Ashley Woolley / 25, Chicago, IL
I'm a country girl at heart living big-city life?I firmly believe that life is better unfiltered and spontaneous. :)


Ashley Woolley's Profile Details

  • Hometown: Urban
  • Relationship status: Single
  • Hair Color:
  • Level of education: College
  • Cash flow: Comfortable
  • Mode of transportation: Taxi
  • Work: Career
  • Current living situation: Lone Wolf
  • Outlook: Optimist
  • Politics: No Thanks
  • Religion: Disorganized
  • Socialization: Outgoing
  • Intravenous temperature: Cool-Headed
  • Time to get ready: More than 15 minutes
  • Intensity: Driven
  • Applicable stereotypes: Fashionista,Outdoorsy,Arty
  • Makeup stance: Never leave the house without it
  • Hang Out:
  • Flavor of humor: Witty
  • Her food: 3/5 from strict vegan(1) to meat loving(5)
  • I am a...: 3/5 from nice girl(1) to bad girl(5)
  • Kind of guy she goes for: Normal
  • Dating style: Plays the Field

Ashley Woolley's favorite drink

Traditional Cuba Libre

View Recipe >


Questions Ashley Woolley has answered:

How much gym time is right for a guy?

Her answer: As much as he needs to keep up with me
I like guys who value health and take care of themselves without obsessing too much about it.

Other questions from Dude 101 What's your version of fun outdoor activities?

Her answer: An invigorating hike
Getting outside and challenging each other can be a great adrenaline rush that boosts your closeness

Other questions from Dating
When it comes to tattoos, what's unacceptable subject matter?

Her answer: Ex-girlfriend's name
How could that possibly be acceptable??

Other questions from Style What do you think of guys who cook?

Her answer: Always a good look
Hey, at least he tries! Brownie points for effortóeven if his brownies burn.

Other questions from Dating
When out to dinner, what looks good on a guy's plate?

Her answer: Anything, as long as it's not loud and messy
I like a guy who will try anything once. But please chew with your mouth closed.

Other questions from Dating
During the courtship phase I like a guy who:

Her answer: Plays it cool, but is clear about his interest
It's intriguing to be pursued, but we want to know you care.

Other questions from Dating
In matters of heart a guy should be:

Her answer: Cool-headed
I'm most comfortable with easy-going and level-headed guys.

Other questions from Dating
When the two of you are together his eyes should be:

Her answer: Taking in the beauty of the world, me included.
Eye contact is greatóstaring like a deer in the headlights is just creepy.

Other questions from Dating
What age do you think people should get married?

Her answer: There's no particular age
When they're confident that they're ready and doing it for the right reasons.

Other questions from Dating
When do you make a long-distance relationship short-distance?

Her answer: Why do I have to move? He should come to me.
I love my job and city. If he loves me enough, he'll come here.

Other questions from Dating
Are flowers still appreciated?

Her answer: Yes.
Appreciated, yes. But do something a little creative if you want to impress her.

Other questions from Dating
How long before jewelry is a required gift?

Her answer: Marriage.
Give her something thoughtful. If it happens to be jewelry, so be it. :)

Other questions from Dating
Are you still thinking about your ex on this Valentine's Day?

Her answer: Yes.
Unless I'm with someone else.

Other questions from Dating
Is it sleazy to pick up lonely single ladies on Valentine's Day?

Her answer: Nope.
It's only sleazy if you TREAT her like she's a 'lonely single lady.' Be nice.

Other questions from Dating
My lady claims she doesn't care about Valentine's Day. Is this a trap?

Her answer: Yes.
She probably doesn't want to put pressure on you, but she will likely appreciate a little effort.

Other questions from Dating
Regarding the gift of lingerie...

Her answer: Cool.
If you're already sleeping together.

Other questions from Dating
We've been dating for a week, and I surprise you with a weekend get-away in the country. Is that...

Her answer: Creepy.
Too soon. Romantic if you wait at least a few months.

Other questions from Dating
Is Valentine's Day a good day for a first date?

Her answer: No.
Too much pressure!

