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I'll Be Right Over Here: The Wingman Podcast

I'll Be Right Over Here: The Wingman Podcast

By Cleveland Comedy Network
I'll Be Right Over Here: The Wingman Podcast is hosted by comedian, author of "Memoirs of Wingman" Steve Guy and fun-loving, say-anything personality Rebecca Maxwell (owner of multiple viral TikTok videos regarding relationships, sex, and dating). Together the two talk about topics relevant to improving your love, dating and social lives and provide advice and insight from their own lives and occasional guests. Whether you're single, taken, or even married, male or female, the Wingman Podcast is here for you!
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Age Gaps in Dating & Hook-Ups
Sure, we've all seen the celebrities that date someone that we deem "arm candy" and the person is 20 or 30 years younger, but does this happen for everyone else? Is there a cutoff for an age gap? How do you handle it? Is the cutoff different if you're dating or just hooking up with someone with a larger age gap? Hosts Steve Guy (comedian/author Memoirs of a Wingman) and Rebecca Maxwell (owner clothing) discuss it all on this week's episode of I'll Be Right Over Here: the Wingman Podcast and include stories of their own dating lives with age gaps, and yes, talk about sugar daddies. Have a question or need advice? Have your own story about a topic from an episode? Email the show or reach out to one of the hosts on Twitter: @TheSteve Guy or @Rebecca__max Check out other podcasts from Cleveland Comedy Network This podcast was recorded at Golden Ox Studio in Cleveland, OH
April 14, 2021
The One, Soulmates, and Twin Flames
Things get deep on this week's episode as hosts Steve Guy (comedian/author, Memoirs of a Wingman) and Rebecca Maxwell (owner Two.One.Thrift. Clothing) dive into the discussion of whether or not soulmates truly exist. They'll try to make sense of different terms and break them down like; "The One" "Fate" "Twin Flames" and more. Do you think you've met your soulmate or anything remotely close to what's discussed in this episode? Let us know! Or hit us up for any dating/relationship advice or to share a story, by emailing us Follow Steve and Rebecca on Twitter! This episode was recorded at Golden Ox Studio and the show is part of the Cleveland Comedy Network!
April 7, 2021
Mixtapes are for Lovers
This episode throws it back old school. A shout out to those who made mixtapes on cassettes for their crushes. Burned Mix CDs. What kind of effort did it all take? Does anyone even do anything comparable anymore? Do people still get down and have soundtracks for those baby making times? Hosts Steve Guy (comedian/author Memoirs of a Wingman) and Rebecca Maxwell (owner Two.One.Thrift Clothing) reminisce and contemplate all of these answers and more, including tossing out some recommendations for a variety of situations. Do you have a dating story or looking for some dating or relationship advice? Email the show or hit up the hosts on Twitter: @thesteveguy or @rebecca__max Check out other shows from Cleveland Comedy Network!
April 1, 2021
Breaking Up Is Hard To Do - How to end things
Everyone knows that breaking up is hard to do, no matter how early or how far into dating someone we all are. It's why so many people get stuck in relationships longer than they should be and it's also why so many people do it so immaturely. On this week's episode of I'll Be Right Over Here: The Wingman Podcast, hosts Steve Guy (comedian/author Memoirs of a Wingman) and Rebecca Maxwell (owner Clothing) discuss how to go about ending things with someone in a polite and respectful manner. So forget about ghosting finally, take a listen and find a better more mature way to end something that isn't working out. You just might find that you're not the only one who doesn't think it's working! Follow the hosts on social media Want advice or have a dating story you'd like to share? Email the show;
March 24, 2021
Be Prepared - Keeping Your Home Date or Hookup Ready
Have you ever had that one night stand that you wanted to be more than a one night stand and you're not sure where it went wrong? Believe it or not, not having your home prepared to entertain a guest of any sort may have been the reason. In this episode, hosts Steve Guy (comedian/author, Memoirs of a Wingman) and Rebecca Maxwell (owner discuss how to keep your home ready for guests in a manner that shows off you're a mature adult, is inviting to bringing home a date, but isn't an obvious showing that you're just trying to get laid. What general items should you have around your house? What should the refrigerator contain? All of that and more on this episode of I'll Be Right Over Here: The Wingman Podcast. Do you have a dating story, want advice, or thoughts on the topic? Email the show at and we'll read it on air and talk about it. Check out the entire podcast lineup from Cleveland Comedy Network, a branch of Cleveland Comedy Festival.
