AN: Hi everyone! I know I suck at updating (having to study for a promotional exam at work isn't helping) but here is another one shot that had just been running through my head the past few months.

The first thing Sarah Upton had noticed was that he was cute. Probably in his mid to late thirties and from what she could see besides the mask covering half of his face. Green eyes, light brown hair and she can make out a few freckles peeking out from under the mask. She was positive he wasn't a regular before the pandemic. Second thing she noticed was that he normally ordered on the healthier side of the diner's menu options.

"Here you go Jay." She said as she slid the two containers into the bag at the part of the counter now designated for pick up orders.

"Thanks Sarah."

"You need utensils?" Sarah asked and Jay shook his head no. "So second set of food? Girlfriend?"

"No, no it's for my brother. First time we've been able to have lunch since the pandemic. We've both been working the whole time."

"Well then this calls for celebrating. Have a piece of cheesecake. On me"

"No no you really don't have to."

"I insist." She said as she slid the package with the cheesecake into the bag. "Wish I could be spending more time with my kids during this so have fun with your family for me."

"Thanks Sarah." Jay said as he slid a few dollars into the tip jar.

Once indoor dining was allowed again Sarah was excited to be able to have the diner somewhat back to normal. Most of the loyal regulars from pre pandemic had at least come in once and today she noticed a certain new regular sitting down.

"Hey Jay."

"Hi Sarah."

She eyed the red haired man sitting across the booth from Jay. Taking in the resemblance between the two men. "So is this the brother? And what are we having today?"

"Yeah this is him and I think we still need a minute." When Jay shifted she noticed the magazine of a gun poking out under his shirt

"Sweetie your gun is visible."

"Oh shit."

"Good job." The brother laughed at him.

"So what are you? Chicago PD? Cook county Sheriffs? Fed?"

"Chicago PD." He answered with a blush settling in his cheeks.

Sarah lightly hit her pad against the side of the booth. "So is my daughter. I know there are so many of you guys but maybe you've met her. Have you ever crossed paths with a Detective Hailey Upton?"

Sarah noticed the brother seem to choke on his water for half a second.

"You know I think I've interacted with her a few times over at the hospital. I'm a doctor."

"Oh really?"

"Yeah she's on the shorter side with blue eyes and blond hair? Oh yeah then I've dealt with her a few times. She's a total sweetheart."

"Oh that's nice to hear."

"Yeah her partner can be a little grumpy but she's always so nice to deal with. And I'm going to have an iced tea to drink. Jay you want one also? So two please."

Once Sarah walked away Jay looked at Will. "I fucking hate you."

"So I was wondering why you liked getting food for pick up from here but didn't want to actually sit down and eat and now I know why."

"You had to bring up you knew Hailey now it's weird." Jay said with his voice just above a whisper.

"Oh yes, NOW this whole situation is weird." Will then proceeded to pick up the menu and look down at it. "I mean if I really wanted to make it weird I could of mentioned the med student with the huge crush on Hailey."

Jay's eyes narrowed at the new information. "Who?"

Will chuckled and looked up. "Jay, I'm kidding. Or am I?"

"I'm never going out to eat with you again." Jay mumbled as Sarah came back with their drinks.

Sarah set the final plates down as she waited for everyone to show up. The warm spring sun illuminated the table perfectly. A nice spring day that they were able to eat outside and her husband running the diner meant all three of her children had agreed to come over for lunch. A pick up truck she didn't recognize pulled up and when she noticed Hailey in the passenger seat she was extra delighted. Hailey had told her she had been seeing someone and Sarah had hoped Hailey would bring the new boyfriend to lunch so she could meet him. When Hailey told her mom she had started dating her partner she was skeptical but her daughter seemed happier than she had in a long time.

"Aww my baby girl is home." She exclaimed as Hailey stepped out of the truck.

"Mom, stop, being dramatic you're embarrassing me."

"I can't help it I miss you."

"Also Mom I would like you to meet my boyfriend Jay." Sarah looked and saw Jay from the diner standing in front of her.

"Oh Jay, so nice to finally meet you."

"You too Mrs. Upton."

"Please call me Sarah I feel like I know you already from everything Hailey has told me. You know what I think I need some help bringing the food out here. Jay, come give me a hand."

Once they were inside the kitchen Sarah turned and looked at him.

"So your brother may have interacted with her a few times huh." Sarah asked cocking her eyebrow.

"Uh yeah I guess I need to explain myself." Jay exhaled "I was walking home and I saw the diner. Hailey had pointed it out before so yeah I knew it was her families' diner. Figured I would get something to eat and help the business. Also helped that the food was delicious."

"Good subtle sucking up."

"Thanks. So kind of became a weekly thing. You guys aren't that far off from my drive home from work. Then I just didn't want to seem like a creeper that was buying food because he had a crush on your daughter."

"How long have you had feelings for her?"

Jay thought about it for a second. "A while."

"You love her?"

That he said without hesitation "So much."

"So we'll just keep this between us. Funny thing is I was getting ready to try to set the two of you up."

"Now that would have been funny." Jay said while grabbing the dish Sarah gestured too.

AN: Of course this is the part where I shamelessly ask for reviews. Please?