Elena's almond eyes rolled at him as he had rejected another one of her 'babysitter' suggestions. "So when is your magnificent babysitter coming in?" she asked with a loud huff sitting on the opposite sofa, she pulled out a nail color which had previously gone unnoticed to him. "Any minute now," he looked at his wristwatch for a second. "Zach is an expert in the whole baby department and he says he's sending one of the best in the game here," his tone a little proud. Elena raised a brow, "Isn't Zach your uncle- the one who forgot his kid at Disneyland?"

"Oh but that-"

"And the one who didn't realize his son Eli had crawled into the washing machine, oh and when your walnut allergy nearly-"

"Okay maybe he's not an expert but he says this babysitter is amazing," Damon assured. "Plus he said she's hot."

"Oh, Damon that's tragic," she said in a condescending manner. "Ugh, you're gross." She got up from the sofa and went to her room across the hall, he impersonated her expressions silently, "Nag-Nag-Nag! Jealous little-"

"Honey?" Rose walked into the room and he threw his head back to look at her, "Here."

"Ahuh." She walked over to him, her hands on her hips, "Is Elena going to stay over tonight?"

He shook his head, focusing back on his laptop for finishing touches to his project, "No, she said she'll go for the date from here-then she'll pick up the kids and go home."

"Why are you bummed about her going?" she asked when she detected the bitterness in his tone, he shrugged, "Well because I don't want any Tom, Dick, and Harry in her life- that's going to affect my kids too."

"But she's just dating," she sighed and sat down on the sofa in the place Elena was previously sitting in, "You sure you aren't jealous?"

He narrowed his eyes as if indicating how absurd the statement was, "Oh yes, I am very jealous- come on Rose."

"Okay, okay," She held up her hands in surrender and got up, "I am gonna get ready too, Can you please not look like a rat on date night."

"Okay sure, I'll get a shower as soon as I am done here." He said focusing back on his work. Both the kids were fast asleep after they came back from school. That's what he actually loved about their school, the kids were so tired when they came back usually and they sleep for at least two hours.

With the house bell ringing, he immediately got up, Elena too came running out of her room, "Hurry get the door before the kids wake up!" she exclaimed. He nodded, running for the door but when he opened the door- his anger rose, some high school kid was standing at the door, dark brown hair and sharp hazel eyes, built a bit but not too tall. "We aren't interested in buying any protein bars," he nearly shouted at the unwanted guest.

"I am not selling protein bars," he said seeming a bit offended. He was carrying a big bag which made Damon think he was 'selling' something.

"I don't want to buy anything." He said clearly this time, Elena too stood by his side. "Yes please- and one single bell does it buddy- tip for next time."

"Wait what? I am not selling any product. I am the babysitter," he said with wide eyes. Damon looked at him from head to toe, "You're a guy?"

"Great," Elena chuckled reaching for his bag. "Please come inside."

"No-No wait," Damon kept him outside. "We need a second." He slammed the door shut and turned to her.

"So?"

"Zach didn't say he's a guy."

"Well did he say he's a girl?" she asked with pursed lips. He shook his head, "No, but he called him hot."

"Oh, come on! Zach's been separated from his wife for twelve years. There is a reason he doesn't have a girlfriend yet."

Realization dawned on him. "That's traumatizing. Isn't he too….young for Zach?"

"Now I know why your Dad hates calling him here on Christmas," she gasped.

Elena opened the door and let the boy in, "I am sorry about that- let me tell you some things about the kids."

Meanwhile, Damon stood there and was recalling some more weird uncle Zach moments.

(-TVD-TVD-TVD-TVD-TVD-)

Go figure, his daughter was up from her 'nap'. Elena was waiting for her date while watching the TV with Rachel in her lap. When he had walked into the room for a second he had stopped in his tracks. She looked absolutely stunning. She was wearing a pastel green dress that ended above her knees. Her legs were miles longer than usual in her lightly dazzled pumps, her hair was in loose curls framing her beautiful face.

"DADDY!" Rachel called from the couch. He immediately straightened up as if doing some sort of damage control. Hopefully, Elena didn't catch him gawking. "Are you going to Mommy's party?"

