Stefanie Safran

Dating Coach & Matchmaker

Stefanie Safran is a Dating Coach, Matchmaker, and the Owner of Stef in the City, a Matchmaking and Dating Coaching business focused on an honest and hands on approach. Stefanie labels herself as “Chicago's Introductionista®” as she has over 15 years of experience in the matchmaking industry. Her work has been featured on various media such as: ABC7, NBC5, CBS2, WGN, FOX, The Chicago Tribune, The Chicago Sun Times, The HuffPost, and Refinery29. She holds a MBA in marketing and branding from Loyola University in addition to her BA from the University of Wisconsin-Madison.

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What do I wear on a first date?

For women, your number one priority should be your comfort! Plan an outfit with shoes that are comfortable. Don't feel like you have to go for a big sexy look. You don't want to feel like you're coming out of your top or your feet are hurting like crazy when you've walked two blocks. Everybody's styles are a little different in terms of what clothes or makeup they like to wear, so you do you! Just make sure not to be overdone with crazy amounts of makeup or jewelry.

Q&A Comments (77)

How do I touch my boyfriend?

This depends on where your boyfriend likes to be touched. However, if you're on a first date with a guy that you aren't an item with yet, a quick hug at the end of the date is usually considered appropriate.

How do I keep her interested between dates?

The most important thing is probably to make sure the initial dates go well. Women are very much looking at if you make an effort. Don't underestimate how important it is to be well-groomed, to have clean nails and hands, to dress a little more nicely than you would if you were just going out with buddies. Also, follow basic etiquette. Don't be on your phone when arrive, and don't sit and text during dates. Instead, be fully focused and paying attention to the person in front of you.

How do you touch a guy?

It depends on your relationship to the guy and what you each feel comfortable with. If you're on a first date, you could give him a quick hug to show that you're a little bit more than a friend. You could also sit a little closer to him and touch his hand a bit.

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Co-authored Articles (27)

22 Subtle Ways to Touch Him to Show Affection (or to Turn Him On)

Use physical contact to let a special guy know how you feel Touch is a great way to show a guy you care about him—or to drive him wild! If you want to make a guy fall for you, you have to know how to touch him the righ...

How to

Ask a Girl Out

''Earn yourself a date with these reader-approved tips'' You're so ready to go on a date with the girl you've been crushing on, but first you have to ask her out. How should you bring it up? What exactly should you say? ...

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Impress a Girl

Do you want to wow that certain girl? Though you can't control how she feels and make her fall in love with you, you can make yourself seem more desirable to her. Here are two methods for impressing a girl: first for a g...

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Impress a Girl when You First Meet

Impressing a girl when you meet her isn't the easiest thing in the world, but it can be done. Start by making yourself as impressive as you can with a nice outfit and practicing what you'll say. When you meet the girl, i...

How to Impress a Girl on WhatsApp

Capture her interest, charm her, and get her to text you backBe genuine, confident, and courteous, and you’re bound to make a good impression on any girl you chat with on WhatsApp. But what can you say to a girl on Wha...

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Invite a Girl to Your Place

So you like a girl, you’ve been on a few dates, and you've organized every outing to the last detail. But if you’re looking to get intimate with her, that won’t happen in the middle of a bar or restaurant—so you�...

How to Ask a Woman on a Date: Expert Tips & Mistakes to Avoid

Dating coaches explain how to ask her out (and have a great date)Asking a woman out on the first date can be exhilarating—and maybe slightly nerve-wrecking. You don’t know if you’ll be rejected or if she’ll accep...

21 First Date Tips for Men

Congrats on successfully charming someone into going on a date with you! That’s a huge accomplishment by itself, but now you’ve got to show them a great time to get past that first date—what’s a guy to do? With t...

How to

Get Your Crush (for Boys and Girls)

Having a crush can drive anyone crazy. It may be difficult to initiate conversation with your crush, but by building confidence and being yourself, you can win them over and start a relationship.

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Get Close to a Girl

Getting close to people is sometimes difficult. It is especially difficult when you want to get close to a girl for romantic reasons. As a result, you need to be very careful, move slowly, act naturally, and respect the ...

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Date in Middle School

Young romance. If you want to learn to negotiate the tricky dating world that is your local middle school, you can learn a few tricks and tips to make it go as smoothly as possible. You can learn how to ask someone out t...

How to

Be Confident in Your Looks

Having low self-esteem when it comes to your appearance can feel demoralizing and make it harder to focus on enjoying your life. Fortunately, there are things you can do to shut down your inner critic and start feeling m...

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Get a Boyfriend in a Week

We live in an age of immediacy: we want everything now and fast! This even includes romance. While this may not always lead to lasting "forever" love, you can definitely bag a boyfriend ''post haste'' and make him weak i...

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Impress a Girl in High School

If you’re popular in high school, impressing a girl may come easily; however, if you find it difficult, you can learn more about her, take steps to share in her interests, or make yourself more impressive from her pers...

How to

Tell Your Crush You Like Him

Admitting your feelings to a crush can be difficult. It takes a lot of courage to tell someone you like them, but it can be so rewarding once you do. By choosing the right time and place and being forward, your crush may...

How to

Take a Girl Home on the First Date

First dates are often the cause of both excitement and anxiety whether you’re inexperienced or a seasoned veteran of the dating world. At the end of a successful date, you may feel embarrassed to accompany her home or ...

How to

Impress a School Girl

Everyone knows the feeling of wanting to impress the person they like. But for many, the task of impressing the girl you like at school may seem daunting. You want her to like you, but you may not have any idea of where ...

How to

Set Boundaries when Dating

Setting boundaries in your relationship is an important part of making sure that you feel comfortable and confident as things get more serious. Communicating those boundaries doesn't have to be hard, and our guide can he...

How to

Build a Long Lasting Relationship

Everyone wants a butterflies-in-your-stomach still-in-love-50-years-later kind of love. But, based on the research of failed relationships and marriages, not many are willing to put in the work to accomplish this kind of...

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Talk About Your Dating History

Whether you’ve been seeing someone for a couple of weeks or a couple of years, discussing your past can be tricky. While it’s important to be honest, it’s also important to consider your new partner’s feelings. ...

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Stefanie Safran

Forum Comments (1)

Q&A Comments (77)

Co-authored Articles (27)