take off so my neighbor turned his phone off and I did the same.
“Are you from Dallas or Chicago?” he asked me casually.
“Chicago,” I answered. “What about you?”
He nodded. “Chicago. Business or pleasure?”
I laughed and it was kind of an awkward laugh. Ew. “Business.”
“What kind of business are you in?” he asked.
So then we talked the entire two hour flight home. I gave a brief description about my job and I must have made it sound really terrible because he asked if I planned on doing that forever. So I told him about my new position and definitely hyped it up to sound super, duper important. Which it is I guess.
The guy told me about how he runs a really well known company in Chicago (I won’t say which one!) and I pretended I wasn’t totally impressed. He asked if I know stocks or if I’m into them at all and I admitted that I’m not so he explained it to me. I must have been too busy thinking about how rich he must be because I still don’t know anything about stocks.
Toward the end of our journey my new friend introduced himself as Matt. He was probably in his early thirties because he looked young, but he had a hat on so I could really look for any grays. He definitely has a sexy DILF kinda look. Matt gave me his business card then when we landed suggested we exchange numbers. I said okay and didn’t think anything of it. Never know when you may need stock advice!
Brady was busy with work and I didn’t get to see him until Thursday night after I had dinner with my friends Taylor and Elyse. Taylor and Elyse are like the knockoff version of me and Preston. I know them from college and they were visiting Chicago for Taylor’s birthday. I took them out for traditional Chicago deep dish pizza and pretty much spent the entire dinner telling them about my life. I didn’t even eat because I was too busy talking. In my defense though, I haven’t gotten a chance to really talk to them in like a year.
Brady texted me while I was in the middle of dinner and invited me over so I went over afterwards. It was our first time hanging out since Sunday and I really missed him. He opened the door and pulled me into a big hug and picked me up off the ground. Then we went to his room and I made him tell me everything he did over the week. He mentioned that he talked to his mother and she said there was an opening at the hospital she works at so he should apply. Like in Massachusetts. I always forget that Brady’s mom wants him to move back home (even though she doesn’t even act like she likes him) and sometimes he entertains the idea.
“Did you tell your mom we broke up?” I asked suddenly.
“Uh, yeah-” Brady said.
“What? You did?!” I was kind of offended. Like yeah we broke up, but did he not think we’d get back together? Why would he tell his mom unless he thought it was permanent?
“I kind of had to. She wanted us to go to Florida with her and my dad for Easter.” Brady was looking everywhere except at me, awkwardly.
“What did she say? Was she happy?” I asked.
“No. She just wanted to know what happened and if I was okay with everything…”
I felt myself wanting to say a lot of really unnecessary shit like, “She’s probably happy and wants you to get back with your doctor ex-girlfriend,” and “I’m sure she wants you to be unhappy because she is.”
But instead I said, “My mom likes you so much that I didn’t have the heart to tell her.”
If Brady and I are going to make this work then I need to be a better girlfriend. This includes getting along with his mom so I guess I need to be nicer.
Kate called me on Friday morning.
“Reese!” she said hysterically in her British accent. It sounded like she was rushing down a busy New York street. “I just spoke with Andrew. Why didn’t you tell me you were leaving?”
“I’m so sorry! I meant to tell you!” Which was true. I wanted to let her know before I even told Andrew since she was nice enough to get me the job, not honestly I just completely forgot.
“What happened? Is there something we could have done differently?” Kate asked and it made me feel really bad. I don’t mind screwing Andrew over, but Kate has been nothing but sweet to me.
“No. It’s nothing you guys did at all. I just really don’t feel like I’m doing very well here. I got a really good offer from the last company I worked for and I loved my old boss,” I said.
“Did you not have a good working relationship with Andrew?”
“No, I did!” Oops. I didn’t mean to throw shade at Andrew in the process. “I just don’t think it’s a good fit.”
Kate said she understood and that she wanted me to know that she isn’t mad, but I definitely feel like an ungrateful bitch for not talking about it with her.