Oh, his sweet innocent daughter thought her mother who was a wolf in a sheep's clothing was going to some party? "Umm No… Mommy is going to a party and Daddy is going out with Rose." He corrected her and sat down on the couch beside Elena, resting his hand on his daughter's knee, "Where's the nanny?" he asked Elena.

"His name is Brooklyn." She said in a bit condescending tone. Damon frowned, "Oh now I know why I thought the nanny was a girl."

"Well, the nanny is with your son at the moment. He didn't do his art assignment and Brooklyn was kind enough to offer help." She huffed, "Because I was doing my makeup."

He couldn't help but feel a bit of a victory at how bitter she sounded all day, was it because she was going on a date? Was she jealous? Why did he care again? The whole thing infuriated him.

After almost two minutes of silence between them and Rachel bumping her head against his shoulder, Elena asked, "So where are you taking Rose?"

"Hmm, we're going to 'A Mano'. It's a long drive too so-"

Elena interrupted, sitting forward a bit, "Wait- isn't that the restaurant we wanted to go to? A few years back- that's the same place isn't it?" she narrowed her eyes.

"Yeah but-"

"God Damon, you are so petty." She placed a confused Rachel aside and got up seeming a bit furious, "You know I love that place. I showed you that place. I was the one who wanted to do the whole valentine's day date there."

"Yeah but you were also the one cutting contact with me before that." he hissed. She shook her head, "Wow! How many times are you going to grab on to that straw, get over it, Damon."

"Mommy, why are you being so mean!?" Rachel demanded. It was rare seeing her cool-headed Mom getting so annoyed with someone, especially her 'perfect' dad.

"Yes Mommy, why are you being so mean about something that isn't about you," He too said in a snappy tone. Elena clutched her fists, she didn't want to choke him to death in front of her child, "I know it isn't about me but how can you replicate what I want into what you have, don't you think that's a bit disrespectful towards what our relationship was."

"No, I don't because being so dramatic over such details is very stupid." He said in a bit loud voice which made her shiver for a second. Rachel gasped and jumped down the couch standing between them, "That is not nice Daddy, you are being double mean!"

"Calm down, angel," Elena sighed seeing how Rachel was getting emotional, she sat down beside her, wrapping her arm around her, "Mommy is joking okay?"

"This is not a fight?" she asked, now very confused. Elena shook her head, "Nope, Mom and dad are best friends. Right, Damon?"

Now that Elena brought it up, he was feeling embarrassed to be even arguing slightly with her in front of their kid, "We are." He too sat down beside her and cupped her small face, "Is Rachie worried?"

She nodded, "Just don't be mean to Mommy. When she starts crying she doesn't stop."

"That's not true." Damon chuckled. He knew Elena had this superpower of not crying in the most heart-breaking situations. Elena rolled her eyes as Rachel got on her toes, all excited to prove her point, "No! No! it is! Mommy cried so much at the Hachiko movie!"

"That's enough Rachel," Elena sighed and pulled her from Damon. "Come on, I'll make you a snack."

"A grilled cheese?" she asked excitedly?
"No." she huffed and held her tiny hand leading her to the kitchen. Damon pressed his lips together and got up, he didn't want to shout at her like that but lately he was easily offended at whatever she said. He didn't understand how he was in the wrong here but still, he felt like he needed to apologize. He walked to the kitchen and saw her cutting up potato slices. His daughter was sitting on the opposite counter, on seeing him she stuck out her tongue at him. He raised his brows at her, putting her hands in his pockets, he walked to her, "What are you doing?"

"Baked fries, she loves them," Elena said not giving him a look. He shared a look with Rachel where she was mouthing something which he didn't quite catch, "Elena, look I didn't know it was a big deal, I mean I know we liked that place and you showed me it but isn't it-"

"Ahuh. I get it now, I don't know why it should mean something to me." she said chopping it faster, "Who cares if I never went there, never had a perfect date, don't have a fiancé and am evolving into a super soccer mom."

He sighed and put his hand on her shoulder, "Okay easy on the slices, you want me to take her somewhere else?"

She turned her face towards him, a fierce look in her eyes, "No. Do as you like." She shrugged, "I don't need your pity okay? Actually, I am going to have a lot of fun on my own with Kai tonight, it's probably going to better than the awkward dinner you're going to have." She pouted and moved towards the oven, "Maybe Kai will show me something better than that place I showed you, it will be better than getting soaked in the falls and eating hot Cheetos."

