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Chapter 59
by
Jjaymes94
What's next?
Double date
Dean, Brooke, Richard and Alexa all get into Dean’s car to go to the restaurant. Dean drives with Brooke on the front seat, Alexa and Richard in the back together. It’s a short drive to the restaurant, the songs on the radio fill the silence in the car.
They arrive at the steakhouse and head in, they had a reservation and we’re able to walk right in to their table. They sit at a high top bar table, Dean and Brooke sit on one side together and Richard and Alexa sit on the other side with Alexa sitting directly across from Dean and Brooke across from Richard.
They all look over the menus, no one wanting to talk first it seems. Brooke finally breaks the silence and starts to talk about the restaurant. Dean and Brooke have been there before so they were familiar with the menu, so they talked about what they liked and didn’t like. Brooke seemed to be the only one talking going on and on. Dean decides to butt in, if Richard and Alexa were to get to know each other they needed to share personal information with one another.
Dean gets the ball rolling, “Alexa, so what do you do for a living?” Everyone’s attention moves to her. “Well... I’m a photographer.” She says. Brooke chimes in, “She takes amazing photos!” She directed that comment towards Richard. He continues to look down at his menu and shake his head acknowledging them but not saying anything. Alexa sees that he is nervous about the date and tries to help him out, “So Richard, what do you do?” Dean doesn’t think this is a good question considering he’s a deadbeat. Richard was about to speak but then the waitress came to the table.
Dean decides it would be best to get a round of shots and to hopefully get everyone past the awkwardness he and everyone else must feel. The waitress leaves them. Dean doesn’t forget about the lingering job question that Richard didn’t answer but doesn’t want to bring it up because it would make Richard appear less attractive to Alexa if that’s possible. To Dean’s surprise, Brooke speaks up, “So Richard, you were telling Alexa about your job?” Dean’s eyebrows raise interested in hearing Richard’s answer. Alexa intently listens as well.
Richard starts to stutter and mumble, “...I I play video games.” Alexa was confused... “Video games?” She said. “Yea.” He replied. Alexa somewhat curious now, “Do you get paid?” This is painful to watch for Dean, luckily the waitress comes back with their shots and drinks. Everyone downs their drink, hopefully it relaxes everyone and gives Richard some liquid courage.
This time no one has to probe Richard into answering the question. He speaks more loudly and less nervous, “yeah, I get paid a bit to play video games, like people watch me play but I do some work for a tech company too.” This was news to Dean but apparently not news to Brooke who smiled on as Richard shared more about what he does.
“That’s nice that you get to work from home.” Alexa says, “I always have to travel for photo shoots.”
Dean still can’t get over that Richard has a job, since when? Dean isn’t sure if that’s a lie or not and is it a sustainable career? If Richard indeed has a job, that would be one of the last three things that need to be completed for Dean’s master plan to be complete. The other two items would be Richard moving out and getting his own girlfriend. Dean hopes this date will get better fast so another item can be checked off the list.
The waitress comes back and the group puts in their orders, Alexa gets another drink, apparently she downed hers already, not a good sign for the date.
Brooke and Alexa do most of the talking since they are good friends, Dean chimes in every so often. Richard still seeming nervous doesn’t add anything to the conversation and doesn’t talk unless directly spoken to. Brooke tries to include him in the conversation and talk him up a bit to Alexa who doesn’t seemed very interested in him, she only seems interested in the drinks at this point.
The waitress comes back to reassure them that the food will be out shortly. Alexa gets another drink. Richard excuses himself to go to the bathroom. Brooke whispers to Dean, “I’m gonna go talk to Richard, he’s super nervous.” Brooke gives Dean a kiss on the cheek leaving behind her bright red lipstick. Brooke excuses herself saying she’s going to the bathroom as well.
Dean turns towards Alexa as they are the only ones left at the table. Alexa sipping on her drink takes a second to point out that Dean has lipstick on his cheek. He wipes it off with a napkin. Dean decides to make small talk with Alexa. Then he becomes more forward, “So what do you think of Richard?” Dean asks. “And be honest, it’s okay.” Clearly tipsy from her numerous drinks, Alexa answers, “Well... I’m sorry, I don’t want to be mean but your roommate just isn’t my type.” Alexa was clearly a nice person, she didn’t want to offend Richard, she was being polite as possible. Dean replies, “No I get it, some people are just not compatible.”
Richard and Brooke are still gone when the food arrives. To be polite Alexa and Dean wait for them to come back. Some more times passes and Alexa convinces Dean they should eat because their food is hot. Dean agrees, they eat and chit chat. Alexa is on another drink. Dean finds Alexa to be goofy and they seem to be getting along quite well.
Finally Richard and Brooke arrive back at the table at the same time. They don’t give an excuse for being away. Brooke says the food looks good. Dean can’t help but notice the bright red lipstick she was wearing is gone from her mouth. Richard was more talkative and wasn’t staring down unless eating his food. It looks like their talk or whatever they did helped with Richard’s confidence, he didn’t seem nervous at all now.
The food was good so there wasn’t much of a conversation happening. Soon everyone was done and started to chat. Richard took more of an initiative to talk to Alexa to get to know her, Brooke would chime in to help the conversation as well. Richard started to talk about himself a little too much, trying to brag about things that Alexa had no interest in. Dean wasn’t sure which part of the date was worse, shy Richard or this Richard.
Alexa just kept sipping her drinks away, **** was the most entertaining thing to her on this double date. She seemed to be having fun, giggling with Brooke talking about other things not involving Richard. Whenever Richard spoke she would just politely nod. It had to be clear to Richard that Alexa wasn’t interested, it was clear to Dean and possibly clear to Brooke but she kept trying, probably trying too hard. Richard didn’t give up hope yet though.
The waitress came a final time with the check, Dean reached for the check but Richard snatched it away, “I got this.” He cockily said. This was a last stitch effort to impress Alexa by paying the bill for everyone. She couldn’t care less, Richard got the hint. He still forked out the cash to pay for everyone, Alexa said thanks but it clearly wasn’t the reaction Richard wanted, he got knocked down a few pegs.
The group all left the table. Alexa was clearly drunk, stumbled out of the high bar chair into Dean’s arms, she lost her balance. Dean trying to catch her accidentally gropes her. Alexa only says “Thanks for catching me!” Alexa clearly needs help walking out the restaurant, she hangs on Deans arm and Brooke helps Alexa on her other side, Richard awkwardly walks behind the three of them.
Dean and Brooke put a drunk Alexa in the backseat and Brooke joins her, Richard silently takes a seat in the front.
The four drive home after an interesting double date.
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A story about being a generous roommate
Dean and Brooke have been dating for quite some time now, completely comfortable together. They love to experiment in the bedroom and try anything. Richard is Dean’s nerdy roommate, they have know each other most of their lives with their parents being friends and neighbors. Dean feels bad for Richard because he has had no luck with the ladies. A virgin nerd who use to live in his parents basement until Dean was convinced by his own parents to have Richard move in with him. Dean figures he could help Richard out once more and share Brooke with him and tap into another sexual fetish of his... win-win? Right?
Updated on Jan 28, 2026
by Jjaymes94
Created on Sep 12, 2020
by Jjaymes94
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