Ask a Matchmaker: How to Dress for a Date

Deciding how to dress for a date?

To answer some of the most common dating questions, we sat down with The Setup’s style gurus: Genevieve Gresset, Heather Drury, and Jesse Turner. Here’s what they had to say about the power of dressing to impress.

Why is it important to dress well on a date?

Genevieve: You only get one chance to make a good first impression. On a first date, it’s important to make that one count!

Heather: Whether we realize it or not, our clothes can express things like our personality or background. Also, it’s usually one of the first things that someone notices about you.

Jesse: How you dress says a lot about you. It’s an unspoken form of communication.

Does attitude matter?

Jesse: Absolutely. Confidence is key!

Genevieve: Whatever you’re feeling in your clothes–it’s going to show. If you wore too little, you’ll feel cold. If you put on too many layers, you’ll get too hot. Maybe your date won’t notice your shivers or sweat, but these things will make you appear uncomfortable. Probably, your date will pick up on that.

Heather: It’s so important to be in the right headspace before going out on a date. Do what you need to do to get in a happy, flirtatious, and playful mood. For my female clients, I always suggest taking a moment to themselves before going out. If you can, try not to go on a date straight from work. First, go home, relax, and get in the right mood. Before a date, take a bubble bath, blast some pop music, and dance around in your room! These are fun, easy ways to help you relax and slip back into your femininity after a long day at the office.

How can I show off my personality through my clothing?

Genevieve: I have one female client who is absolutely amazing. She is a successful, independent, and strong woman with a vibrant personality. To prepare for her upcoming date, sent me five outfit options to choose from. Her friend suggested she go in the baby blue dress with a sweetheart neckline. Although she looked great in that outfit, it didn’t show off her character! I told her to go with the bolder choice–a dress exploding in bright reds and purples. This dress not only flattered her figure but honored her powerful personality as well.

Heather: I think color can be a powerful tool to express your personality without compromising your look. There’s no problem in sticking to a classic silhouette and experimenting with color.

Jesse: Your style should reflect who you are as a person. If you’re a happy, fun, person, that should be reflected in your clothing. The concept of “dressing your best” isn’t about being someone you’re not. It’s about putting your best foot forward so that you can get a second date.

What are the most common fashion mistakes you see clients make?

Genevieve: Women who are self-conscious of their size dress have a tendency to dress in all black. I’m guilty of this, too. We all have “fat” days sometimes! But, when you’re meeting someone for the first time, dressing in all black makes you look like you’re going to a funeral–not on a date.

Jesse: For some reason, a lot of my male clients love wearing socks and sandals. Men, please don’t do this! This combination instantly kills all sex appeal.

Is there such a thing as dressing appropriately for one’s age?

Jesse: Yes. There are some looks that a twenty-year-old can get away with that someone pushing 50 might want to avoid. It’s all about the context and the occasion.

Genevieve: I agree, but it’s important to dress not only for your age but for your energy as well. I recently signed up for a personal styling service called Stitch Fix. I told my stylist that I didn’t want to dress like a typical woman of my age. I wanted something mindful of my age, yes, but also my energy and lifestyle. The box she sent me was full of fun, playful, pieces that showed off my personality while still being age-appropriate.

What’s your most controversial fashion opinion?

Jesse: Hats are no go. I have one client who insists on wearing a fisherman’s cap on all his dates. After his dates, I’ll check in with his matches and ask how it went. They usually say he was nice. But, without fail, they all ask me if he is bald! This man has a head full of hair but because he was wearing the hat, that’s all his dates could think about.

Heather: And if a guy really is bald?

Jesse: Then be bald! Embrace it. Don’t try to hide it with a hat.

Genevieve: I suppose my most controversial opinion is that I actually like hats. I went on one date last summer where both of us wore hats. It made it all feel victorian and elegant. His hat was very cool!

Heather: Hats are one of those accessories where it depends on the context and situation. If you have a sense of style and you’re going for an outdoor date, then there’s no problem with donning a nice sun hat. But, if you’re sitting down at a restaurant indoors, it should be removed. It’s respectable and makes it easier to connect with your date.

What is your favorite fashion hack?

Genevieve: When it comes to dressing for a date, the best hack is to have your outfits ready to go. I tell my clients to have their go-to date looks on standby. That way, when a date comes up, you don’t have to worry about what you’re going to wear. It’s also a good idea to try on those outfits regularly. Make sure they still fit and look good on you.

Heather: Don’t get caught up following trends! Instead, focus on your individual features and stick to what works. Think about what parts of your body you feel most confident about. Try to pick clothing that highlights that part of your body and go from there. Once you figure out what clothing best compliments you and your and features, shopping becomes much easier.

Jesse: Before you go out, look in the mirror and ask yourself: “How approachable do I look in this outfit?” or “What does this outfit say about me?” If you want to make a great first impression on your date, thinking critically about your clothing is a good first step.