March 10, 2021
A New Approach on How to Approach People
As the warm weather slowly starts to creep in throughout the states and the number of vaccinations also increase, people are starting to see light at the end of the tunnel and looking forward to interacting again. For some, it means venturing out for the first time since the pandemic and talking to others. What will it be like to approach someone you make eye contact with in a bar in a post pandemic world? Hosts Steve Guy (comedian, author of Memoirs of a Wingman) and Rebecca Maxwell, provide some fun ideas to help guide you into this new world of dating. Email us with questions if you're in need of advice, or have a dating story of your own, Check out other podcasts from Cleveland Comedy Network!
March 3, 2021
Deal Breakers for Dating
When it comes to dating, whether we know it or not, we all have deal breakers. Those are the traits that make us say, "This person isn't for me." On this week's episode, hosts Steve Guy (comedian, author Memoirs of a Wingman) and Rebecca Maxwell, are joined in studio by Rebecca's friend Alli to talk all about different deal breakers. Does your person need to be a certain height? Do they need certain likes or dislikes? Do political beliefs need to line up? All of that and more on this week's "I'll Be Right Over Here: The Wingman Podcast" This week's episode was recorded at Golden Ox Studio in Cleveland. For more information on audio help that Golden Ox can provide, including recording of voiceover work and radio ads, visit Check out other podcasts from Cleveland Comedy Network by visiting
February 24, 2021
Nice Guys Finish Last
"Nice guys finish last," is a phrase that's been around for decades. On this week's episode cohosts, Steve Guy (comedian, author Memoirs of a Wingman) and Rebecca Maxwell, break it all down. Do they really finish last? If they do, why do they finish last? They'll share their stories and experiences along the way and provide insight so that whether you think you are a "nice guy" or you're looking for one, you've got something to think about. Email if you want dating advice or have an interesting/horrific dating story and experience.
February 17, 2021
The Manscaping Episode
There are so many questions with regards to whether or not a man should shave his nether region and if so, how trim should he be? Even ladies have this discussion for themselves. Hosts Steve Guy (comedian, author Memoirs of a Wingman) and Rebecca Maxwell try to make sense of all of it and answer each other's questions about the difficulties of each. They also try to provide tips on general rules to adhere to when manscaping your body. Sit back, strap in, and listen to the awkward conversation of a topic you've wondered about, but never asked for an opinion on. Follow our hosts on twitter, @TheSteveGuy or @Rebecca__Max Have a dating story or need advice on dating, current relationship or anything related? Email Opening/Closing song: Big Bad Voodoo Daddy - When It Comes to Love Listen to more podcasts from Cleveland Comedy Network
February 10, 2021
Valentine's Day in a Pandemic - How to Celebrate
On this week's episode, hosts Steve Guy (comedian/author Memoirs of a Wingman) and Rebecca Maxwell, get you ready for Valentine's Day with enough time to still make plans. It's not an ordinary year for Valentine's celebrations with COVID restrictions and extra precautions being taken, so the duo takes that into consideration while helping you make the most out of it. They also share some of their worst Valentine's Day stories in their own personal dating histories. Take a listen, take in some ideas, and enjoy the day for lovers when it arrives! I'll Be Right Over Here: The Wingman Podcast is part of the Cleveland Comedy Network, a branch of Cleveland Comedy Festival. For more podcasts from the network visit 
February 3, 2021
Are you Talking, Dating, or Seeing Someone? The Labels & Levels Episode