I also heard from Matt on Friday. My old stock market friend! He texted me letting me know that his company is having a pub crawl (on them) at some bars around the city and I was welcome to come with any of my friends. It’s next Friday night and obviously I told him that I would be there.
On Friday night, I went out with Taylor and Elyse. I needed to show them how we party in Chi-Town. We were drunk before we even left their hotel room. So by the time we were ready to call it a night I was trashed and wanted to go see Brady. He didn’t answer any of my texts so I called him after we left the bar. It went straight to voicemail. Being the drunk mess that I was, I started bawling.
“He’s cheating on me!” I cried. “We haven’t even been back together for a week!”
“His phone is probably dead,” Elyse suggested.
“Dead?!” I screamed. “How would his phone be dead if he’s at home?”
Luckily we got back to their hotel room and I passed out on Taylor’s bed on top of all his clothes and shoes. I woke up on Saturday morning because my phone was ringing. It was Brady.
“Oh hiiiiii,” I answered, rolling over and puncturing my hip on a boot.
“Hey. I’m sorry, I was sleeping. Are you okay?” he asked.
“I’m fine. Why?”
“Your text messages were weird last night…”
Oh shit. I had no idea what I texted him so I told him to hold on while I went back and looked. I’d sent Brady about a dozen or so text messages letting him know how disappointed in him I was and how if he wanted this to work he needed to call me at his earliest convenience. There was one that said, “URGENT 911!!!!”
“Oh sorry about that,” I said into the phone. I was actually pretty embarrassed. I’m trying not to be a psycho girlfriend this time around, you know? “How was your night?”
“I was pretty exhausted so I went to sleep early. How was yours?”
“Pretty much the same. I miss youuuuu! Come get me?” That’s when I realized I was still a bit drunk from the night before. #signsofagoodtime
Brady said okay so I jumped up to try to make myself look more presentable and less like last night. I washed all my gross makeup and mascara off and pulled my hair into a chic half up messy bun.
“Heyyyy boo!” I said when I met Brady downstairs. I jumped in the car and kissed him on the cheek. “I’m starving. Can we get food?”
I was hungry, but not presentable enough to actually go somewhere so I had Brady stop at a McDonald’s drive thru. McDonald’s has these new muffins and I definitely recommend them. I got three. And three hashbrowns.
On Saturday night, we hung out with Carly and Chris for a bit. Then I got bored and started yawning really dramatically to get Brady to go to his room with me. We still hadn’t had sex and I was feeling frisky after three glasses of wine.
We got upstairs and I started kissing him. We made out until he flipped me over and pushed my top up. I almost squealed with excitement. He planted kisses down my tummy and hooked his thumbs under the waistband of my undies. Damn, I miss Brady going down on me. But then he stopped at the top of panties then stood up.
“I’m going to shower,” he announced.
Ugh. He must have went in there to jack off because when he came out he just wanted to snuggle. Like, okay. Guess I’ll just be horny.
Brady and I woke up early on Sunday. We laid in bed talking and I convinced him to download Instagram. Then I took his phone and picked a username for him, followed myself and no one else, linked it to his Facebook then uploaded his first picture: one of us looking hot from the wedding.
We got up and went for a run then went to Starbucks (can we be any more white?). Then spent the day sitting next to each other at the dining table with our laptops doing our respective work. Even though I still have another week left of working for Andrew, I just thought up ideas for my new office instead of doing any actual work. Priorities.
I asked Brady if he planned on telling his mom that we are back together.
“Umm, I don’t know. Should I?” Brady said not looking up from his computer.
“Maybe. Just in case she wants to hook you up with someone else.” I laughed loudly, but Brady didn’t say anything.
“Does your mom do that? My mom used to. She gave my number to like all of her friend’s sons. And all of her friend’s friend’s sons. Basically whoring me through the suburb,” I blabbed.
“And none of them were to your liking?” Brady asked, still not looking up.
“Well they’re not you, so no,” I said sweetly.
He finally looked up and smiled at me.