Other questions from Dating
Do I have to clean my feet in the shower, or do they clean themselves by the water that runs down?

Her answer: C'mon. Wash your feet.
Look at the floor of your shower - how clean is it? You could answer your own question.

Other questions from Dude 101 What's your take on fidgeting?

Her answer: Intensely annoying
Please. Stop. Moving. Your. Leg.

Other questions from Dude 101 What do you think when you see two men engaged in debate?

Her answer: “Ooh, sexy.”
An intelligent debate is sexy. A drunk brawl over a girl at a bar is unattractive.

Other questions from Worldy-Wise Does she want pleasantry, or honesty?

Her answer: Can you not be pleasant and honest?
Aim for a good balance.

Other questions from Mr. Manners How important is it that a guy knows how to make a fancy cocktail?

Her answer: Not at all
When in doubt, vodka soda!

Other questions from Nightlife How important is it that a guy knows how to make a fancy cocktail?

Her answer: Not at all
As long as he can open a bottle of wine.

Other questions from Nightlife Who controls the music in the car?

Her answer: Full democracy
Let's go for a mix.

Other questions from Mr. Manners What's the best Scorsese movie?

Her answer: Goodfellas
But not extremely attached to any of the above.

Other questions from Worldy-Wise Sharing of toothbrushes: okay or not okay?

Her answer: Use your finger
Even if I love you, I don't love your plaque.

Other questions from Mr. Manners She starts moving toward the dance floor, what do you do?

Her answer: Show her your moves
Shake it, baby! Show her you can have fun.

Other questions from Dude 101 Is it possible for me to ask out a bartender, barista, or waitress?

Her answer: It is possible, but not recommended.
Never think you're the first customer who's asked her out. And she's probably flirting for tips.

Other questions from Nightlife I just lost my job. How long do I have until my girlfriend starts to get antsy?

Her answer: Depends how hard you're trying to find a job
And it depends on how much you have in savings.

Other questions from Style How do you feel about Iowa?

Her answer: Hate it.
GO ILLINI!!!!

Other questions from Worldy-Wise Should I always ask you about your day?

Her answer: If I look like I need to talk.
Only ask if you'll actually listen to the answer.

Other questions from Mr. Manners How long can we talk about politics?

Her answer: Thirty minutes.
On a first date, 0 min. In a relationship, express our opinions, but I don't want to argue about it.

Other questions from Mr. Manners We're leaving. What do I do with my almost-finished beverage?

Her answer: Finish it.
Go for it—I'm going to finish mine!

Other questions from Nightlife If I'm a starving artist, do we have a chance?

Her answer: If you know how to be creative on a date.
Money is not necessary to impress me on a date, but effort is.

Other questions from Success To what extent should our interests overlap?

Her answer: We should be teaching each other.
I don't want to date my twin. Teaching each other can keep the interest and attraction alive.

Other questions from Worldy-Wise What's the proper cologne intensity for a guy?

Her answer: When I'm close to you.
Please don't be that guy in a cloud of cologne—it's meant to attract, not repel!

Other questions from Dude 101 Beatles or Stones?

Her answer: Beatles
It's feel-good music!

Other questions from Worldy-Wise Is it okay if I point out people's grammar mistakes?

Her answer: It's all in good fun
I'll join right in!

Other questions from Mr. Manners How often should I be talking to my mom on the phone?

Her answer: Once a week
No rules here - every family is different, so do what works for you.

Other questions from Dude 101 Can I eat garlic?

Her answer: Not if you're looking to get kissed.
Same goes for onions.

Other questions from Success If your dad has a sweet business, can/should you have him hook me up?

Her answer: Maybe?
If he gives you the name of a great contact, go for it! But I wouldn't recommend working for him.

Other questions from Success Does having many jobs on my resume look good or bad?

Her answer: What kind of jobs are we talking about?
If your job is accompanied by volunteering and freelance, you'll seem well-rounded and driven.

Other questions from Success Do you want to hear me talk about my (awesome) job?

Her answer: Talk about your other interests first
Wait until I ask about your job. I want to know about your life, not your resume.