His mouth dropped open, it was the most painful of personal attacks, "You loved that, you called it an ideal date."

"Oh come on Damon, I said that to make you feel better about your minimum effort" she said in a sassy tone, "Minimum effort? I was saving up for a guitar."

"Right, you gave me a charm bracelet and coupon of 'love' on my birthday, that was two months after you bought that stupid guitar." She said grabbing some carrots and chopping them, "Elena that's not fair, I took you to Aruba six weeks from that."

"How can I forget the place where the food you bought us gave me food poisoning." She gave a sweet smile that felt like she was twisting a knife in a wound.

(-TVD-TVD-TVD-TVD-)

Rose was looking all over with amusement, her curls framed her face so well, her lips were coated in red lipstick, a small amount of blush over her cheeks and she was wearing a black bodycon dress. Damon was studying the menu a little too seriously, his mind still circling around that comment, "This place is nice right?" she said in a whispery voice to him, he looked up and nodded, "Yeah it's good. A bit mm-"

She completed, "Boujee." He gave a grin and looked back at the menu, "They have a lot of ways to say pasta and soup in here."

"You complaining about what?" she chuckled and leaned forward to hold his hand, "So what's the special thing you wanted to talk about?"

"A lot of things really." He put the menu down and bit into his lower lip, "We should order first."

"Ahan." She nodded and tucked a loose strand behind her ear, "So Elena's going to take the kids home today, no one will be home." She said with a mischievous look on her face, "We will have the place to ourselves."

He didn't study her expressions very well, the mention of her name made him think, what would she be doing right now, Kai had picked her up just before him, she was looking like a damn fantasy tonight. Kai had her all to himself for the next few hours, he would easily surpass the 'Cheetos' date. Why did he care again, he was here with Rose, yes he needed to be present. "We should have some Cheetos."

"What?" Rose asked, "I mean the lobster- it looks a bit different." He instantly corrected himself.

"Um yeah ok, I want to get a lemon chicken though." She said. "So we have the place to ourselves we should take advantage of that shouldn't we?"

Now he knew what she meant. They both hadn't had sex ever since they got together again, Rose was probably expecting it. "Sure why not, by the way, umm do you think a date in the falls is cheap?"

She frowned and looked up, "Date in the falls?"

"Date in the falls, near the bridge- just with a bit of junk food like Cheetos, the rain ruins it but somehow it turns out kind of romantic?" his eyes begging for a vote in his favor, she looked down at the table as if thinking, "That is pretty romantic if you think

"I know right, she was totally trying to screw with my head." He blurted out accidentally, just when he let those words out, he realized the situation, Rose wasn't his friend, she was his Fiancé. His eyes widened a bit when he noted the change in expression on Rose's face, "Who are you talking about? What date?"

"Caroline, Her and Stefan fought-again."

"Oh, aren't they over yet?" she asked seemingly bored with the drama but she was very invested in Caroline's life. "They are but you know how Stefan tries to get together with her again, she recently mocked him about a teenage date." He inserted his own frustrations into it, "Stefan says Caroline loved the date, and look at her now being all I-hated-the-date." He imitated her squeaky voice, "She's like the nicest girl in the world but is a real bitch sometimes."

"You're really that worried about Stefan?" Rose asked a brow raised, he huffed, "Stefan did his best in that relationship, he was a good boyfriend. If she didn't 'like' the low-budget date, how come she jumped his bones after it." he said with a bit of enthusiasm which was very strange to Rose, "Did he tell you that?" Rose didn't want to imagine that date or Stefan and Caroline doing….things.

"I just know it." he let out a sigh wondering how Elena's 'perfect' date was going.

(-TVD-TVD-TVD-TVD-)

"I didn't know this would be so casual." Elena had worded the same sentence in different ways for the umpteenth time. Kai didn't really seem to care or didn't actually realize it. They were at a small diner called Freddy's. Elena had never been here so it was probably opened after she moved, but she felt like she was over-dressed for the situation. This seemed a lot lower than her expectations. Kai had ordered double cheeseburgers for them. There was a birthday going on in one booth. It was a total worse than McDonald's scenario. Now that she saw things closely, Kai was a bit of an economical opportunist as she liked to say it, in Damon's words a cheapskate. He wanted to save on everything and anything. She would never tell Damon that Kai picked up a few extra straws in addition to the free ketchup sachets. She was honestly a bit embarrassed here all dressed up and done for this. "It's liberating in a way, we already have so many meetings in big hotels, it gets exhausting, the formal environment right?" he justified his choice.

