Coming Out On Top Wiki

Philbert "Phil" Healy is a potential love interest of Mark and cousin of Penny in Coming Out On Top.

Character Summary[]

Phil is a marine fresh out of boot camp and is being considered for Recon program once he graduates from infantry school. He is very disciplined and strict, but has a hotheaded streak that sometimes crops up.

During his childhood, Phil was rather nerdy and played a lot of Dungeons & Dragons. He also developed a fondness for obscure trivia through his father's collection of military history books. Although he considers most of his former activities trivial and wasteful after boot camp, he still holds a distinct fondness for trivia. Phil even gets aroused by Mark's ability to answer trivia questions correctly.

His father, Donald is running for state senate.


Phil has cropped hair with a slim muscular build and medium dark skin. His body is described as being solid as a statue, attributed to his boot camp training regimen. He often wears a brown vest and white shirt with a black tie. On causal occasions he wears a red polo tee, or a short sleeved black tee. And a huge meaty cock.


Penny mentions her cousin Phil as soon as Mark comes out to her and Ian. She immediately gets the idea of setting the boys up.

Eventually Penny gets the idea of all three of them having lunch together the day Phil comes from boot camp, to which Mark reluctantly agrees. However when the day comes Penny finds herself busy and asks Mark to pick her cousin at the airport for her. The meeting between Mark and Phil does not goes smoothly, Mark puts his foot in his mouth several times and Phil acts cold and dismissive.

Later Penny asks Mark to accompany her to her uncle's (Phil's father) fundraiser party. Mark agrees, despite not liking the idea of meeting Phil again. Before the event, Mark confesses his nervousness to Ian and he gives Mark advice on how to impress the "rich and powerful" along with lending Mark his top hat for him to wear.

At the party Mark meets Donald and his aide Patrick. He bumps into Phil who disapproves of his choice of wear. They are interrupted by Mr. and Ms. Walker a couple of key donors to Donald's campaign who Mark's manages to impress by following Ian's advice. The Walkers then introduce the boys to their daughter Violet.

Later, Phil asks Mark to accompany him and Violet to a ballet concert because the Walkers were impressed by him and Phil has to court them to help his father's campaign. Mark accepts. While on the way to the ballet, Violet makes Phil change course to a night club. She leaves the car and runs into the club, forcing the boys to go after her. Mark finds Violet and while he is talking to her he's interrupted by Knutson and Zelinski, two of Phil's colleagues from boot camp. Phil joins them and Knutson and Zelinski tease him for being in a club during his leave. Phil's dismisses them and asks Violet to come back to the car. Violet defers to Mark, but he defends Phil's actions which makes Violet cry. With the mood killed, no one goes to the ballet and Phil drops Violet at home instead. On the way to Mark's apartment a clearly warmer Phil asks for Mark to help him train for a swimming test, which Mark accepts.

Mark and Phil go to the beach to compete against each other in a swimming competition. If the player decided to take short, intense breaths and/or lifting your head as high as possible, Mark will be swept away by a current, leading Phil to come to his rescue. Afterwards, they go to a sports bar and have fun until they bump into Knutson and Zelinski again. The two harass Phil for being gay, but Mark cools the situation down before it turned physical. The boys return to the car where Phil vents his frustrations and Mark offers his support for him, possibly in the form of a blowjob. Afterwards Phil drops Mark home.

Later, Phil calls Mark to tell he's going out with Violet again because the Walkers insisted and the only way they would be able to see each other that week would be if Mark tagged along, which Mark does. Eventually they go to the same sports bar they went the previous week. The boys enter a trivia contest at the bar, in which Phil gets eliminated and Mark must win three rounds of trivia to win. If the player is successful in the contest, Mark earns 150 dollars from the cash prize he split with Phil. When the night is over, Phil drops Mark off at his dorm and they have sex. Ian would walk in on them, regardless of the player's choice to dominate or submit during sex.

Mark attends a fundraiser thrown by the Walkers to see Phil again. If the player refused to take the top hat off at the first fundraiser party, Patrick will pull Mark aside to talk to him about it. Phil later shows up at Mark's graduation party to bid him farewell before he leaves and asks him if he'll miss him. The boys exchange a romantic moment before the game ends and Mark graduates as Phil left for Recon. After Phil leaves, he and Mark begin dating long distance. They break up at some point for 12 hours, 34 minutes, and 4 seconds before getting back together again. When Phil comes back, Mark is there to greet him at the airport.