So you're interested in someone. You're having some conversations and maybe more. Now the confusing part. Are you talking to that person? Are you just hanging out with that person? Are you dating that person? Or are you seeing that person? The labels and levels of the world of dating seem to complicate everything. On this episode, hosts, Steve Guy (comedian, author of Memoirs of a Wingman) and Rebecca Maxwell try to help you make sense of it all and describe what each term means and what the levels should consist of, so you have something to work off of as a standard. Follow our hosts on Twitter:  Purchase Steve's fun fictional book Memoirs of a Wingman at To find more podcasts from the Cleveland Comedy Network (part of Cleveland Comedy Festival) visit or follow on social media, @clecomedyfest
January 27, 2021
Bad First Dates - Stories and Advice on How to Avoid Them
Strap in and buckle up as hosts Steve Guy (comedian, author of Memoirs of a Wingman) and Rebecca Maxwell share first date horror stories and go through various rules of etiquette for successful (and respectful) first dates. All of that of course includes how to avoid the things that make a first date go bad. Drinking limits? Are you an introvert or extrovert? First date ideas, and so much more. I'll Be Right Over Here: The Wingman Podcast is produced by Cleveland Comedy Network, a division of Cleveland Comedy Festival.  For more podcasts from the network, visit
January 20, 2021
Don't Want Covid? Don't Eat Ass.... and other things - Wingman Mailbag
We opened up some emails and messages and dedicated this week's episode to those. Steve has a story about a woman who once thought she was a current NFL Quarterback's girlfriend, while in college. Some wanted Steve and Rebecca's thoughts on the CDC and other health department guidelines of sex during the pandemic. Would you wear a mask during sex?  If you want advice, have something to share, or just a queston, email 
January 13, 2021
"Hey I Remember You!" - Rekindling Childhood Crushes
EVERYONE has had a childhood crush, probably more than one. In today's day of social media, most have probably looked up some of their crushes just to see what they're up to or what they look like now. This episode is dedicated to stories of people from the past of comedian/author of Memoirs of a Wingman, Steve Guy and cohost Rebecca Maxwell. From outrageous stories of people who had crushes on them, crushes they had, all the way to advice to you if you're looking for someone you once had a crush on or have reconnected, it's an episode that anyone can relate to (well, the idea anyway, maybe not all of the stories). Do you have a fun story to share about dating? Do you want advice from our hosts? Leave us a voice message at or email
January 6, 2021
So You Want to Date a Professional Athlete?
This week's episode skews more for the ladies, but anyone can be entertained by it. No matter what, it's likely to ruffle some feathers, as Steve and Rebecca dive into the world of dating professional athletes and Rebecca's experiences with them. They'll talk about how to start talking to an athlete and meet up, which sports are better if you're someone who wants to settle down, and of course those terms like "jersey chasers" "punk bunnies" (for you Canadians out there) and "slump busters." Want advice from the hosts or have a dating story you feel you need shared? Leave us a voice message on the homepage or email and we'll answer it on the show (we'll leave you anonymous of course).
December 30, 2020
The Holiday Dating Guide
On this week's episode hosts Steve Guy (comedian, author "Memoirs of a Wingman) and Rebecca Maxwell talk about and dish out advice on dating during the holidays. How long should you be dating when exchanging gifts? Are there levels to how many gifts or how much you spend on them? How do have the gift giving conversation if its a new relationship and you aren't even sure where it's going. When is it too soon or the right time to bring them around the family during the holidays? All of that and more on this week's "I'll Be Right Over Here: The Wingman Podcast" Do you want some advice on your love life? Send us an audio message on our Anchor page, or email and we'll answer it for you in an upcoming episode!
December 23, 2020
If You're Coughin, You're Not Cuffin - Dating in the Pandemic
Hosts Steve Guy and Rebecca Maxwell join together to talk about the variations of dating during the current pandemic and how to handle things. For those in a relationship, for those who are single, whether your heart desires something serious or something simple, during this pandemic, these two utilize their experiences, observations and knowledge to help you navigate it all.