Other questions from Success Who should be wearing sexy underwear?

Her answer: The lady.
I feel hotter in sexy underwear. He's always hot in boxer briefs.

Other questions from Style Should I wear a blazer with my jeans?

Her answer: Depends where you're going
This is fine at a club, but wear a button-down to dinner instead.

Other questions from Style Do women notice when a man has a nice wallet?

Her answer: Nah, doesn't matter.
Pick your battles, ladies. This one can slide.

Other questions from Style When should a guy use gel in his hair?

Her answer: Depends on his style.
Just don't look like a cast member of 'Grease.'

Other questions from Style When are athletic socks acceptable?

Her answer: Only when playing sports.
Ankle socks are better.

Other questions from Style How should we celebrate our one-night-stand?

Her answer: A high five before I get in a cab
Let's not pretend it was something it wasn't!

Other questions from Dating
If a girl waxes, a guy should trim. True or false?

Her answer: TRUE
Tit for tat! And it's just good bedroom behavior.

Other questions from Dating
What's the acceptable level of ex-interaction?

Her answer: Annual calls are okay.
As long as you're on mutual friend-only terms.

Other questions from Dating
Who pays for contraception?

Her answer: The girl
I like to take personal responsibility for my body and choices.

Other questions from Dating
How intensely do you Facebook stalk?

Her answer: I want to see pretty much everything
I've noticed that guys who have long, intricate profiles are almost always self indulgent!

Other questions from Dating
Can I go to a strip club with my buddies?

Her answer: Yes, but no lap dances.
You can look - but don't you touch!

Other questions from Mr. Manners We're telling stories. How do you feel about stories including my ex?

Her answer: Tell the story, leave her out.
Let's make good stories of our own.

Other questions from Mr. Manners How much should I tip the waiter?

Her answer: Twenty percent
Always.

Other questions from Nightlife Can I leave my phone out when we're out at dinner?

Her answer: No.
Show a little respect.

Other questions from Nightlife You're my boss, and you're hot. Where can we go from here?

Her answer: No can do. Pens OUT of company ink.
Never date a coworker. Too messy, too close, too awkward.

Other questions from Success When a girl tells you how many partners she's had, it's usually...

Her answer: We're all a bunch of liars.
It usually depends on how many she thinks you've had.

Other questions from Dude 101 What should be manscaped?

Her answer: Everything.
Keep it under control—you won't regret it.

Other questions from Dude 101 What type of body is best for a guy?

Her answer: Muscly and cut.
I LOVE a man with muscles!

Other questions from Dude 101 Does my collection of comic books count toward my knowledge of art and culture?

Her answer: Ummm, no. Comic books are for children.
Not your most attractive interest...

Other questions from Worldy-Wise How long should you date before asking her on a weekend away?

Her answer: Couple months
This is a great way to get to know each other better and break out of your normal dating routine.

Other questions from Worldy-Wise What's the sexiest kind of facial hair on a guy?

Her answer: Clean shaven
I want NO part of anything that falls into the 'get creative' department.

Other questions from Style What kind of underwear is best on a guy?

Her answer: Boxer briefs
Ooooh yeeaaaaaa ;)

Other questions from Style When does sexual history come up?

Her answer: Once we’re ‘serious’
Let's not reveal the 'roster' too soon!

Other questions from Dating
Do you Google search your date before meeting up with them?

Her answer: Yes
Sometimes.

Other questions from Mr. Manners Which way does toilet paper go?

Her answer: Over
Heck, I'll be happy if he replaces the roll!

Other questions from Dude 101 How frequently do you think guys look at porn?

Her answer: Once a week
At LEAST once a week...depends on his age, living situation and how often he gets laid.

Other questions from Dude 101 Bros before hoes. Your thoughts?

Her answer: There’s a time and a place
At guys' night. But don't keep her on the back burner for long, or you'll be the one getting burned.

Other questions from Dude 101 What's the maximum number of days I can wear the same underwear?

Her answer: Seriously?
ONE!

Other questions from Dude 101 My buddy just broke up with his (awesome) girlfriend. When can I ask her out?

