Let’s start with the biggest misconception about engagement sessions: they’re awkward.
I hear it all the time: “We’re so bad at photos,” “This is going to be weird,” or my personal favorite, “We’re not professional models.”
Here’s the good news: engagement sessions in and around Milwaukee are actually fun. Like, genuinely enjoyable. No stiff posing, no pretending to be someone you’re not, and absolutely no pressure to turn into professional models.
Think of your engagement session as a warm-up - a chance to get comfortable, laugh a little, and walk away with photos that actually feel like you.
Milwaukee Is an Underrated Engagement Session Goldmine
Milwaukee quietly has everything.
In one city, you get:
Lake Michigan views and breezy shorelines
Urban streets, brick buildings, and industrial textures
Cozy neighborhoods and hidden pockets of greenery
A mix of modern, historic, and slightly gritty backdrops
Whether you’re drawn to the lakefront, downtown vibes, or something more low-key, Milwaukee offers variety without having to drive hours between locations.
No, You Don’t Have to “Know How to Pose”
This is important, especially if you’re the type who feels awkward in front of the camera.
You don’t need to:
Practice smiling in the mirror
Memorize poses from Pinterest
Feel "on" the entire time
Engagement sessions work best when you’re simply interacting - walking, talking, laughing, and occasionally forgetting the camera exists. My job is to guide you just enough to keep things natural, flattering, and comfortable, not to turn you into someone you’re not.
Awkward Moments are Documentary Gold
If you’re worried about feeling awkward during your engagement session, here’s the secret: preparation has nothing to do with practicing poses. The best way to feel comfortable is to show up knowing you don’t need to perform. Wear comfortable outfits (not something you’re constantly adjusting), plan to move a little - walking, leaning in, laughing - and trust that a good photographer will guide you without over-directing. I’ll give you prompts, not poses, and plenty of space to be yourselves. Awkward moments happen, and honestly? Those usually turn into the best photos.
Choosing an Engagement Session Location (Without Overthinking It)
Here’s a little secret: the best engagement session locations aren’t always the most popular ones.
Instead of asking, “Where do people usually take photos?” try asking:
Where do we like spending time together?
Do we want something calm or energetic?
Are we more lakefront stroll or city street wander?
Milwaukee engagement sessions are at their best when the location fits your personality, not just the trend of the moment.
What to Wear (A Gentle Reminder)
Comfort > perfection. Always.
Wear something that:
Feels like you
Allows you to move easily
Makes you feel confident, not distracted
Neutral tones photograph beautifully around Milwaukee’s textures, but personality is always welcome. Shoes you can walk in? Highly encouraged. If you still want some high-class, dramatic outfits, definitely still bring those (hello main character vibes), but make sure you still have outfits that show off who you are on a day-to-day basis too.
Engagement Sessions Are Practice for Your Wedding Day
This is one of the biggest benefits couples don’t realize. Working with your photographer even just once before the big day will be such a game-changer for your wedding portraits.
Your engagement session helps you:
Get comfortable being photographed
Learn how I’ll guide you on the wedding day
Shake off nerves before the big day
Build trust (which shows up in your photos)
By the time your wedding rolls around, photos feel familiar and fun, not intimidating or awkward.
One Final Note: Come As You Are
Engagement sessions aren’t about perfection. They’re about connection. Milwaukee offers the perfect backdrop for photos that feel relaxed, honest, and fun, especially when you show up as yourselves.
Need a photographer who can help guide you through all that initial awkwardness? Connect with me by clicking here.