December 16, 2020
Debut of I'll Be Right Over Here: The Wingman Podcast (hosts Steve Guy & Rebecca Maxwell)
Same Wingman podcast (sorta), NEW Name, New Co-Host! Comedian and author of the book "Memoirs of a Wingman" Steve Guy is joined by co-host Rebecca Maxwell (inspiration for BuzzFeed article due to viral TikTok). Together they talk about different topics relevant to the world of dating, relationships, and so everything in between (Sorry Moms!). Steve returns and continues what was started with the original show and its previous episodes, but this is the DEBUT for Rebecca! Listen as they reintroduce you to the show itself and a bit into Rebecca's background and world. I'll Be Right Over Here is produced by and a part of Cleveland Comedy Network, a branch of Cleveland Comedy Festival.  Visit to check out other podcasts on the Network! Follow Steve Guy & Rebecca Maxwell on social media! & & TikTok: RebeccaMaxwell69 & TheSteveGuy
December 9, 2020
Wingcast 24: Ex Lovers and Friends
Joined by returning guest, Josey, and the two discuss the pros and cons of maintaining different levels of friendship with exes. #wingman #wingmantips #datingadvice #datingtips #relationshipgoals #exes #ex #exlover
June 2, 2018
Wingcast 23: Safety Net
Welcome to Season 2 of the Wingcast! This week's topic is a result of an update from a listener's previous email in Season 1\. Learn what it means to be or have a #safetynet PLUS an update on a previous guest. #wingman #dating #datingtips #datingadvice #relationshipgoals #wingmantips
May 17, 2018
Wingcast 22: Dating and Insecurities
This week, the Wingman leads off the show with advice shared from a listener that emailed. The rest of the show he's joined by his friend and they discuss dating and the insecurities that come with it, especially from someone who has insecurities in general. #wingman #datingadvice #wingmantips #datinginsecurities #insecurities #relationshipgoals
February 9, 2018
Wingcast 21: Wingman to my Dad
On this episode, to celebrate his Dad's birthday, the Wingman sits down with his old man and they talk about the days when the father used his young son as his wingman after getting divorced. #wingman #datingadvice #datingafterdivorce #relationshipgoals #fatherandson
January 30, 2018
Wingcast 20: #NewYearNewMe - with guest, health & fitness guru Karissa
It's a new year and whether you're continuing something you began last year and perhaps struggling with it, or starting the new year by challenging your health and fitness this episode is dedicated to helping you. The Wingman is joined by his health & fitness guru friend, Karissa, and they discuss easy ways to improve upon these things, as well as how it can impact you from a dating standpoint. #wingman #datingadvice #healthandfitness #fitness #wingmantips #newyearnewme #newyearnewyou
January 12, 2018
Wingcast 19: Wingman and Marriage (guest Chris Clem)
On this episode, Steve is joined by one of his best friends, comedian Chris Clem. They talk about what it's like for Chris to be a wingman and be married and also how having friends being a wingman to his relationship doesn't stop just because he's married. #relationshipgoals #datingadvice #wingman #officialwingman #marriage
December 8, 2017
Wingcast 18: Where Do You See This Going?
The Wingman sits down and answers questions that he's received from listeners and friends covering a variety of topics. Would you believe people create fake Tinder accounts to catfish the person they're dating? It happens. That and so much more in this episode! #dating #relationships #wingman #datingadvice #relationshipgoals #tinder #catfish
November 30, 2017
Wingcast 17: The Art of Sliding into DMs
This week the Wingman is once again joined by his friend, Lex the Hottie Bartender. Together they discuss the proper way to go about sliding into someone’s DMs and laugh a bit about the DM slides she’s received. #wingman #datingadvice #slidingintodms #itgoesdowninthedm #officialwingman #dating #relationships
November 16, 2017
Wingcast 16: Hey, I like your curly hair
On this episode, the Wingman breaks down some things he's learned from his own dating life and shares them with you. Toss him some other hot topic social issue as well briefly and you've got an episode! #Wingman #datingadvice #datingfails #relationships
November 10, 2017
Wingcast 15: Days of Wingmen Past - Guest Rodescu Hopkins
The Wingman reminisces of times with one of his best friends, comedian Rodescu Hopkins and they reflect back on younger days and their attempts to wingman each other. Not to mention random stories of their friendship overall, sure to make you laugh. #wingman #officialwingman #datingadvice
November 3, 2017
Wingcast 14: Dating After Divorce - with guest Jess Faulstich
Comedienne Jess Faulstich returns as she and the Wingman discuss dating after a divorce. Including, getting back into it and how to approach someone just coming out of one, as well as advice for those thinking about getting married. #dating #divorce #datingafterdivorce #relationships #wingman #officialwingman
October 20, 2017
Wingcast 13: Juanda, The Penis Promoter
Standup Comedienne, Juanda Mayfield joins the Wingman to reflect back on her moments of being a "Wingperson" including the time she helped him. Not to mention the tale of her being a self proclaimed Penis Promoter for a friend. All of that, plus her struggles in being set up by other friends. #wingman #wingperson #penispromoter #datingtips #dating #relationshipgoals #officialwingman
October 12, 2017
Wingcast 12: I Think That Bartender Is Into Me (Nope, She Isn't)
The Wingman is joined by a special guest that just happens to be an attractive bartender. Lex helps settle the theories once and for all on whether or not that hot bartender is really flirting with you or just doing her job and earning a tip. #datingtips #relationshipgoals #officialwingman #hotbartender
October 5, 2017
Wingcast 11: Wingmen to a Gay Woman - guests Jayson Cross & Whitney Chitwood
Perhaps the most quotable episode yet featuring terms like "qwoke" "kamikaze semen" "f*%@ shower" and "DW" Sit back and enjoy the tale of how comedians Steve Guy and Jayson Cross played legendary wingmen (according to themselves) to comedienne Whitney Chitwood for a night.
