I Thought Planning My Engagement Session Would Be Easy!


It’s been fun sharing about my wedding planning experience! If you haven’t read all of the previous posts yet, here is a little recap for you thus far.

Week 1: How I Asked My Bridesmaids
Week 2: The Two Most Important Words of Wedding Planning
Week 3: Finding A Wedding Venue
Week 4: Choosing My Vendors

Today I’m getting more specifically into my engagement session planning. And woah. I didn’t realize how much effort this would take!

I thought this would be the easy part, considering I have so much experience planning engagement sessions. I mean, I do this for my clients all the time! But when it came time to start planning mine, well, it took me a good nine months to make it happen!


Here are a few reasons why I got overwhelmed:

1. I didn’t set a budget.
I only accounted for the session fee with my photographer, and then when it came time to plan for outfits, shoes, jewelry, etc., I wasn’t ready for that! Oops. Lesson learned.

2. I wanted to do everything.
I had so many ideas that I couldn’t narrow them all down to just one.

3. I was too set on being unique
Since I photograph and see engagement sessions all the time, I wanted mine to be unique. However, I focused so hard on being unique, I lost sight of what the session is really about – capturing this season in mine and Justin’s lives!

So here’s what helped me figure it all out…


1. My photographer Rachel and I started a secret Pinterest board.

Now let me just make something really clear that every bride should know! I  did not make a board of photos I wanted her to copy, or poses I wanted her to mimic exactly. This was a board to help us visually communicate what the vibe and mood would be. It helped me show her the wardrobe styling I was drawn to and the mood of the images I liked. What also helped is that, since Justin and I have such a huge height difference, I was able to pin some poses I loved. These weren’t poses for Rachel to copy, but they were ideas for her to draw from and make her own!

2. We chose two different looks

The major problem I had with making a decision, was that Justin and I are completely opposite in so many ways, it’s hard for us to agree on style! The fact that we are so opposite is what works for us. We are two extremes that balance each other, and that is what makes us so great together! Justin is laid back and I’m very high-production, so we did a look to represent him and a look to represent myselg.

3. Rachel helped me refocus on what mattered

I was so focused on doing something different, that I forgot what the engagement session is all about – capturing Justin and I in this amazing season of engagement. I’m thankful for my wedding photographer who could keep me on track. I stepped away from Pinterest ideas and went back to what represented Justin and I in this season. What brought us together was our mutual love for music, so I knew we had to incorporate this into our session. We are also major movie goers, so we wanted to subtly incorporate some feel of Hollywood.

4. I decided to expand my budget for things I valued

Wardrobe is a huge aspect of the final product when it comes to a photoshoot. I decided to budget for the shoot beyond just my photographer fee and I am so happy I did! One of my best investments was my gold, sparkly Rent The Runway dress. And now I feel like everyone needs to know about them! If you want to setup a free account and start shopping for amazing rental dresses online, email me before you sign up (contact@jennaphoto.com) and I will send you a link to get a coupon!


So here’s a breakdown of our two looks and why we chose them.

Look One – Casual & Authentic

This one was Justin-inspired. Simple, authentic, and down-to-earth. A typical day off for us during this time in our life would include a mini-road trip to somewhere about an hour away, his acoustic guitar, and an adventurous go-with-the-flow type of day. We wanted to capture this aspect of our relationship.

Even though we wanted casual, the wardrobe still affects the image quality, so we focused more on color. Justin loves black and gray, so we chose his outfit first, and I planned mine around his. We chose something already hanging in his closet, and I wore jeans with a peplum top that included a mix of black and florals to tie in with the environment. Though I typically wouldn’t wear heels out on our day-dates, I added these to my look, because heels are more flattering to posture in photos. This definitely helped balance out the fact that I was wearing jeans (I typically recommend dresses for an engagement shoot!).



Look Two – Fancy & Hollywood Inspired

Our whole wedding was mostly classic, yet subtly themed around music & movies. Since our wedding details were so simplistic, I wanted our engagement photographs to represent more of a theme. I started with the mood I wanted to create. From there I chose a location. I was inspired by beautiful architecture and soft whites for our setting. Despite Balboa Park being a popular place for engagement photos, I fell in love with the theatre there from the moment Justin and I saw it a couple years back, and I’m happy we went with it!


After choosing a location, we started to focus on wardrobe. I found this gold sparkly gown on Rent The Runway and I knew Justin needed something sharp and dapper to coordinate. We went to my friends at Friar Tux who went as far as helping us style Justin’s look! Eric, the district manager, was on board with our Old Hollywood, Music & Movies inspiration, and he mentioned that some men used to change into a white dinner jacket for the evening. We decided to give Justin another look for our walk downtown at night, and it was lovely!


I knew I wanted to have professional makeup for the session; it makes such a difference! I scheduled my wedding makeup trial with Raeleen Babbel (I just didn’t tell Justin I was doing the same thing for the wedding!). It was great to be able to get his opinion on my wedding makeup without actually knowing it was going to be used again. 😉

I had scheduled a cut and color for the week prior, so it would look a bit more natural for the session. My close friend Yuliza helped me curl it on the day of, and I’m so thankful for her! She has a natural talent for just about everything.

Justin had his hair cut by Erin Heck who also came and styled his hair for the wedding!


Carla Kayes, my wedding florist, made a sweet mini-engagement bouquet for the session to add some prettiness, and it was perfect!


We also decided to bring in another guitar for this part of the session, and none better than Justin’s black and white Schecter! I love his musician side.


Yep, I’m really that teeny. And Justin is 6’2″.




My sweet calligrapher friend Kristin of Phoenix Feathers Calligraphy created this beautiful sign for us! The quote comes from Justin’s father’s speech at our engagement party who is a huge fan of Shakespeare (and we are a huge fan of him). He said a few words the night Justin proposed and planned a surprise engagement party for us. In closing, this line reminded him of us:

“The very instant I saw you did my heart fly…”
-Shakespeare, The Tempest







After leaving Balboa Park, we ended the night with a walk in Downtown San Diego! Justin switched into his white evening jacket and looked as handsome as ever.



And this is one of my favorite poses of the evening! It’s so “us.”


Though it took me nine months to plan this (or should I say stall planning this!), I am so happy with the way it all turned out. I have so many people to thank, so here it goes!

Photography: Rachel Jay (and Jessica Van!) of France Photographers
Mini Bouquet: Carla Kayes Floral Design
Calligraphy: Phoenix Feathers Calligraphy
My Hair: Yuliza Castillo
Justin’s Hair: Erin Heck
My Makeup: Raeleen Babbel
Gold Sequin Gown: Rent The Runway
Tuxedos: Friar Tux
Locations: Balboa Park and Downtown San Diego
And last but certainly not least, my cousin Janae who helped me get ready for the day and picked up the flowers for us!

Want to catch up on the rest of the #jennajosephbridalexperience blog series?! Follow the links below!

Week 1: How I Asked My Bridesmaids
Week 2: The Two Most Important Words of Wedding Planning
Week 3: Finding A Wedding Venue
Week 4: Choosing My Vendors

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