Pillow Talk with Tim Young

16 Feb


I’m excited to bring you my second “Pillow Talk!”  This week, I’m talking with a talented, local stand-up comic, writer and political pundit, Tim Young.  Tim has something to say about everything.  His Twitter is @Timrunshismouth and that generally holds true.  He’s made a name for himself, not only on stage, but through the multiple publications and TV shows he’s appeared on.  He’s also known for LiveTweeting some of the worst dates that he has witnessed in public.



Tim Young



Rita:  You were supposed to be one of my 35 dates, but you bailed.  What’s up with that?

Tim:  I regret that decision every day of my life.  I look at your photo each morning while I drink my coffee and think “Tim – what did you do?!”  Then, at night, when I cuddle with your photo close to my heart, I cry myself to sleep knowing that I missed my opportunity to have you next to me.

Fine, he didn’t say that.  Here was his real answer:  I was supposed to be your 9/11 date.  Isn’t that a good enough excuse?  It was 9/11.  You can’t question 9/11!


Rita:  Don’t tell me what I can question, Tim.  So, many people know you for your stand-up comedy.  What comedians, and people, inspire you?

TimTons. I love Patton Oswald, Andy Kaufman, Bob Hope, Bill Cosby, Jerry Seinfeld, and David Letterman just to name a few.  Each of these comedians have a completely different style and each of them were the top of their game.

I’m also inspired by people who drop everything and take the risk to pursue their passion. It’s the most difficult thing anyone can do, you know, going against societal pressures to sit in a 9 to 5 all day long and do whatever everyone else is doing.  So when you step out of that box, you’re on your own and you may be the only person who believes that what you are doing is right.  So those people really are some of the bravest in the world.


Rita:  Would you say that your view on women is the same as your take on comedians….equally appealing so long as they have their own style, are at the top of their game, and take risks? Or do you tend to default towards one type of woman, style, game?

TimI definitely don’t have one type of woman, so I guess yeah, I have the same view on women as comedians, who you can’t really compare to one another as such because each has their own style.  Some suck though.  A lot of them suck.


Rita:  What advice do you have for those trying to get into stand-up comedy?

TimDon’t.  It’s an insane business to get into.  You don’t make money for a long time.  A long time.  First, you have to learn how to sort through some real dirt-bags and low-lifes in order to get 5 minutes of stage time.  You start off on shows where you sit through 15 other stand up comics who may or may not be funny and may or may not steal the jokes that you took hours to write.  Oh and you have to be nice to everyone because you never know where anyone could end up.  If you’re lucky enough to have promoted yourself properly, which takes up all your time, you might land a 10-15 minute gig that pays you $20 where you are expected to have 10 of your friends come see you.  Getting to that gig will also cost you roughly $30 in gas.  And by the time you wake up and realize you have been working your butt off for 3-4 years at comedy, you will have lost at least 1 or 2 girlfriends and half of your “friends” will have turned on you because you “just wont grow up,” and have a regular job and family just like them.

Wait.. sorry I blacked out there for a second… What I meant to say was, try your best and believe in yourself.

Rita:  Haha, the way you talk about being a stand up sounds a lot like MY dating life. Sort through dirt bags and low lifes to get 5 minutes of time with someone…having to be nice, and promote myselfproperly just to get a 10-15 minute gig that ends and I have to start all over again!! Why do you think it is that so many people in this area claim to have such an impossible time dating. Do you think it’s DC specific?

TimWell, women outnumber straight men in DC so that is an issue right out the gate.  I don’t think people want to, or are that aggressive with one another after a long day at work….they want something to be handed to them.  That just doesn’t happen, so it’s easy to write off dating as impossible rather than put in extra effort to be aggressive and find someone you match with!


Rita:  I’ve heard that you are currently out there looking for a lady friend…how’s that going?

TimIt’s going.  A lot of the women I meet in DC are either too easy, yes I said that, or too jaded by dating.  I can’t seem to find that middle ground.  I get scared off by women who are too sexually forward on a first date.  I think I lose a man-card for saying that right?  I have the same belief with groupies as I do with women who put it out there so easily.  If you are going to do that with me, you’ll probably do that with anyone.  So that’s a deal-breaker for me.