Later that night we were laying in bed and I saw that Brady had some comments on his Instagram picture. People were like, “Who’s the lady?” and stuff like that. I think it’s weird that some of his friends don’t know me. Even my friends back home know who he is and what he looks like and stuff. I’m going to tell him he needs to show me off more even if it’s online.
As we were laying in bed on Sunday night I got a text from Matt. It said, “How was your weekend, gorgeous girl?”
I smiled and said,”It was so much fun!”
He asked what I did and I told him about going out with Taylor and Elyse. He said that I should have told him that I was going out because he would have gotten me and my friends free drinks. Apparently he can just do that? Matt mentioned that he wants to see me this week and I told him that I’m really busy which I am. I probably should tell him that I have a boyfriend? I never know when to include that in conversation. Plus, I don’t want to burn my bridge with him. Is that awful? I just want unlimited free drinks!
hot mess in high heels. 
Take this with a grain of salt, and know I’m definitely not trying to lecture you or make you feel bad: if you want things to work with Brady, stop with Matt. I think you would probably be really mad or hurt if Brady was doing something similar with a different girl. I know it can be really hard to break off those flirtatious whatevers (not really friendships, but like, dudes who give you attention) because I had a tremendously difficult time with doing the same thing, and it’s still hard, but it really does help to make a relationship work.
That’s probably one of the hardest things to do! It’s nice getting all that attention 😩
so trueeee
okay you’re right. so I can’t go to his pub crawl? 😩
I would totally tell this guy you have a boyfriend so he knows what’s up. Then, bring Brady to drink for free at the pub crawl. 🙂
Reese! I agree with the comment above – you would be pissed if you found a message like that on Brady’s phone. I think flirting is fine but you gotta work the bf into the convo somehow otherwise this Matt guy is just going to keep texting you… And it won’t end well.
okay if I talk to him this week I’ll be upfront about it.
I totally agree with the above comment. If you and Brady’s roles were reversed, you would be furious.
That being said, I also think that you and Brady need to have a serious talk about the state of your relationship. Are you two really back together? Where does he see this going? Is there some reason he is avoiding sex with you? Is he going to try for the job in Massachusetts? If so, what if he gets it? Would you go with him? Before he broke up with you, you two were talking marriage. Is that back on? Who knows you broke up? Do these people now also know you are back together? It sounds to me like he is holding back emotionally, as if he is afraid you are not all in and might bolt on him. Ironic, I know, since this mess is all his. And lastly, what does he want from you? If he is not serious about working things out, then he is just messing with you and that is not right. Add to that you two have yet to work out your communication issues. I know you love him and hate confrontation, but you need to get all this out now or you will likely get hurt again. He is being just as uncommunicative as he was before and that is not sustainable. If this new try together is not going to fly, better to find out now.
I am pulling for you two, but if he is not serious, you need to know because you may miss out on someone else who may be. All your friends seem to be coupling up for the long haul and I think you deserve the same thing. Time for an upfront DTR.
I think you bring up really good points, as usual. I didn’t get the impression that he planned on trying for the job in mass but he also never said he wasn’t going to. but you’re right. we have so much we need to still talk about.
Yes! ^
Holy Hypocrite, Batman.
….me?!
I 100% agree with everyone’s comments. STOP! CEASE! DESIST!!! You are doing things you would castrate Brady for and it’s NOT ok.
PS: I do NOT agree with the second half of Sarah’s comment though. LOL Just the stuff about Matt the broker! 🙂
but seriously, what am I doing?
Some I’m sure most people will disagreed but why not
Continue with Matt, Brady’s not even sure he wants to tell his mom you guys are seeing each other again. You’re making all these efforts to make this time with him different and he’s falling back into old habits. You’re young have fun and live life!
😳
I agree with what everyone is saying. It seems like Brady is falling into old habits. I think you need to have a conversation. 1. Are you back together officially? ( I know he introduced you as his gf since the wedding but have you guys talked about it since then?) 2. I also think you need to discuss what y’all will do differently to make things work this time otherwise it would be same old. Y’all need talk about what your expectations are this time around and maybe address how you will deal with your communication issues. 3. Jump his bones or ask him why he’s holding out on you. He can’t do the same thing all over again
I can already feel that things are different this time even if we haven’t talked about it. I think we both know what we need to work on but I do want to have a real conversation about it.