How do you help your clients to get out of their fashion comfort zone?

Genevieve: Wear it at home! Take pictures of yourself to see how you look from different angles. Maybe you like a certain outfit, but need some time getting used to it. That’s when you can wear it out for a night out with friends. Never use the first date to try out an outfit you’ve never worn before. Take it for a test run with friends or at home so that you get used to how you feel in it.

Jesse: I’ve always been slim. So, growing up, people would always comment on my size by telling me to eat a burger or something like that. thinking that it would disguise my frame, I started wearing baggy clothes. At the time, that type of clothing felt like a shield protecting me from other people’s judgments. Later in life, I switched up my style and started wearing tailored shirts and pants that actually fit. Now, I get compliments all the time on my style. I am more confident now that I’ve embraced my authentic self and started dressing in a way that actually compliments my figure–not hides it. So, I tell this to clients if I sense they need an extra push. Once you make that change, you’ll never regret it.

Heather: Just try it on! You don’t have to buy it. And if you do buy it, you don’t have to wear it. Just like meeting new people, you’ll just never know until you try.

I’m still learning the fashion basics. At what point can I trust my own sense of style?

Jesse: I think when you start to notice other people complimenting your style, that’s when you can feel confident in your choices. This is not to say that you should rely on the validation of others, but it is a good point of reference.

Genevieve: Your first inclination might be to seek the opinion of others. But, family and friends aren’t always trustworthy in these things. If they think something looks bad on you, they might find it hard to tell you the truth. As matchmakers, we have no problem being brutally honest. That’s what we’re here to do! So, take advantage of us as a resource. Send us photos and we will give you honest feedback.

Heather: The more you try something new, the more it becomes a part of who you are. If you ever feel insecure about a look, we are here to help.

Single Mom and son laughing while on basketball court

3 Tips for Dating As a Single Mom

Dating as a single mom is tricky enough without all the bad behavior we see online these days. As a single mom, you tend to consider the impact felt by your children before you even pause to think about your own feelings, but you deserve love and happiness too!

You should be as honest with your kids as possible when you’re ready to put yourself back out there since your decisions affect them directly. Even when you know instinctively you’re making the right move—they won’t always react the way you hope. So, do your best to prepare them for the coming changes so they don’t feel quite so off-kilter if and when they meet their future step-siblings. 

1. Manifest a Whole Family

Ron L. Dean, Licensed Marriage and Family Therapist, suggests you sketch out the silhouette of what your perfect family would look like. Don’t just manifest your dream date, go a little further. Imagine the ideal home you hope to create with this person.

Do you want more kids? Would your imaginary husband bring his own children into the relationship to create a blended family or is he flying solo? Is there a limit to the number of kids he has or the more the merrier? Are you open to having more children with him? How many?

Committing to this exercise will help you develop a blueprint in your mind. Keep in mind: this is only a guideline it will change overtime. This is meant to be a tool to help you discover what you want out of life, not to be used to get in your own way. 

Lillian and Clay each have a son and a daughter from previous marriages. When Lillian drew up her ideal family, she decided she only wanted one more child, if any. When she met Clay, her plan evolved to include both of his children, and she was happy to become a mom of four. But she quickly found out that even her evolved family didn’t mesh with Clay’s vision for the future. You see, Clay has his heart set on having five biological children.

If you do the quick math, that would mean Lillian would need to have three more kids with Clay. I would never reveal a lady’s age, but she’s tip-toeing the line of what would be considered a geriatric pregnancy. Not to mention: the gap between her original goal of 2-3 kids and Clay’s desire for 5-7. 

You know how they say sometimes love isn’t enough? If your dreams and your partner's dreams are in direct conflict with one another, and neither of you are willing to compromise—a breakup is imminent. 

2. Trust Your Intuition

This guy has to mesh into your entire life, and that means your kids’ lives too. If you sense something is off between him and your children, don’t ignore it. You should expect some growing pains as you transition a new person into your lives, but don’t dismiss real red flags. 

Listen to your gut.

Unless you have a pre-arranged agreement with their father, there is no set timeline for when you should introduce a romantic partner to your kids. Every relationship is different, and every child is unique. Only you can know when it’s the right time to bring them together.

It can be hard introducing friends and family but introducing children is always more difficult and can be hard for all parties concerned and very nerve wracking. It is also the most important decision you can make. Only introduce children if you are 100% sure that the new relationship is stable and serious enough to warrant the introduction. It can be very unsettling for children if they are introduced to many potential partners, the children should not be used as part of the vetting process. They should be the most important ones to consider when making the introduction and if they are not ready to meet the new partner, don’t push it. Always work at the child’s pace.”

-Genevieve Gresset, Master Certified Matchmaker & Relationship Expert

You don’t want to rush it and introduce every single first date you go on. A revolving door of strange men can feel confusing and scary for a little one, especially if they get attached to guys who don’t stick around. On the other hand, you don’t want to find yourself head over heels in love just to realize your kids hate the guy. You have to find the balance that works for your family.