I also don’t like women who hate the concept of getting to know someone or that view me as a comic all the time.  On stage or whatever I’m a character.  Granted it’s similar to my actual self, but I don’t try to be funny when I’m not performing. Some women don’t get that.



Rita:  How is it that women aren’t getting to know someone?  What are the not doing?  What should they be doing?

TimWomen assume things about me and I assume then that applies to other guys they go on dates with. Take time to learn a person.  With me, they assume I want to be funny all the time because I’m a comic.  I don’t.  You don’t go on a date with an accountant and ask them to do your taxes at the table…  Women should come in with a blank slate and give and take to learn and share with the person they’re out with.

 Rita:  And the DC ladies are either easy or jaded?

 TimWomen either want to have sex right away or hate dating and that comes off immediately.


 Rita:  What qualities do you look for in your potential partner?

 TimThere are the cliché things like smart, funny, attractive…but I really need a woman who is tolerant of me.  Whether it be when I need to write something or be on the road, or the fact that I do love childish things like video games, cool action figures, etc.  I don’t pretend to be someone I’m not and I need someone who likes me for who I am.

I also like a woman who is confident in herself and not jealous.  I interact with a lot of women all the time, so she needs to know that I won’t run around on her.  She also needs to be able to tell me when I’m wrong, when I’m wrong.  I like directness and someone who stands up for herself if I do something stupid…which I probably will do at some point in a relationship.


  Rita: When you describe your perfect partner, it kind of sounds…selfish Tim.  A woman to give you everything that you want….to let you do everything you want…..I don’t really hear you talking about what you can give a woman?

 TimWait wait wait….I added that I wanted a woman who stands up for herself.  I think if you meet the right person, you’ll both be able to get away with doing a lot of the things you do on your own, just together.  And I think people should be selfish when they are looking for someone to date.  If you choose to share your life with someone, you should get what you want in return right?


Rita:  Have you ever been in love?

TimYeah, with a woman I sat next to through most of law school.  She had feelings too, but had been seeing someone else for years who she ended up marrying.  My rejection there was what really changed my mind about how I deal with relationships.  I know that love is subjective to each relationship, but I don’t think I’ve really ever felt the same way about someone since.  Man, that sounds like I’m damaged.  I’m really not.

Rita:  How did your experience with her cause you to change your approach?

TimI feel like I wasted a lot of time with her and that I set myself up for failure.  I should’ve known that I couldn’t have won her over.  I no longer overlook things like that and I’m more protective of myself.  Before I would just open up and allow myself to feel a certain way, now Im a bit more reserved.


 Rita:  If a girl would like to meet you, how can she best capture your attention? 

TimI had a woman email me on Facebook recently after we met at a book event.  I was definitely attracted to her when we met and we lost contact after the event was over so she took the initiative to find me online and shoot me a note.   That was pretty cool.

I’m really big on women asking me out.  I think aggressive women are hot and I’m usually too busy to pay attention to subtle signals that women might send.  So just approach me.  It’s that easy.



Rita:  So you like aggressive women, just not sexually aggressive?

Tim:   I have no problems with sexually aggressive women.  I just get mixed feelings about someone who wants to have sex within the first 90 minutes of me meeting them.


Rita:  The topic of “celebrating being single” has come up often on this blog.  How does Tim Young celebrate his singleness?

TimI take trips with “my favorite person…” me.  Generally they’re when I’m on the road for comedy, but I like to spelunk through towns alone and meet tons of new people.  I learn what’s cool in cities and generally go to some awesome places.  

I like being on my own and doing my own thing at my own pace.  It’s not a bad deal. 



 Rita:  On these trips, where you like to go out and meet new people, how do you do it? How do you approach? You know I agree fully with this concept, but so many people have a hard time approaching strangers…even if it’s just for friendly chit-chat.

TimI talk to everyone all the time.  It just comes with the territory of being a comic and constantly having to hustle.  I’ll sit at the bar in a restaurant or I’ll talk to people in coffee shops and at airports on the way in.  It’s odd for me to not know how to do that because I’ve done it for so long.  I guess what I would say to someone who needs to break out of their shell more is that the worst thing that can happen is that they scream and run away, so just go for it and talk to whoever you feel like talking to.