Elena nodded picking up a fry and eating it, "I haven't eaten unhealthy in so long, ever since Rachel's diagnosis, her Dad and I are trying to make clean eating a habit." She said picking up the burger and taking the bite, "Isn't it weird to be living together?" he asked.

She shook her head, "It's not for most of the time, we are good friends, he's a great dad." She had to admit that, he accepted the kids so quickly and they bonded so naturally with him. Damon had once claimed that he could never be a good father but Elena knew he was underestimating his abilities once again. Maybe that's why she mad at him, Damon had it all. He was an effortlessly good parent, the kids loved what he cooked for them, they loved to talk to him before they slept, he was going to get married to Rose. Everything in his life was okay. Was she jealous of his perfection? He was probably having the time of his life right now.

"He is taking the dad role a bit seriously, he's a new dad after all," Kai commented, Elena had noticed, he didn't really like Damon and she knew it wasn't because of her, it was because of a previous accident between them, in which they fought over car damage. "It's been months, I don't think it's a hobby at this point, he's good at being a dad."

He just shrugged it off, a few more Damon bashing comments and she was getting the idea that Kai really wanted Elena to be on his side so they could hate on him together. "Why did you two break up?" he asked all of a sudden, she just shrugged, "We didn't break up we just were in long-distance and eventually stopped talking."

"And that's when you were pregnant? Wow, he's a coward for abandoning you." He said with disgust. She bit her lip with embarrassment confessing, "He didn't actually, I stopped talking to him. I was just unsure about all of it."

Perfect timing, they were given the check, that's when her actual nightmare started, Kai starting a rant about 'recommended tip'. How his consumer rights were violated with this sort of terms on the bill. Elena could feel the heat burning her ears up to her cheeks, the few people from the booths were watching them. She knew Kai was an 'economical opportunist'- heck he was damn cheapskate but could he not tone that down to a normal level instead of making them something people might write essays about on their Facebook pages.

When they were driving back to the house, she was still clutching the seat in the car cringing at the argument kai had with the manager and waiter at Freddy's! Fucking Freddy's. Now she was thinking about the argument Damon and Kai must have had all those years ago, where Damon established the opinion of Kai being the way he is.

"You can pick up the kids, I'll drop you home." Kai offered, Elena couldn't even take another moment of Kai now, No way in hell was she agreeing to that, she realized something Kai at work was very different from Kai in real life, At work, he was friendly and dedicated to his job, he was helpful too. In real life was ….very unlikeable. She wondered if the higher bosses knew Kai's extreme debate skills at public places. "Oh it's fine, Damon and his fiancé won't be home. I can stay with the kids since the house won't be locked." She made up a lie, as the car stopped, she picked up her purse and headed for the door when he held her wrist, "Elena, hey hold your horses." She was cringing now, Did Kai want a kiss or something because right now wasn't a good time, she was very embarrassed and done with this nightmarish date where all she did was hear trash about her ex, eat at a very kiddy-meal place while dressed like she should be on Paris fashion week otherwise- maybe that was a bit of exaggeration and even later when nothing more could go wrong, Kai started arguing with the staff over the tip. "You forgot your coat." He said reaching into the backseat and handing her the coat, she sighed of relief and nodded her head taking it, "Thanks, I'll be going now."

"Yeah just Venmo me the money for your half." He said starting up the car again, Elena looked back with a raised brow, "Umm, are you talking about the food we just had?"

"Yeah." He nodded as if it was no big deal, "It would be 8 dollars if you didn't order the ice cream so like 10."

Elena pursed her lips in anger and nodded, "Okay, sure. Bye," she said getting out and shutting the door after her, walking as fast as she could to the boarding house, tears of anger pooling in her eyes as she opened the door. She threw her coat on the couch and stepped out of her heels, Brooklyn was watching TV, on seeing her, he closed it and stood up. "Mrs. Salvatore, you're home about an hour early."

She let out a huge sigh, collapsing on the sofa, "I can't imagine being on time, are the kids okay? Are they asleep?"

