Finally, A Dating Profile That Gets You Dates in Chicago

Stand out in Chicago’s dating scene with real, professional photos that highlight your personality and authentic story. Forget generic headshots, showcase your confidence and attract women who value the real you.
More Matches
Better Conversations
Real Dates
100+ 5-Star Transformations
Before
after

From YouTube's Go-To Channel for Dating Advice…
...to your personal dating photoshoot

You may know us from our content breaking down Tinder, dating, and men's lifestyle. We show men how to navigate the modern dating world, and now we’re here to apply that same winning strategy to your photos.

Think of this as the ultimate advantage: your photoshoot is directed by the same experts who are setting the standard for men's dating advice online. We don't guess what works, we know.
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The Attraction Algorithm Photoshoot

A great dating profile isn't a lucky accident. It's a carefully crafted portfolio where every image serves a specific function. We don’t just take pictures; we execute a 7-shot formula designed to showcase the key pillars of male attractiveness.


Our Battle-Tested 3-Step Process for Better Dates

The Strategy Session

We start with a clear and simple planning call. We'll discuss your goals, define your personal style, and create an easy-to-follow game plan for your shoot, ensuring you arrive confident and prepared.

The Guided Photoshoot

This is a relaxed, guided experience designed to capture you at your natural best. We'll lead you through a variety of proven shots, making simple adjustments to ensure you look confident, approachable, and authentic.

The Profile Launch

Our service doesn't end after the camera clicks. We deliver your finished photos and then personally help you select the strongest lineup. We'll even help you craft your bio and prompts to create a complete, optimized profile that's ready to attract great matches from day one.
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Why Our System Outperforms a Standard Chicago Photoshoot

Predictable ROI for Your Time

Our system is designed to save you countless hours of swiping, giving you more time to actually enjoy the city... from drinks in the West Loop to weekends on the lake. It's the smartest investment you can make in your dating life.

A Formula Built for Chicago

Our data-backed, 7-shot playbook is designed to show your full range as a Chicagoan. We capture the polished professional and the relaxed weekend local, proving you have depth beyond a LinkedIn headshot. It's a complete narrative built to resonate with the smart, discerning women you actually want to meet.

Direction That Feels Authentic

We skip the stiff, awkward poses and use specific, technical cues to capture your genuine personality. You'll look confident and grounded, not arrogant or try-hard. It’s the difference between looking like you belong and looking like you're trying to.

An Unfair Algorithm Advantage

The Chicago dating pool is massive. To get noticed, you have to play smarter. We know the inner workings of Hinge, Tinder, Bumble, and more, and our process is designed to give the algorithms the visual data they favor. This pushes your profile to the front of the line, ensuring you get seen by the right women.

A Look Inside the Wingman Plus Dating Photography Experience

We take care of literally everything so you can 10x your matches and meet your next girlfriend FAST.
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Before
after

Level Up Your Dating Game Just Like Cody Did

“Since my WingMan Plus photoshoot, my dating life has been fantastic. I’ve had more numbers and more everything than my whole life. I even lost my virginity and have a date lined up today. My new photos are night and day compared to before, they actually show what I look like and boosted my confidence. Now I can talk to just about anybody, and it’s been awesome.”
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Real Results with Our Dating Profile Photography

Alec, 29

I went from zero dates to TOO MANY dates in 3 months

Aspen, 27

I Got 40 Matches in the First 2 Days

Sean, 26

Within 5 Days of the Profile Makeover, I had 5 Different Dates

Cody, 32

Built a roster of 5 women in the first 30 days.

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The Science Behind Your Standout Chicago Dating Profile

The Narrative Anchor
45%
Function: To spark curiosity and provide conversation starters.

The Data: Profiles with contextual, story-driven photos receive up to 70% more opening messages. This shot establishes you as a man with passions and a life beyond the frame.
The Authenticity Signal
35%
Function: To build trust and create an emotional connection.