Her answer: Never. It’s guy code.
Can you seriously think about them being formerly naked together and not care?

Other questions from Dude 101 My best buddy told me a secret. Should I tell my girlfriend?

Her answer: If you love your girl, tell her.
Unless she's a blabbermouth.

Other questions from Dude 101 I'm at dinner with no cash and they don't take plastic. What now?

Her answer: Never, ever show up to dinner without cash.
Make like a Boy Scout: be prepared.

Other questions from Dude 101 What's your take on public broadcasting?

Her answer: Indispensable
What's wrong with public broadcasting?

Other questions from Worldy-Wise How do you feel about Judd Apatow?

Her answer: Hilarious
And brilliant.

Other questions from Worldy-Wise What's the most important thing a guy should be reading?

Her answer: Anything at all
As long as he's learning something.

Other questions from Worldy-Wise I get all my news from Jon Stewart. Is that OK?

Her answer: Nope.
Let's branch out a little...

Other questions from Worldy-Wise Going to open-mic night makes me...

Her answer: Cooler
I LOVE guys with guitars!

Other questions from Worldy-Wise Travel to a foreign country is...

Her answer: A good way to have lots of great stories
And exciting!

Other questions from Worldy-Wise Does listing the places I've been make me seem pretentious?

Her answer: No
Making a list of places you want to go is better.

Other questions from Worldy-Wise What should be in my fridge?

Her answer: Beer is enough
We can always order in.

Other questions from Mr. Manners When it comes to PDA, which base is acceptable in public?

Her answer: 1st
But sex in a semi-public place can be really hot.

Other questions from Mr. Manners How important is it for a guy to notice your new haircut?

Her answer: Definitely
Changing our hair is a big deal for us—just act like you care and humor us.

Other questions from Mr. Manners When is public flatulence OK?

Her answer: Never
Aren't there meds for 'legitimate problems'?

Other questions from Mr. Manners Do I open the doors, or does she?

Her answer: You do.
Try. But I might not always let you.

Other questions from Mr. Manners My friends are getting married and I'm broke. What should I get them?

Her answer: A handwritten card shows that you care.
This is an emotional time for them-sentiments mean much more than flatware they'll never use.

Other questions from Mr. Manners What's the best birthday present to give to a male friend?

Her answer: A night on the town.
Have fun together!

Other questions from Mr. Manners What's the best hangover cure?

Her answer: Brunch!
Mimosas, anyone?

Other questions from Nightlife Two good drinks or four crummy drinks?

Her answer: 2 good
Depends on the night...

Other questions from Nightlife Should I buy shots for the cute girls at the bar?

Her answer: Yes. But they’re just using you.
Hey, you asked!

Other questions from Nightlife I've spilled red wine on myself. What do I do?

Her answer: Club soda, stat!
And I'll wipe it up for you ;)

Other questions from Nightlife Liquor before beer, in the clear: true or false?

Her answer: Neither
I don't like drinking rules.

Other questions from Nightlife Is checking my coat lame or just good sense?

Her answer: No, why have the extra baggage?
Bonus points if you offer to check mine, too.

Other questions from Nightlife What looks best in a guy's hand?

Her answer: Shots!
I like a guy who can party!

Other questions from Nightlife Do you care what a guy does for a living?

Her answer: Not really
This matters to an extent—it would be almost impossible to date a gyno...or a stripper...

Other questions from Success Does my title matter?

Her answer: No
Unless your title is 'King'...

Other questions from Success What financial level should a guy be at compared to you?

Her answer: Equal
But his drive is more important than his money.

Other questions from Success Drinks with coworkers: important part of getting ahead?

Her answer: Yes, it’s a must.
Maybe not quite a must, but a definite plus and a great chance to discuss issues one-on-one.

Other questions from Success I'm negotiating for a raise. What's my first move?

Her answer: Put together a list of your recent accomplishments.
Always be able to support your statements.

Other questions from Success I hate networking events. What should I do?

Her answer: Get over it! It’s a necessary evil. Talk to people.
I like someone who's able to break out of his comfort zone.