Rita:  When you travel for your shows, have you noticed a difference in the way that people in DC approach dating, as opposed to those in other areas of the country?

TimHell yes.  There are huge differences.  I think it has a lot to do with ratio of women to men in a city.  I get a frantic feel from women in NYC and DC.  Like they need to sign you to a long-term relationship deal as soon as possible.  Maybe because professional women outnumber men in those two cities.  My hometown of Baltimore happens to have the worst attitude of the women that I have met, just that they think they are something they are not.  The south is very much so the same stereotype of more women who are willing to be homemakers than professionals.  And you would always be shocked that women in Los Angeles, who are all for the most part strikingly attractive, but all look the same, are shocked to be hit on.  Did I cover all the regions there?  I bet I offended someone. 

DC also has that group of people with the “I’m better than you attitude,” who think they’re important but they don’t really know anyone…most people will know what I’m talking about.  Those women are unapproachable and don’t deserve to be approached.

Oh you can just assume that men react accordingly in those areas.


Rita:  What advice/encouragement would you give to someone who is single and looking?

TimWell, if you’re a guy, especially in DC, you have the best pool of successful, independent, attractive women to pull from. 

I always say go to your favorite place to hang out to meet the partner you want to meet.  Where better to meet them right? 

And never settle for less than what you’re worth.


Rita:  As you know, I’ve debuted a new feature, Rita’s Date Guide for Guys. What are some tips you have for guys in terms of how they can step up their game in the dating world?

TimDon’t pretend to be someone you’re not.  Don’t put on a show on a first date.  Be comfortable in your own skin.  I think the best way to step up is to calm down.  Let someone see you for who you are and not some sort of over-compensating jerk.  I hear the over-compensating jerk  line  a lot from female friends. 


 Rita:  Any tips for the ladies?

Tim:  Be aggressive when you meet someone that you want to know more about.  It’s whatever the term is for the decade of the twenty-tens…. It shouldn’t always be on a guy to ask you out.  Also, respect yourself.  Don’t tolerate someone or something that you know is beneath you.  



Rita:  What is your recommendation for a great DC date?

TimI don’t want to give my good one away, but I guess I can.  I have on more than one occasion walked the mall then had a late picnic in front of the Washington Monument watching the sun set on the Lincoln Memorial.  Bottle of wine and something from Whole Foods and the whole thing only costs you $30-40.  You can’t beat it.  Honestly, you can’t. 

And if I see anyone else out there who took this suggestion when I bring a date there, ya’ll better clear out.  I claimed it first.


 Rita:  How do you approach a gal who you want to get to know, to get her to go on this great date?

TimI walk up to her and say hi.  I generally have some sort of funny observation about something going on around her.  I also love to pick up the rebound shot.  If there is a woman I’m attracted to at an event or a bar, I think there is no better way to meet her than watch another guy strike out first from a distance, then drop in and make a witty remark about how she’s on a roll shooting guys down.


Rita:  What inspires you in life and love?

TimIn life I think it’s those people who have taken serious risks and succeeded.

In love it’s honestly one couple that I know, my friend Jeff Roth and his wife Brittany in Austin,TX.  I have never met a more equally matched couple who just live an awesome, happy, wacky life together.  I think everyone should be as lucky as them to find each other.   They are the best example of so many positive things about relationships that it shows me that there is such a thing as the perfect couple…and I want that for myself.


 Rita:  Thanks Tim for talking with me today. You touched on a few subjects that I know are hot buttons for ladies, like them making a move to ask a guy out! Will be interesting to hear their feed back. But thanks for being so open…want to go have sex?

TimHold on I think my phone is ringing.  Yup there it is right there, ringing.   I need to take this.  It sounds important, with the ringing and all.

 Rita:  And it’s not even 9/11….



Feel free to leave your comments on any of the topics above!  I want Pillow Talk to be an interactive forum where we can all relate to each other and learn from one another.  Have someone you think would give good “Pillow Talk?”  E-mail me at Rita@singlesinthesuburbs.com with their information!



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