Hi Liara,

My boss’s daughter—who is also my coworker—has been very flirtatious with me. I can’t tell if it’s a good idea to pursue something with her. What do you think?

Thanks,
M

“A little work crush can make heading to the office a lot more exciting, and it doesn’t need to be anything more than that!”

Hi M,

Unfortunately, your message is so short that it’s hard to know what the dynamic is exactly. I have a few questions: Are you sure she’s flirting with you? Are you her superior at work? How important is this job to you, and how difficult would it be for you to find similar work elsewhere? Do you live in a small town, or a big city?

If you’re her superior—don’t do it. Even if she’s the daughter of your boss, if you’re in a position of power over her, I don’t think it’s ethical to pursue.

If not—maybe it’s fine! Do you work together directly? If you work in different departments and don’t see each other all the time, it’ll be easier to handle. But given that she’s been “very flirtatious” with you, I’d guess that the two of you are working in pretty close contact. Spending so much time together can put a lot of strain on a relationship!

The most important question: How much do you care about your job? If you don’t mind working elsewhere if the situation heads south, maybe it’s fine—if you’re working in Manhattan at a Starbucks, for example. But in another field—especially if it’s close-knit—I’d be very wary of trying anything. People talk.

If you really like her, maybe ask her parent—your boss! This could come off as corny or old-fashioned, but it might make sense to tell them, Hey, your daughter is really cool and I have a crush on her. Is it okay if I take her out on a date? It’s probably better to be open with them about the situation—most people will be way more upset if they find out about something like this after the fact. It’s a good way to test how smart of an idea it is, anyways; if you’re nervous that asking will piss your boss off, imagine how pissed they’ll be if they find out from someone else!

Even if you think it’s unwise to make a move, if she’s being a flirt, then you can go ahead and flirt back. A little work crush can make heading to the office a lot more exciting, and it doesn’t need to be anything more than that!

Best of luck!
Liara

Hi Liara,

Would it be weird to tell someone how much they mean to me? I don’t mean this in a romantic sense—just unsure of how appropriate it is to express something like that.

Help!
A

“Many people fear expressing affection towards their friends, like it’s a strange thing to tell someone you love and care about them, unless you’re romantically involved. This is such bullshit!”

Dear A,

This is such a sweet question! I think it’s absolutely fine to tell people things like this. I used to really struggle with opening up—I worried it would make the other person uncomfortable, or place undue stress on our relationship.

But experience has taught me that people love hearing that they’ve played an important role in your life. It encourages them to keep doing what they’re doing. In fact, these days, I go out of my way to tell people how important and special they are to me, and emphasize that I really value them in my life. We all have our down days, and hearing words like this can truly help people push through. Even if you think someone is doing great, they might have private struggles. During tough times, it’s especially important to hear words of love and encouragement.

Many people fear expressing affection towards their friends, like it’s a strange thing to tell someone you love and care about them, unless you’re romantically involved. This is such bullshit! My friendships have always been the most important relationships in my life; many of them have seen me through so many changes. Lately, I’ve gotten into the habit of celebrating anniversaries; if we’ve been friends for five years or more, I think it’s sweet to go out for dinner to celebrate.

Life is short. Don’t hesitate to express words of affection and care! Accidents happen, so err on the side of love! If someone judges you for it, they’re not worth your friendship anyways.

Love,
Liara

Hi Liara,

I really admire your sense of style. I feel like I have no idea how to dress! My closet is full, but it always feels like I have no options when I need to get dressed up to go out. Where are your favorite places to shop?

Help!
G

“Get everything tailored. Tailoring can seem labor-intensive and expensive. Who has the time and money to drag everything over to a shop? But it’s always worth it.”

Hey G!

My grandmother raised me with a few very important rules to follow when buying clothing.

One: Buy clothing according to your tastes, not according to trends. Figure out which styles you like. Are you into goth shit? Cute ’60s mod? Funky ’70s fits? I highly recommend getting familiar with different trends over time; you’ll find that a lot of styles and silhouettes tend to repeat themselves! If you develop your own unique style that’s cohesive, you don’t need to worry about whether skinny jeans or mom jeans are in—you’ll know what you like best. Some years, your style will be “out” and it’ll seem like nothing in the stores suits you! But the beauty of trends is that they always circle back around, and eventually there’ll be plenty of options. Plus, if you buy vintage, the stores will be flooded with your favorite pieces, even when they’re no longer hot.

Two: Figure out your cuts. I really love 1920s flapper dresses. I think they look amazing. But unfortunately, I am rather well-endowed in the chest and those dresses were designed for people on the itty bitty titty committee. Obviously, I think everyone should wear whatever they want, regardless of the rules, but I don’t like how they sit on me. So I don’t buy them! Learning which cuts suit your body type relieves a lot of stress while shopping; I like wearing dresses with short hems, oversized silk shirts with slim sleeves, and high-waisted pants.

Three: Quality over quantity. Many of my friends who complain they have nothing to wear will buy massive hauls off Shein, then complain that they don’t like how anything looks on them… And I’m like, Duh. The fabric is thin, and the underpaid worker making the garment simply doesn’t have enough time to finish the seams with care. For well-made basics, I really like Uniqlo and Everlane. Yes, they’re “boring,” but they’ll last. If you know your materials, it’s easier to find cheap gems at the vintage and thrift store, too. Look for cashmere, silk, linen, and cotton, and check to see how the seams are finished. I often will invest in only one new outfit per season. Eighty dollars for a nice silk shirt can seem like a lot, but if you’re only spending $80 total on clothing that month, it’s really not that much.

Four: Get everything tailored. Tailoring can seem labor-intensive and expensive. Who has the time and money to drag everything over to a shop? But it’s always worth it. If you’re buying fewer items that you really treasure, then you’ll be keeping them for a long time. It’s worth it to have them taken in or let out where necessary. You’ll look better, and you’ll feel more comfortable, as well! If a piece is damaged, you can have it taken in to be repaired, and it’ll usually be less expensive than replacing it.

Five: Prioritize comfort. If clothing isn’t comfortable, you’ll feel and look miserable wearing it. If a dress is itchy, don’t buy it. If your cute winter jacket doesn’t keep you warm, replace it. Obviously, sometimes we must suffer for fashion and commit to a look. But, in general, you’ll be way more likely to wear your hot outfits if they feel good, too! This is a great way to pare down your options while shopping. One of my go-to outfits for brunch is a pair of silk pajamas and some fun heels. It’s a look, and it’s also incredibly comfy!

Dressing according to these rules leaves a great deal of room for personal expression. It also allows you to develop a personal relationship with clothing. I still wear some pieces that I’ve had since school—one of them is a dress that my grandmother made for me! When you wear an item that often, you really get familiar with it; you know how to style it, what to pair it with, whether it’ll be too hot or too cold for the weather. That, in my opinion, is the key to truly dressing well.

Love,
Liara