Heather, 29
www.paperdollfashion.com

What fashion red flag should give me pause before I decide to start dating someone?
Too much hair gel. Anyone who's trying too hard with their hair is going to be trying too hard in life. You've got to watch out for those try-too-harders.

What can the art of clothing design teach us about relationships?
Don't fear interesting color combinations.

And don't undercharge — you're worth the money.

What's the best way to invite the guy I've been dating for a couple of weeks to go away for the weekend without making him think I'm trying to be his next girlfriend?
Ask him out to lunch, then just keep driving.

I really like the girl I recently started dating, but our makeout sessions feel forced. Is there potential for improvement?
I recommend kissing other body parts to break the ice. Like, you could nonchalantly kiss her bicep as she reaches up to grab a book off the shelf. Or kiss the hood on her sweatshirt — girls love it when you show affection to their clothing.

My best friend is perpetually single, and it's killing her. How can I help her get hooked up?
First, buy her some treats from Toys in Babeland — they'll come in real handy on those long and lonely nights. Then slather on the positive reinforcement. She is the most beautiful woman you know. She is more lovely and talented than any other woman you've ever met. She is worthy of love. Dammit, we all are! Let's all say it together: "I am worthy of a loving relationship." Damn, that felt good.

I told my new girlfriend I love the outdoors, but I don't. My idea of a good trip is a hotel with high-thread-count sheets and room service. Now she wants to go camping with me. What do I do?
Take her to a chic hot-springs spa that has surrounding natural beauty where she can traipse through the mud while you relax with your kombu-tini and watch TV in your four-star suite.

Elise, 33
www.OnTheInside.etsy.com

My wardrobe is pathetic. I have a date coming up and my budget is near zero. How can I look good?
Raid a friend's closet, then buy a new pair of earrings.

My boyfriend has no style. How can I get him to become more fashion conscious?
Surprise him with a couple of items you bought for him that you think he would be receptive to. But don't ever be embarrassed because of the way someone dresses. When I meet a fabulous person, it doesn't matter what they're wearing.

I really like the girl I recently started dating, but our makeout sessions feel forced. Is there potential for improvement?
There are times where it can get better with practice when you start to know each other more, but generally, if it's not there, it's just not there.

Everything in my relationship with my boyfriend has changed since he brought up marriage, and I said I wasn't sure. I explained that no didn't mean "no forever," but he still seems upset. What can I do?
I'm sure his feelings are hurt. Committing to a relationship is a really big step, and when one person feels like that's where it's going and the other one still isn't sure, it can create some distance. Let him know you truly care for him, make him feel wanted, and he should come around.

I told my new girlfriend I love the outdoors, but I don't. My idea of a good trip is a hotel with high-thread-count sheets and room service. Now she wants to go camping with me. What do I do?
If it's something she really wants to do, just do it. Get the coziest sleeping bag you can find, and pack some sushi and a big bottle of wine.

Keith, 26
www.filthygorgeous.com

My boyfriend is funny, but sometimes he's too crass, especially around some of my more conservative friends. How can I let him know that some jokes are inappropriate without seeming like I'm trying to censor him?
In a group situation, have one of his friends whom he's known for a long time say something about it to him. Or just do it in jest. It's always easier to take something if doesn't come off as combative.

My wardrobe is pathetic. I have a date coming up and my budget is near zero. How can I look good?
Reinvent some of your old stuff. This doesn't mean sewing or tailoring, but mix and match. Pull from your favorite magazines, and find a look.

My boyfriend has no style, and sometimes it's embarrassing to be out with him. How can I get him to become more fashion conscious?
Give clothes. It's about him feeling comfortable. If he's a t-shirt guy, don't get him button-ups. Get him progressive, stylish t-shirts. Take him shopping, buy it for him, and when he does look stylish, compliment him.

Everything in my relationship with my boyfriend has changed since he brought up marriage, and I said I wasn't sure. I explained that the no didn't mean "no forever," but he still seems upset. What can I do?
That's a hard one for me. I don't date someone if I don't see a future there. "No" is a strong word and honestly, if someone gets a no, they're going to start backing off. You need to step up and show more affection than normal if you want to save this.

What fashion red flag should give me pause before I decide to start dating someone?
If they're wearing a hat with a feather, steer clear.

What can the art of clothing design teach us about relationships?
You can't put just any two random things together and expect it to work.

Elise, 23
www.ThreadsByElise.etsy.com

My wardrobe is pathetic and I have a date coming up. My budget is near zero. How can I make sure I look good?
Thrift stores. Find a blouse with a vintage design. Secretary shirts are great flirty-but-not-too-revealing first-date clothing.

What are your top-three no-wiggle-room dating rules?
1) Always hold the door for a chick, even if she says she doesn't like it. It is the only thing that still makes a modern male a gentleman. 2) Call back when you get the voicemail. Don't wait. 3) Don't use your cell on a date.

The guy I'm dating has an apartment that's a total mess. I don't even like being in there. How can I get him to clean up without sounding like a nag?
Bring it up casually. I'm the messy one in my relationship, and my boyfriend brought it up to me one night in a very low-key way. We talked about it, and I changed my ways.

My best friend is perpetually single, and it's killing her. How can I help her get hooked up?
I think the problem isn't that she doesn't have a boyfriend, it's that she's afraid of being alone. Talk to her about the fact that she doesn't always need someone with her to be happy in life. Go out with her and do fun things to get her mind off of the thought of wanting a significant other.

What fashion red flag should give me pause before I decide to start dating someone?
I've found that if a guy wears clothing with holes in it, or has messy hair, you are probably going to be picking up the tab. n°