The Data: Women subconsciously assess trustworthiness in milliseconds. We use specific direction to capture genuine micro-expressions of ease and confidence, bypassing the viewer's "fake profile" filter.
The High-Value Indicator
15%
Function: To show competence and high standards.

The Data: Image quality is a direct signal of personal standards. A professionally lit and composed shot communicates that you are a man who invests in himself and doesn’t settle for mediocrity.
The "Genetic Fit" Factor
5%
Function: To satisfy the brain’s primal checklist.

The Data: While classic "looks" are a small part of the equation, they matter. We use expert angles and lighting not to make you look like a model, but to present the most attractive, authentic version of your unique features.
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This Is for You If...

You believe in efficient systems, not blind luck.
You want a predictable ROI on your time, energy, and money.
You’re an expert in your field and prefer to work with proven experts in theirs.
You're tired of guessing and ready for a definitive solution.

Get Your Ultimate Photoshoot Prep Guide (Yes, It's Free!)

Learn why 90% of dating photoshoots fail. It’s all in the details. Get our free guide for the secrets that get more matches.

Frequently Asked Questions

How long until my optimized assets are ready?

Your complete, edited image gallery will be delivered for deployment within 5−7 business days.

Is this really a "formula," or just good photography?

It's both. Great photography is the tool, but the formula is the blueprint. 

A great chef can cook anything, but they follow a specific recipe to get a consistent, perfect result. We do the same for your profile.

I hate having my picture taken and I'm awkward on camera. Can you really help me?

Yes. In fact, about 99% of our clients say this exact thing. 

"Being photogenic" isn't a trait you're born with; it's a result of comfort and expert guidance. Our entire system is designed for men who aren't professional models. We use specific, technical direction, not vague commands like "act natural" to make you feel comfortable and look your absolute best. We guarantee you won't feel awkward.

This is a big investment. What if it doesn't "work" for me?

We get it, and the best way we can answer that is by asking you to look at our reviews. You’ll see dozens of success stories from real men who started in the exact same place you are now.

Our definition of "working" is giving you the absolute best possible tool to succeed. We can't force a connection, but we can build you a profile that is strategically designed to attract the right people and give you the highest possible probability of success. Just like it did for them.

I’m over 40. Is this service still for me?

yes, absolutely. We adapt the entire process for our more established clients. 

The goal shifts from showcasing potential to showcasing a rich, established life. 

We focus on locations, wardrobe, and editing styles that highlight maturity, sophistication, and confidence. 

We’ll make you look like a man at the top of his game, not someone trying to compete with guys in their 20s.

Where do the shoots take place in Chicago?

We choose locations based on the unique story we're telling for you. 

We map this out during our strategy call, but common routes include a mix of neighborhoods like the West Loop for an urban-cool vibe, Lincoln Park for natural settings, and the Gold Coast for a more polished, architectural feel. We always avoid the main tourist traps.

Can I bring my pet?

Yes, absolutely! We love incorporating pets into shoots as they are a fantastic way to showcase your personality. 

The most important step is to bring it up during our planning call. This allows us to discuss the specifics of your pet (whether it's a dog, cat, or something more unique) and ensure we choose a location that is both safe for them and suitable for the shoot.

I have a specific hobby (e.g., sailing on Lake Michigan, bouldering, playing guitar). Can we build the shoot around that?

Yes, definitely. In fact, we encourage it. Incorporating your genuine hobbies is the single best way to create a profile that is authentic and sparks conversations. 

Tell us all about your passions on our strategy call, and we can design the entire shoot around that activity, ensuring we capture you in your element.

What happens if there's bad weather on our scheduled shoot day?

We monitor the forecast closely leading up to your shoot. If it calls for heavy rain or other prohibitive conditions, we will connect with you to reschedule for the next available date that works for both of us. There is no fee for weather-related rescheduling.

How do I book my shoot?

Click here and fill out our quick application form.

We’ll follow up within 24 hours to schedule your planning call.

Ask Us Anything

Your confidence in our process is our top priority. For any questions not covered in our FAQ, please don't hesitate to ask.
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