I think it’s hypocritical for you to give your number to Matt and text him. You keep saying you love Brady and want to work it out but your actions say otherwise. I think you and Brady have issues you need to discuss. You’re adults. Sit down and communicate. You both need to make sure you’re on the same page. I feel and I can be completely wrong that you like the idea of having a boyfriend and not necessarily brady. You know having someone you can come home to and hang around. Even when you two were broken up you found comfort with Kyle. I think you need companionship and don’t like being single and might be clinging to Brady because of that. I might be wrong and I hope my comment doesn’t offend you.
I couldn’t disagree more, kelly. Matt and I haven’t talked about anything sexual or romantic so I’m not sure how that is hypocritical in any way. and I do like having a boyfriend, but I like Brady more. if I just wanted to have a boyfriend and/companionship then I could get that anywhere. I deal with Brady because I love being around him.
He called you “gorgeous girl”. He wouldn’t say that if he wasn’t flirting. Give up on monogamy with Brady if you’re not mature enough to be emotionally faithful to him.
oh please. I’ve always been emotionally faithful to him. don’t try to make me feel bad, he cannot say the same about himself to me.
I agree with Shelby. You keep saying you’re cool with Brady having female friends but have shown how jealous you are in the past. If Brady gave his number to a beautiful woman and she texted him hi handsome you’d flip out and break his phone again. You are controlling and have no issue putting Brady in uncomfortable situations. I don’t know how emotionally faithful you are knowingly giving your number to Matt and thinking about going to his pub crawl. You want a relationship but also want to be out and about cavorting and flirting with random men. You can’t have it both ways. And FYI if you care about Carly as much as you claim you need to tell her you hooked up with her brother. It wasn’t just a one night stand. The truth will come out and bite you in the ass. You expect loyalty and honestly but don’t give it. Be a grown up and take responsibility for your choices.
are you kidding? I don’t want to flirt with random men and I don’t want anyone except Brady. I exchanged numbers with one guy with no intention of a romantic relationship. i wouldn’t do that to Brady and I can’t believe you guys think I would. I’ve never been unfaithful to him whatsoever – at all. I’m offended.
Reese you keep saying you love Brady and only want to be with him but you’re actions don’t match. You’re not clueless and know how to pay the game. This whole i gave him my number because i might need stock advice is bs. You clearly admit he’s hot and then his text shows he’s interested. There are plenty of times when you were with Brady that you’ve admitted to flirting with men at the bar, getting free drinks and so forth. You can pretend to be the sweet, perfect, loving, understanding girlfriend but you weren’t most of the time. It’s always been your way or no way. You never give Brady a chance to be his true self.
what the hell? I’ve always given Brady a chance to be his true self. I know I’m not a perfect girlfriend but I would never do anything with another guy behind Brady’s back. you guys are being crazy.
and obviously I probably won’t ever need stock advice but i don’t understand why i should feel bad about talking to him. I would tell Brady what happened and let him read our text exchange! it’s not bad.
It isn’t that bad? How would you feel if the tables were turned? You’d go insane. Brady won’t mind? Huh? It would be interesting if Brady reacts how you would if he gave his number to a woman. I doubt you’ll tell Brady anything. You’ll brush it under the rug like always and if you do tell him and he gets mad then you’ll turn it around on him being the jealous time.
I don’t mind telling him at all. and he definitely won’t be mad because there isn’t anything to be mad about. so that won’t be a problem!