One single mom suggests introducing male companions to the kids as a platonic friend. That way you can see how they engage and interact with him without being confused. If everyone gets along and things continue to progress, you can explain that you’ve decided to move out of the friend zone toward a more romantic relationship. 

3. Ditch the Single Mom Guilt

Take a deep, cleansing yoga breath.



Say this with me—I am a single mom, and I deserve happiness too. I’m allowed to feel sexy and take some time for myself. I’m going to treat myself to a new dress to wear on my setup.

Now pour yourself a glass of wine; you’ve earned it. 

"Kids need a healthy relationship role model. There’s pressure for moms to be born-again virgins, and sacrifice everything for their children. While this might sound noble, children learn a lot by observation, and it doesn’t teach kids what a good relationship—or dating life—looks like. I never wanted my kids to choose to stay home because they worried about me being lonely. It’s important that kids don't feel responsible for their mother’s social life. Plus, going out without kids on occasion gave me more patience with them when we were home together."

-Lara Lillibridge, Author of Mama, Mama, Only Mama: An Irreverent Guide for the Newly Single Parent—From Divorce and Dating to Cooking and Crafting, All While Raising the Kids and Maintaining Your Own Sanity (Sort Of)

According to Lara Lillibridge, dating as a single mom is similar to what dating was like as a teenager. You occasionally sneak out after everyone’s asleep, with a babysitter, of course. And you don’t want to be overheard on the phone, or caught canoodling on the couch.

If single mom guilt keeps you on homework duty in the evenings and you can’t bear to be away from them, consider utilizing the time you don’t have the kids more efficiently. Plan dates when they’re with their father, at practice, or sleeping over at a friend’s house. Schedule lunches throughout the week while they’re at school. Get creative with your time management and the kids will never miss you!

4 Ladies Pose for Camera- Womens Intuition

Myth or Magic: Women’s Intuition

We’ve all heard of women’s intuition. It’s an age-old phenomenon, but in recent years science has proven its validity.

Did you know that women make better spies, according to the CIA?

Okay, ladies, now let’s get in formation.

According to the British Journal of Psychology, Intuition is what happens when the brain draws on past experiences and external cues to make a decision—but it happens so fast that the reaction is at an unconscious level.

Intuition is our brain’s ability to draw on internal and external cues while making rapid, in-the-moment decisions. Often occurring subconsciously, intuition relies on our brain’s ability to instantaneously evaluate the situation and make a decision based on gut-instincts.

Judith Orloff, MD, is the assistant clinical professor of psychiatry at UCLA and the author of Guide to Intuitive Healing: Five Steps to Physical, Emotional, and Sexual Wellness. She said the following:

Just like the brain, there are neurotransmitters in the gut that can respond to environmental stimuli and emotions in the now—it's not just about past experiences. When those neurotransmitters fire, you may feel the sensation of butterflies or uneasiness in your stomach. Researchers theorize that gut-instinct plays a large role in intuition by sending signals to your brain. I teach my patients to always listen to their gut—that sixth sense that's telling you something might not be right—particularly if you're sensing danger. If you listen to it and you're wrong, you've lost nothing. Perhaps you took a longer route home or you ducked into a store until the feeling passed. If you don't listen to it and you're right, things could turn out very badly. More often than not, your gut is right, so listen up! It's always better to be safe than sorry.

Science suggests women's intuition is a product of evolution. Females with a strong ability to understand and predict the needs of their children and mates thrive over females with inferior senses.

Previous generations were often expected to be seen but not heard. Because of this, they developed a deep sense of observation by becoming hyper-sensitive to the feelings and nonverbal cues of others.

Women may exhibit more empathy, intuition, collaboration, self-control, and appropriate concern because of increased blood flow in the brain. Or as Dr. Daniel Amen, Founder of the Amen Clinics, put it:

“The female brain is wired for leadership.”

Perhaps they should have been listening to us all along. 

We are also better at showing our emotions through facial expressions, tone of voice, and body language. Whereas, men are better at hiding their emotions and maintaining a poker face. But often, we’re still able to decode your tells. 

Research on nonverbal communication skills shows women are better at reading facial expressions and emotions. As a result, we are more likely to pick up on the subconscious cues of others.

The University of Cambridge conducted an experiment where they showed 90,000 people photographs of only people’s eyes. They were then asked to conclude the person’s mood based on the appearance of the eyes in the photo.

Unsurprisingly, the ladies dominated. #GirlPower

When comparing MRI scans of brain activity, the female brain reveals an increased number of neural connections, making it more efficient. This helps with interpreting one’s social surroundings.

The male brain, on the other hand, is neurologically wired to be more logical, making it more effective at linking perception with action. This helps men be more intuitive. You guys also have better spatial intelligence, so stop making us navigate!

History and science both agree women’s intuition is more than just a myth. Listen to that little voice in your head; trust your gut.