"Yes, we painted, then we played a little hide and seek, I gave them dinner and now they are asleep." He said innocently and grabbed a blanket from the side handing it to her, "You look exhausted."

"I feel like I am." She said palming her head, "Wait a minute," he said and rushed out of the room, She was even tired to look up and just cuddled back in the sheet trying to forget the humiliation she just faced.

"Here Mrs. Salvatore." He handed her a cup of tea, she looked up from the blanket and grabbed the hot cup, "Peppermint tea." He said and sat down by her side, as she propped up a bit to sit, "Thanks." She smiled taking a small sip, "FYI, I am Miss Gilbert."

"Oh, I thought you were married."

"Nope-nope, Damon and I are just friends." She said and took another sip, then noticed him look a bit weird at her, "I mean we once dated now we just co-parent, hence the different dates." She clarified, he nodded, "Oh, yeah I thought you guys were a bit weird."

She giggled and shook her head, after a long moment of silence, he asked, "So how did your date go?"

She shook her head, "It was awful." Her voice a bit raspy, "Damon was mocking me about Kai and he was right," Her voice sounding a bit disappointed, "He and Rose must be sipping champagne and I downed a sprite zero because it was a dollar and ninety-nine less than regular sprite."

"Ouch." He commented. Elena huffed, "I think I am going through an existential crisis- No, I've been going through one since like years. There are moments where I feel like my existence is some sort of example for people and the type of example I am talking about is the one where you look at another person and feel like 'meh at least I am better than that.' Like I can be the face of teen pregnancy, tutorial mom and easy girlfriend all in one." She ranted. He let out a chuckle and she rolled her eyes, "This is not funny, this is supposed to be sad."

"I am sorry Miss Gilbert." He patted her shoulder lightly, "You are just degrading yourself a bit too much, you are fine, one bad date doesn't define anything."

"What do you know, you met me today. I am damn train wreck, Rachel has her pageant in two days and my best friend is not here to help her. She isn't even trying to involve me. she needs her Daddy to do her Elsa braid, design her outfit and pick out her performance. I don't even get to be a pageant mom." A tear escaped her eye. "Oh don't be so upset," he rubbed her arm. "You are just thinking about way too many things right now, there are still two days, you can show her that you can be a better 'manager' than Mr. Salvatore, At the end of the day, he is a man, he can't be pinpoint perfect about a feminine competition like you."

"But here's the thing, I am mediocrely feminine, I can't help her win." She threw up her hands in the air, "That's what you think. Of course, you can, you gave birth to fricking twins at-"

"Eighteen."

"Right. it would be a problem if you didn't care, but you do, you care about your kids." He said in a comforting tone, she nodded, "I care about them more than myself. I care about Damon too- he doesn't trust me though, I don't blame him, he shouldn't have to feel shitty about his relationship with his fiancé because of me and I did that."

"Did what?"

"I made him feel bad because I felt bad. He is happy with her because it's simple with her, he trusts her, he knows their relationship won't hurt him, but he's scared of me. it made me feel like a horrible person when he turned me down because of it, he can say I am still his best friend but I know I am not and that hurts me," she pursed her lips sitting back. "But I deserve it, I deserve more than that. I kept Rachel and Alex to myself all these years. I am a monster," she sighed.

"Don't say that," he said in a comforting tone, taking away the empty teacup from her hand. "You are a human being, we have emotions like jealousy and envy embedded in our heads and besides you didn't harm him. You want him to be happy. In the end, that's what matters, which means you aren't a bad person. You realized the mistakes you've made, that is commendable." He gave her a small smile, she felt a bit better talking about the things she had been thinking about, he looked at her in awe when she smiled back, "Oh I forgot to pay you," she said reaching for her purse. "Maybe that's why you are listening to an old lady talk."

"Oh no Mr. Salvatore did pay me." he clarified, "I didn't stay for more money, it's just you are a very polite person, I enjoyed talking to you."