Can y’all chill out. She hasn’t crossed any lines. She met a guy and they exchanged numbers. So what? She’s an adult and he could be a good network. Obviously now that he’s called her gorgeous girl we understand that his intentions may not be pure. We’ve told her to be careful and let him know she has a boyfriend. I think that’s it. Reese hasn’t crossed any lines. It’s not like he’s asked her out and she said yes. I say if he makes a serious move you politely let him know you have a boyfriend. As for the bar crawl, go with your friends or don’t go at all. It’s your call. I don’t think you need to tell Brady anything. As for y’all judging her, chill out. If Reese does anything shady we’ll let her know but I don’t think we’re there yet.
Ahhh I wish you met Matt before you got together with Brady. I think everyone’s being a bit harsh on you with Matt, but yeah you have to stick the bf into conversation somewhere. 🙂
true! he could be a good catch
Seems like Matt has connections all over Chicago lol… He seems like a cool guy but I am always rooting for you and Brady 🙂 Hopefully you’ll have a chance to talk about your issues and everything will be better this time around!
Matt sounds interesting. I don’t necessarily think you’re doing anything bad so…
As long as shit doesn’t get flirty. But you’re a big girl. You know what you’re doing.
Happy for you and Brady. Sounds like you’re gonna be having #cheeseburgerpenis soon 😉 or not soon? idk. lol
or just a cheeseburger?! lol
If you want to see where things go with Matt, you have to drop Brady. If Brady were having “non sexual innocent” contact with another woman you would flip your shit. We all want you to be happy, Reese. But you need to either work things out with Brady or move on…..and maybe see where things go with Matt or someone else. I am team Brady. You are both so closed off and oblivious. There’s no shame in being the initiator. Just do it! If you really love Brady go for it. Best of luck to you, doll!
I don’t care about Matt. I don’t know him at all and I’m not going to ditch Brady to see where things go with him. I didn’t do anything with him and I have no desire to so I don’t know why everyone is jumping to conclusions.
…girl. lol because you acknowledged in the post that you know his intentions aren’t 100% innocent and you didn’t cut him off. this guy just met you and he’s offering to buy you and your friends drinks wherever you are. being realistic, he’s not doing that for every random person he meets-he’s interested and you know it. if brady met a girl somewhere like this and gave her his # and she was trying to meet up with him or buy him drinks or whatever else you would FLIP SHIT.
omg no I wouldn’t. Brady is allowed to have (and has!) female friends.
plus Matt hasn’t expressed any romantic or sexual interest in me at all. calm down.
Hey! So assuming based on your twitter that you chatted with Brady some, I think you really do need to be careful with this Matt situation. I know you say you wouldn’t be mad, but I kinda disagree (sorryyyyyy). Do you have any single female friends? Set Matt up with one of them!
If you didn’t have an honest chat with Brady, then all bets are off!
I think two things: 1) Matt is flirting a bit (but just a bit), but also 2) I don’t think people should be running with the whole “Reese and Matt” thing. You guys are practically picking out china patterns and bedding sets. Calm down. I mean, a couple of texts? Lighten up, folks. Yes, Reese should be circumspect in contacting him to avoid seeming hypocritical (as I stated in a previous comment), but it’s not like they are doing the wild thing behind Brady’s back. My only reservation is that being back with Brady is so new, best not to ock the boat until things are settled. Matt sounds like he does have connections and that might be useful at some point from a business standpoint. And a pub crawl sounds like it means lots of people. It’s not a one-on-one date or anything. Hell, Reese could go and bring Brady with, for that matter. So let’s not make it more than it is. Just saying.
And that would be “rock the boat”. Obviously my typing skills are not on point tonight.
Unless it comes up organically in a conversation, you’re not obligated to work into a random first convo with a stranger that u have a significant other. We can’t all go around assuming in life that everyone automatically wants to bang every member of the opposite (or same) sex that they have any interaction with. Your meeting with Matt on the plane seems pretty harmless to me.
Of course, Matt has texted since then and called u gorgeous so it may be safe to assume that he is interested in u, so your having a bf may have to be gradually worked into a conversation soon! Just to be safe …
From what I remember reading about Brady’s parents, u were nice and made an effort and they were both horrible to u Reese! They never gave u a chance at all so they need to be nicer to u and hopefully Brady will support u …