I'm gay. (Proceed to #2)
I'm gay. High five! (Proceed to #2)
Uh, just a reminder. (Just pick one of the other for the sake of simplicity)
All right. (Starts Alex's route, which can later be stopped, but for the sake of simplicity pick the other.)
Eh. (Proceed to #3)
Fine, fine! (Starts Alex's route, which can later be stopped, but for the sake of simplicity pick the other.)
No. (Proceed to #4)
I bet it's nice... (Proceed to #5)
I wonder what your... (Proceed to #5)
I've got a lot on my mind... (Proceed to #5, recommended)
Borrow his lube. (Just pick the other for the sake of simplicity)
Ew, are you kidding me? (Proceed to #6)
Whack off. (Just pick the other for the sake of simplicity)
Sleep like an angel. (Proceed to #7, recommended)
HELLLOOO Professor. (Just pick the other for the sake of simplicity)
Meh. (Proceed to #8, recommended)
Penny! Enough with the orange photos! (Proceed to #9)
Please, can we beta test another time? (Proceed to #9)
NO. (Proceed to #10)
Okay, okay, OKAY!!! (Proceed to #10, highly recommended)
Sure, no prob. (Starts Ian's route, which can later be stopped, but for the sake of simplicity pick the other.)
No. (Proceed to #11)
I'm biding my time. (Proceed to #12)
I'm planning to tell them.  (Proceed to #12, recommended)
Tell them. (Proceed to #13, recommended)
Oh, you know. (Proceed to #13)
Tutor at the Student Learning Center for extra cash. (Proceed to #14)
Get a head start start on term paper. (Proceed to #14)
Watch the Horror Movie... (Proceed to #14)
Beat off... (Proceed to #15)
Study... (Proceed to #15, recommended)
Can you guys handle this? (Proceed to #16)
One of us should go... (Starts Jed's route, which can later be stopped, but for the sake of simplicity pick the other.)
God, FINE! (Proceed to #17, necessary for a successful romance)
You know who loves getting up... (Locks you out of Phil's route)
You and Penny are pretty close, huh? (Proceed to #18, recommended)
So I hear D&D was a... (Proceed to #18)
Tell me more about... (Proceed to #18)
Eat breed. (Proceed to #18)
Accept the job. (Starts Brad's route, which can later be stopped, but for the sake of simplicity pick the other.)
Tell her no. (Proceed to #19)
All right, all right. (Proceed to #21, recommended)
Are you done with armchair psychologizing? (Proceed to #20)
No thanks. (Proceed to #22)
GAWD, FINE! (Proceed to #21)
A couple laps at the pool sound refreshing. (Proceed to #22)
Work up a sweat on the treadmill. (Proceed to #22)
Exercise? (Proceed to #22)
Tutor at the Student Learning Center... (Proceed to #23)
Get some extra studying done. (Proceed to #23)
Accompany Ian and Penny to... (Proceed to #23)
Fine, fine... (Proceed to #24)
I'm not interested... (Proceed to #24)
All right, I'll go... (Proceed to #25)
Sure, it sounds interesting. (Proceed to #25)
No, I've got better stuff... (Ends route)
Like what? (Proceed to #26)
That's idiotic Ian. (Proceed to #26)
Keep the hat on for now. (If you wear that hat, you will have a "negotiation" with Patrick at #62. Proceed to #27)
Take the hat off. (Proceed to #27)
Badminton. (Proceed to #27, necessary for a successful romance)
Racquetball. (Proceed to #28)
Swimming. (Proceed to #28)
Wealthy as I am... (Proceed to #29)
The emperor is rich... (Proceed to #29, necessary for a successful romance)
Wealth consists not in having... (Proceed to #29)
Fine, fine. (Proceed to #30)
Not gonna happen. (Proceed to #31)
You're here for a purpose...  (Proceed to #31)
Maybe see...  (Proceed to #31)
Hit the treadmill. (Proceed to #31)
Tutor at the Student Learning Center... (Proceed to #32)
Get some extra studying done. (Proceed to #32)
Invite Ian and Penny to the beach... (Proceed to #32)
You know what? (Proceed to #33)
No. (Ends Route)
Sorry. (Ends Route)
Hey, take a deep breath... (Proceed to #34, recommended)
Look on the bright side. (Proceed to #34)
Looks like we got a... (Proceed to #34)
Okay. (Proceed to #35)
I have a better idea. (Proceed to #35)
Violet, Phil's just trying... (Proceed to #36)
C'mon y'all... (Ends Route)
Maybe I just want to help out Penny's uncle. (Proceed to #37)
Maybe I think you're cute. (Proceed to #37, recommended)
It's about freaking time you thanked me. (Ends Route)
You're on. (Proceed to #38)
No thanks,... (Ends Route)
Tutor at the Student Learning Center... (Proceed to #39)
Get some studying done. (Proceed to #39)
Invite Ian and Penny to... (Proceed to #39)
Sounds fun, I'll be there. (Proceed to #40)
Sorry, I've got... (Ends Route)
It certainly couldn't hurt, could it? (Proceed to #40)
No, just no. (Proceed to #40, recommended)
Take short, intense breaths... (Proceed to #42, unlocks #43)
Take slow, methodical breaths. (Proceed to #42, recommended)
Lift your head higher than normal. (Proceed to #43)
Lift your head just high enough. (Proceed to #45, recommended, if chosen the second option before unlocks CG#1)
It would serve you right. (Proceed to #44)
SIR, YES SIR. (Proceed to #45)
Oh shut it. (Game Over)
SIR, YES SIR. (Proceed to #45)
Well, duh. (Game Over)
Do you have to yell? (Game Over)
Tutor at the Student Learning Center... (Proceed to #46)
Get some studying done. (Proceed to #46)
Since you promised the old lady... (Proceed to #46)
Sure, sounds awesome. (Proceed to #47)
Actually, you could slide... (Ends Route)
No thanks, I'm not feeling it. (Ends Route)
Not at all. (Proceed to #48)
Why don't you shut..? (Game Over)
Let Phil handle this. (Proceed to #48)
Phil, you've got more... (Proceed to #49)
Yeah, shut your... (Game Over)
Kiss him. (Proceed to #50, path to unlock CG#2)
Be sympathetic.(Proceed to #52)
Sure, I'm glad for that. (Proceed to #52, necessary for a successful romance)
Offer a blowjob. (Proceed to #51, path to unlock CG#2 and CG#3, there will be no CG#8 and CG#9 in the Ending)
I'm soooo hungry... (Ends Route, Unlocks CG#3)
It'll help you blow off some steam. (Proceed to #52, Unlocks CG#2)
Sorry. (Proceed to #52)
Tutor at the Student Learning Center... (Proceed to #53)
Get some studying done. (Proceed to #53)
Treat Penny to a dinner... (Proceed to #53)
If that's the only... (Proceed to #54)
I dunno, am I insane? (Proceed to #54)
Well, good luck. (Ends Route)
I agree, you should have your fun. (Proceed to #55)
In all honesty, you seem... (Proceed to #55, recommended)
Hell yeah! (Proceed to #56, recommended)
I dunno, man. (Proceed to #56)
#56 - Quiz
You need to win the Quiz to unlock a third of Phil's CGs. To win the Quiz easily use the roll back function (press Page Up) each time you get a question wrong so you can re-answer it. There are four alternatives to each question, so eventually you'll get it right.
But was it hotter than Death Valley on July 10, 1913? (Proceed to #58, Unlocks CG#4)
Hahaha. (Ends Route)
Grind your ass against his dick. (Proceed to #59, Unlocks CG#6 and CG#7)
Flip him over and wrestle for top. (Proceed to #59, Unlocks CG#5)
Tutor at the Student Learning Center... (Proceed to #60)
Get some studying done. (Proceed to #60)
Accompany Ian... (Proceed to #60)
I'd love to. (Proceed to #63, recommended)
Can't we do something else, just the two of us? (Proceed to #61)
It's finals week and I'm REALLY... (Ends Route)
Okay, I'll be there. (Proceed to #62)
Sorry, but no. (Ends Route)
You're asking me to hide the fact that Phil and I are going out? (Proceed to #63)
If it helps his father's campaign,... (Proceed to #63 Recommended)
Only one question, Pat. (Ends Route)
Don't, Phil. (Romance Successful, unlocks CG#8, CG#9 if you didn't offer him a blowjob or offered him but then Removed your hand)
Hit Knutson. (Ends Route)
Let Phil handle it. (Ends Route)