"Even though I ranted half the time. That must have ruined my 'polite' impression." She chuckled, he shook his head, "No I am glad you did- you are a beautiful person, Miss Gilbert." He said in a soft voice looking at her with heart eyes. She was surprised when the hand resting on her shoulder moved to her cup her chin and he leaned forward to place a quick kiss against her lips. Her eyes widened from the quick moment and she pulled back, standing up, "Brooklyn! Oh my God, this is not appropriate," she said in a loud shriek. He freaked out, "Uh-uh I am sorry Miss Gilbert, I was- I didn't realize- I-"

"I think it's best you leave for your house." She tried to dismiss him that second blushing furiously, he nodded, "Oh yeah, I have school in the morning." She cringed at the sentence and picked up his jacket, handing it over, "GO!"

(-TVD-TVD-TVD-TVD-TVD-)

Rose looked down at her belly and then to Damon, "You shouldn't have ordered dessert, I am already bloated like hell."

"Come on Rose, it's not like we are eating like this all the time, calm down." He sat back, he had bought Rose another ring which was inside the dessert, like Elena had said it, the whole dinner was awkward, now that he thought about it. He and Elena did drive around here a lot when they were teenagers. He didn't know why he was thinking about her so much tonight, maybe because her words had offended him more, or maybe he was now cringing at his past dates. His phone rang and he picked it up, looking at the screen, 'Caroline' he shook his head, what in the world did she want to borrow at this hour, especially now that she was out of town. "Hello," he picked up the call. "Damon, oh my God!" she was laughing as if she going to die, "You are going to love this."

Damon knew that voice, Caroline had only two reasons to call him. One was when she wanted to borrow something, like a lawnmower, an extra mattress, the dryer. The second was when she had news, he preferred the latter, no matter how much she showed that he didn't care about 'drama' he always had a secret interest in knowing the nasty details of a normal boring life of another person and Caroline was one of his credible sources, these calls with her would long hours when she had details but right now he was in the middle of his date.

"Can you call later, I am with Rose." He said in a low voice so Rose wouldn't hear.

"Later is no good. It's about Elena. Did you guys have some 'who has the better date night' thing going? LOL." She chuckled loudly. He frowned, "Kind of."

"Well you fucking won!" she squealed. Damon bit his lip, he had to know this, he got up and covered the phone with his hand, "It's an important call sweetie, I'll be back in five." She shrugged, "Okay."

He immediately raced to a corner and put the phone to his ear, "What happened- give me the condensed form and we will talk in detail later."

Caroline told him about the failed date night Elena had and Damon couldn't help but half laugh and half feel sorry for her. Some details about Kai also made him laugh so much that the people around were concerned if he was a lunatic or not. "Poor Elena," he said with fake pity and sighed patting his chest to calm down his heartbeat, "I warned her not to go and make a fool out of herself. But you know what they say, you have to kiss a lot of frogs before you find your prince."

"Doesn't that explain your kiss too." She said backfiring it on him, he rolled his eyes, "I am more of a taken prince at the moment."

"Speaking of kisses." She chuckled, "You know the babysitter you guys hired- kissed her."

"What?" if he was drinking something, he'd spit it out now, "Are you serious?"

"Yeah- he was weird, Elena had a whole mental breakdown over it," Caroline said in a concerned tone, "No that's not possible, Elena's for sure lying, I mean- how in the world- that boy was like seventeen." He argued, out of words clearly, hear he was 'fearing' kai and the guy who took the cake was a snake in his own house.

"Yeah, but Elena's MILF material," Caroline said in a naughty tone. He scrunched up his face at the thought, "Thanks for the images, Caroline." He hung up and went back to his table, his dessert sitting on his side and Rose had finished hers, "Uh- wow you ate all that? "

"Yeah, um why." She asked, he down on his chair and moved his fork in his piece of cake over and over, "Maybe it's here."

"What's wrong?" she asked worriedly.

"Uh, nothing." He smiled, " Were you by any chance choking to death while eating that?" he gestured to her clear plate, she shook her head, "No, why are you saying all that?"

"Because you ate a diamond ring."

(-TVD-TVD-TVD-TVD-TVD-)

A/N: Hello friends, long time no see. I hope you are all safe and in your homes. This lockdown is very necessary and as a person who loves to enjoy long walks (And nothing more of the outside world) I am also staying in and prioritizing health. I hope you do that too. Thanks to my beta for editing this and thank you all for your kind reviews. Keep it coming, now as I am at my home. I'd be able to write more too. Again thank you for your patience with these stories. Do leave a review. Love you!