September 28, 2017
Wingcast 10: House Party
It happens, the Summer turns into the Fall, but it doesn't mean socializing needs to end. Still haven't found that cuffing mate? Tune in and find out one method of meeting or sparking a relationship with someone by hosting your own social gathering right at home. #HouseParty #Wingman #Dating #RelationshipGoals
September 21, 2017
Wingcast 9: Dating Diversity Training with guest Sonal Aggarwal
Wingman, Steve Guy, is joined by standup comedienne, Sonal Aggarwal, from Chicago. Together they talk all about Sonal's dating life while dating in different cultures. Toss in her stories about cockblocking and lessons learned from being a terrible wingwoman, and it all makes for a fun time! #wingman #wingcast #dating #relationships #diversity
September 14, 2017
Wingcast 8: What the F*@% is Cuffing Season?
Ah yes, #CuffingSeason is upon us and perhaps you're asking, what is that? This week's episode is all about what it is, why it is, and how to figure out if you're being cuffed! #Wingman #OfficialWingman #DatingAdvice #RelationshipGoals #Wingcast #Dating #Relationships #Cuffing
September 7, 2017
Wingast 7: A Girl and Her Open Relationship
This week, the Wingman is joined by friend and fellow comedian, Jess ( @epicfaul on social media ). They discuss her open relationship, what that means and what it entails. Along with what one should expect trying to date someone or a couple in an open relationship. #wingman #wingcast #openrelationship #dating #relationshipgoals
August 31, 2017
Wingcast 6: What's Your Number? (The Sex One)
Ever had the number talk? Thinking about? Tune in to listen all about the possibilities that could come from asking your partner how many people he/she has slept with. #wingman #sexnumber #numbertalk #wingcast #dating #relationships
August 24, 2017
Wingcast 5: Country Concert Women Are The Hottest
On this episode; the two different types of friends that ask you to game plan wingman scenarios for the evening and where do you go if you actually want to see the largest gathering of attractive women in your area? The answer is in the title. #wingman #wingcast #officialwingman #dating #advice #relationships #country
August 17, 2017
Wingcast 4: Please Excuse My Cheating, It's Because I'm Pretty
The Wingman rants about a piece written for the DailyMail in the UK by a woman who claims that due to her being pretty it caused her to cheat. #Wingman #Wingcast #Dating #Relationships #TooPretty #Cheaters
August 10, 2017
Wingcast 3: Trust & Social Media
It's 2017, almost everyone is on Social Media of some sort at this point. How much is too much in checking up on the person you're dating through social media? This episode is all about your relationship and how it relates to social media. #Wingcast #Wingman #socialmediatrust #wingmantips #officialwingman
August 3, 2017
Wingcast 2: Just Communicate, People!
Communication is the key to a successful relationship of any form. Let the Wingman break it down for you in this episode. #wingcast #wingman #officialwingman #communication
July 27, 2017
Wingcast 1: Finding Your "Type"
Keep searching for someone that's your "type" and it just doesn't seem to be working out? The Wingman explains why you're doing it all wrong. #wingcast #officialwingman #wingman #datingtypes
July 20, 2017