Other questions from Success How should I ask for a first date?

Her answer: In person
Grow a set.

Other questions from Dating
First date: would you rather a guy overdress or underdress?

Her answer: Overdress
This shows that you put a little effort into the date.

Other questions from Style When is a mustache a fail?

Her answer: Every time
Mullets fail, too.

Other questions from Style Two polos at once?

Her answer: Stupid
And please don't wear your sunglasses at night.

Other questions from Style Skinny jeans (for him): in or out?

Her answer: Out
Please don't suffocate the family jewels for this awkward look.

Other questions from Style Should socks match the blazer or the slacks (if they're different colors)?

Her answer: Slacks
Do people actually match their socks to their blazers??

Other questions from Style Pointy shoes: in or out?

Her answer: In
But I also love a good pump with a rounded toe!

Other questions from Style What's your take on guys having a sense of style?

Her answer: It’s an absolute must
It's a must that he has a little style, which shows that he has his act together.

Other questions from Style Could you date a guy if you didn't really like his mother?

Her answer: Yep!
I'm not sleeping with his mommy.

Other questions from Dating
Asking out a stranger you see every day: weird or romantic?

Her answer: Romantic
Romantic if there have been eye connections; creepy if without previous non-verbal communication.

Other questions from Worldy-Wise Asking out a stranger you see every day: weird or romantic?

Her answer: Romantic
Unless he's stalking you...

Other questions from Worldy-Wise Do you believe in love at first sight?

Her answer: Maybe?
I'll let you know if it happens.

Other questions from Dating
I prefer guys that are...

Her answer: Successful
I'm an extremely driven person and I can't be the only one in the relationship who is career driven.

Other questions from Dude 101 I prefer guys that are...

Her answer: Strong
Emotionally strong. Physically strong. Strong-willed.

Other questions from Dude 101 I like guys that are...

Her answer: Taller than me
I like a tall drink of water. :)

Other questions from Dating
Bald spots are...

Her answer: A turn-off
But comb-overs are much worse!

Other questions from Dating
How many dates before I can invite a girl up to my place?

Her answer: Three
Three is only an average - sometimes things develop more slowly, and sometimes I just can't resist!

Other questions from Style How have you been this year?

Her answer: A little of both
Depends on your definition of naughty...

Other questions from Dating
Do you have a set limit on how much you're going to spend on gifts for your partner?

Her answer: We've never talked about it.
We've always had a reasonable but unspoken ballpark price for gifts.

Other questions from Dating
Black Friday shopping: Drag him along or fly solo?

Her answer: Fly solo
I NEVER drag him along. I get more done without him, and he won't be there to complain.

Other questions from Dating
Where are you headed for the holidays?

Her answer: My parents
We don't see our families very often, so we head to our respective hometowns.

Other questions from Dating
During the holidays I indulge too much in:

Her answer: Shopping
Shopping, partying, and sweets!

Other questions from Style What should he contribute at Thanksgiving?

Her answer: Carving the turkey
My grandfather always use to assume this role, so it's nice if he steps up to the job.

Other questions from Dating
Wintertime is for:

Her answer: Hitting the sack
I'm a cuddler in the winter -- give me a fireplace and hot cocoa, and I'm happy.

Other questions from Dating
During their annual Thanksgiving Day game, the Detroit Lions are going to:

Her answer: Lose
Go Bears!!

Other questions from Dating
The holidays are about:

Her answer: Family time
My family loves spending the holidays together; it's really important to us.

Other questions from Dating
Where are we going on the first date?

Her answer: Somewhere new
Trying new places together makes it an adventure!

Other questions from Dating
How long after a serious break-up should you start dating again?

Her answer: About a month
It depends on when you feel ready. There's no set standard -- go with your gut (and heart).

Other questions from Dating
Can exs be friends?

Her answer: Yes, I've managed to make the transition.
Sometimes, especially if the breakup was cordial.

Other questions from Dating
Where will you meet your husband?

Her answer: At a friend's party
If I knew the answer to this, I would be married!

Other questions from Dating
When is it appropriate to change your Facebook relationship status?

