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Dating Disasters

Summary:

The Santos Senior Staff discuss disastrous dates.

Notes:

This scene has long been in my head cannon since he started having a head cannon. I hope you find it entertaining.

(See the end of the work for more notes.)

Work Text:

Since moving into the White House in January, the Santos’s had made an effort to have social evenings with their senior staffs at least once a month. This was partly an effort to maintain staff morale and make the people they depended on professionally feel appreciated, but also for their own wellbeing. Most of their previous social network were back in Texas, and it was hard making new friends when they had to be vetted by the Secret Service before you could even meet for a coffee. Therefore, Helen especially liked these evenings to be light and full of laughter. Conversations about politics were severely frowned upon.

 

This evening, the group had split between those who wanted to watch a baseball game and those that wanted to drink wine and have a gossip. Initially, Edie and Lou had joined the President, Josh, Sam and Bram to watch the game. However, Edie made a swift exit when her team began to get beat, and twenty minutes later Lou came to believe the laughter in the next room sounded more entertaining than listening to the ‘armchair coaches’ she was with giving batting advice.

 

Shortly after Lou joined the women, namely Helen, Donna, Ronna and Annabeth as well as Edie, the conversation turned to dating disasters. Helen shared her father was very strict when it came to dating, but one night when her parents were out she’d sneaked a boy over. Unfortunately for her and her date, her parents returned earlier than expected and she had to usher her date out of the kitchen window as her parents walked in the front door.

 

Edie told of one date who’d invited her to a nice restaurant, ordered the most expensive thing on the menu but when it came to paying, had ‘forgotten’ has wallet. She was most annoyed because she’d given him the benefit of the doubt, and gone on a second date, during which the guy suddenly realised his wallet had been ‘stolen.’ He didn’t get a third date.

 

Ronna’s story related to her teenage years. It was the only time she’d dated a guy, and she naively thought the relationship was going well until he complained she seemed to want to spend more time with his sister than him. That caused her to come to a lot of realisations about herself, which she’d later thanked him for, and there were no hard feelings.

 

Annabeth of course had a list, seen as she aimed to go on at least one date a week. However, all present decided that the guy who fell asleep when she was telling him about her lead role in her high school musical was probably the worst.

 

Lou said she hadn’t had any dating disasters as she would cut and run after half an hour if she wasn’t ‘getting the vibe.’ However, she admitted her flirtation with Otto ended after catching the episode of Friends where Monica dated the college student, and although her and Otto wasn’t that bad, she started seeing the college student’s face whenever she thought of Otto. No, it had to end.

 

After the laughter died down, Helen, after a sip of wine, said, “And last but not least, our enigmatic Donnatella!”

 

Donna laughed. She knew there were dating disasters she couldn’t mention, like Josh having to save her from a perjury charge when Cliff Calley had seen her diary, and those she didn’t want to mention – being manipulated into taking the blame for a quote to save a short term partner’s career didn’t paint her in the best light. However, as nobody else (apart from Lou) had named names, she felt there was one she could share, “Well, there was one night this guy I’d liked for a while had kissed me earlier that day, so I left my room key on the table, giving him the look. Unfortunately a friend thought I’d just forgotten it, grabbed it before he did, and gave it back!”

 

Everybody laughed, and luckily Ronna and Edie didn’t recognise the situation. There were choruses of “If he’s not quick enough, he doesn’t deserve you” and the conversation moved on.

 

A short time later, the game finished and the men joined the women in the lounge. Donna scrunched up on the sofa so Josh could sit beside her, but as there really wasn’t enough room, was half on his knee, the other half on the couch, and leaning against his chest. When working, they were careful to maintain a professional distance but on social nights were happy to be more tactile, although Lou warned them of physical violence if they even thought about kissing each other in front of her.

 

“There was a lot of laughter coming from in here!” commented Matt, “What were we missing?”

 

Helen grinned mischievously. “Disastrous dating stories! Actually, now that you men are here, lets get a male perspective!”

 

This led to cheers of agreement from the females in the room, whilst the men groaned. “Alcohol will be withheld unless you join in!” Helen warned.

 

“OK, I suppose I should go first.” Said Matt. He knew that although Helen found these conversations amusing, there was a deeper motive. She wanted to get to know these people better, and they all become relaxed in each other’s company. “I want to pick a date up once, and her father thought I was the guy who had cheated on her sister the month before and chased me away with an air rifle. To him, all Hispanics looked the same!”

 

Whilst the reaction to this story was frustration and disappointment at the ignorance of some people, Bram was heard to mutter “I better have a contingency plan if the guy ever sells that story to the press.”

 

Bram’s story was from his school prom, when the girl he’d spent weeks building up the courage to ask to be his date had gone home from the prom with his friend. “She only went with me to get to him.”

 

Sam’s story was obvious. “Well, I slept with a call girl!”

 

Laughter erupted as Sam launched into his defence that he didn’t know that at the time and that definitely wasn’t the arrangement they had, that it was consensual, not contractual! Lou and Edie could remember it being reported in the press at a time, jogging Helen’s memory with a “That was you!”

 

Ronna however, looked confused. “I can’t remember that at all. Mind you, I’d have only been about 15 and wasn’t quite so into politics back then, so I’d have been reading the entertainment pages, not the political scandal!”

 

That led to everybody else groaning as such a comment made them feel old, Lou throwing a cushion at her in protest!

 

“So that just leaves Josh!” grinned Helen, causing her husband’s Chief of Staff to squirm.

 

“Which one are you going to choose, you have some many!” smirked Sam.

 

“Oi! You’re meant to be my friend.” Josh shot Sam a mock dirty look as the rest of the room laughed and a comment of “I bet we could be here all night” was heard from Edie. Donna just patted his knee, imagining the story would be about having to make do with his flat instead of Tahiti from his days with Amy.

 

“OK! OK!” said Josh, quietening the room. “I don’t know why you all think I’m a bad dater, I took Donna to Hawaii for our first date!”

 

“Nine years late!” snarked Annabeth, to more laughter.

 

“Well, there was this one time the girl I’d liked for ages had indicated she might like me earlier in the day. Then on the night, she passed me her room key but before I could grab it, somebody else grabbed it and gave…”

 

The men were confused as the women in the room erupted into uncontrollable laughter. Helen almost spat her wine out and Ronna said, “That explains Donna’s story. I knew not many people would pass up that chance.”

 

Donna turned to him and hit him on the shoulder. “Out of all your dating disasters, you had to choose the same as me!”

 

“Hey,” Josh rubbed his shoulder, looking wounded, “You had your fair share of gomers and I spoilt loads of your dates. How was I to know you’d choose that one?”

 

The President asked, “When was that?”


Josh and Donna looked at each other, and a look passed between them giving mutual consent to share more of the story. “The campaign.” Admitted Donna.

 

Sam looked panicked. “Not the Bartlett campaign?”

 

“No.” said Josh, “This last one.”

 

Looking relieved, Sam said, “Thank God. Returning a forgotten key is something that I’d do and I just had an awful thought CJ was going to blame me for making us have to watch you two moon after each other for 9 years!”

 

But Ronna clapped her hand over her mouth, “It was me, wasn’t it? I picked it up and gave it to Edie!”

 

Josh grinned. “Then on the night of the election criticised me for not ‘getting onboard” when you’d sabotaged my one chance of doing so!” Everyone laughed, “Good job I like you!” he finished.

 

Later, as they were riding home, Donna looked at Josh, “The reason I chose that one? That was the one the only one that mattered!” She kissed him on the mouth. “Good job you made up for it!”

Notes:

Feedback and Kudos always welcome