Phil was not impressed by Mark at first due to Mark putting his foot in his mouth a few times in their first meeting and Phil's own disconnect with civilian life. Phil starts to warm up to Mark after Mark helps him deal with Violet's antics on the night they were supposed to go to a ballet concert. Their relationship grows stronger afterwards with Mark helping Phil train for the swimming part of his Recon test, and the boys competing on a trivia contest together. After Phil is deployed to recon they get in a long distance relationship. Notably, Mark helps Phil keep his calm at various points during his route, especially when dealing with Violet and Knutson and Zelinski.


Penny and Phil were very close growing up. Phil recalls fondly one instance in which they accidentally burnt his parent's garage when they poured water on the sodium fire they'd created. Even after his time in boot camp, their relationship is still strong. Phil tries to get Penny to stop calling him "Philbert", as he believed he had outgrown the name, but relents by the game's end, admitting that he missed hearing it from her.


Violet is the daughter of his family friend, the Walkers, who are also large donors to his father's campaign. Phil resents that he has to entertain Violet for the sake of his father's campaign and finds it very difficult to put up with her, but he acknowledges that she is a not a bad kid.

Knutson & Zelinski[]

Phil's colleagues from boot camp. The pair constantly tease and harass Phil in order to get a reaction out of him. Most notably, they try to insinuate that Phil is gay with statements about how he admired his comrades in boot camp.


  • Phil was the president of the chess club and plays the bassoon.
  • He is the middle child of the family, with an older sister in business school and a younger brother still in high school.
  • His mother is a former ballerina, currently having a debilitating illness that keeps her mostly at home.