Her answer: As soon as we break up
I have nothing to hide. If we break up, I change my status.

Other questions from Dating
How long before a guy can be your date to a wedding?

Her answer: After we've gone out a few times
But if it's a family event, give it more time.

Other questions from Dating
How important is it to date someone of the same religion?

Her answer: Somewhat important
Minor differences are OK, but I want us to agree on how we raise our children regarding religion.

Other questions from Dating
How important is it to date someone with the same political views?

Her answer: Somewhat important
We just need to respect each other's opinions and lifestyles.

Other questions from Dating
Sexting: Hot or not?

Her answer: Hot
Only if you're POSITIVE that only he will see it.

Other questions from Dating
Do you use your parents as a model for relationships?

Her answer: Nope. I have my own style.
There's no great model for a relationship. Do what's best for the two of you.

Other questions from Dating
NFL Quarterbacks

Her answer: Tom Brady
I do love a man in uniform.

Other questions from Style What's the most attractive band member?

Her answer: Front man
Singers and guitarists are both so sexy!

Other questions from Nightlife I like my spice:

Her answer: Spicy
I like to crank up the heat, but let's not burn off my taste buds with atomic.

Other questions from Style Would you date a guy with kids?

Her answer: No way. Too much baggage there.
This isn't black and white for me, but I'd be very hesitant.

Other questions from Dating
Guys who play video games:

Her answer: He can play with his joystick alone
Not a fan of video games.

Other questions from Dude 101 Are you a cat person or a dog person?

Her answer: Cat person
Love my cat! I work long hours and don't have time to take a dog outside several times a day.

Other questions from Dude 101 Can a partner have more shoes than you?

Her answer: Yes. He's got style, and I dig that.
But good luck trying to have more shoes than I do!

Other questions from Dude 101 Geek chic. Can a man rock a nerdy look with you?

Her answer: I draw the line at pocket protectors
Smart is sexy, but too nerdy is not.

Other questions from Dude 101 Sarcastic people are:

Her answer: Funny
In moderation...

Other questions from Dude 101 Twilight

Her answer: I don't watch it
Too much of a teen drama...

Other questions from Style If we're commuting together:

Her answer: Meet me at the subway station
I always take the subway. Let's go together!

Other questions from Dude 101 Mad Men (ladies)

Her answer: I don't watch it
This is one show I need to start watching!

Other questions from Style Pizza style:

Her answer: Deep Dish
I'm definitely a Chicagoan.

Other questions from Style Taco style:

Her answer: Soft shell
But quesadillas are even better.

Other questions from Style Absolute favorite genre:

Her answer: Country
I'm a total country fan, but I like a little of everything!

Other questions from Style What was the best decade for music?

Her answer: 90s
But 80s rock is pretty darn awesome.

Other questions from Style True Blood

Her answer: Bill
Sexy, mysterious, and heroic...yum.

Other questions from Style Going to a concert on a date:

Her answer: Awesome idea!
This is fun and keeps the pressure minimal. Go somewhere quiet after to have a drink and talk.

Other questions from Dating
How do you feel about stay-at-home dads?

Her answer: I'm all for it
I'd rather work than stay home, so this would be great!

Other questions from Dude 101 Better job:

Her answer: Start-up
There's usually more growth potential and responsibility available.

Other questions from Dude 101 Is it better to have love or money?

Her answer: Love
Both is great, but love trumps money hands down.

Other questions from Dude 101 How far would you move for a dream job?

Her answer: Around the world
To me, my career defines a huge part of my life's happiness. I'd go almost anywhere!

Other questions from Dude 101 Sushi style:

Her answer: Rolls
All of the above! LOVE sushi.

Other questions from Style What's his kitchen skill-level?

Her answer: Roasted chicken
I really respect a man who can cook.

Other questions from Dude 101 When something breaks:

Her answer: I can fix it
I'm really independent -- why do I need him to do it?

Other questions from Dude 101 Eco-conscious guys:

Her answer: Separate the paper from the plastic
I live in a high rise, so the compost pile is not an option!

Other questions from Dude 101

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