My Life Is A Ben Stiller Movie + What To Wear To Meet The Parents

After exiting a long-term relationship, and living a less than exciting single life for the two years to follow. Re-entering an actual relationship can be daunting. The many relationship milestones that I had already reached in my previous relationship went right out the window.

“What do I say? What did he mean?”

“Should I text him? No. When the f*ck is he going to call?!”

“What do I do with my hands?” (wait, what!?)

And most importantly, “What do I wear?”

From the first date to walking down the isle – your dating life is FILLED with fashion choices. These simple choices have the power to make or break your relationship. Oh, you think I’m dramatic? Think again. Try wearing some tragic outfit on the first date and see how far that goes.

I’ve managed to dress my way into the “meet the parents” stage of my relationship.

If you are a member of my VIP mailing list (get on the list and score a free gift here), then you know that I went out of town a few weeks ago. An epic 6-day trip that involved not only meeting HIS family, but him meeting MY family – to be exact.

Talk about a real life Ben Stiller movie.

Before I jump into the story, I’ll start by saying this I am a TOTAL introvert. So wowing people with my personality doesn’t come until much later. Meeting new people kind of makes me want to die. So it is paramount that I get the outfit right. Style is my way of communicating.

Now I’m sure you’ve read a ton of “what to wear to meet the parents” posts in your internet travels, but what all of those posts are lacking are the specifics. What do I mean? I mean all parents aren’t created equal. There are certain elements you need to consider before picking out your outfit.

Ask Yourself

1.) Where are you meeting them? At their home, at your home, at a fancy restaurant, at Starbucks, in a shack in the middle of the woods … You have to make sure you are dressed for the setting, so you don’t stick out that a sore thumb.

2.) What are they like? Do you research. Does your man come from money or a blue-collar family? Is his family super serious where politics is the topic of discussion at the dinner table? Or is talking about who got booted off of American Idol the subject matter?

3.) Who will be there? Is it just the parents or are the grandparents going to be present? Small children? Trust me, all of this makes a huge difference when it comes to deciding what to wear.

Alright, now back to my trip. All of the questions that I broke down above are questions I asked myself before getting dressed.

The Meeting

Our first meeting was a super-casual brunch setting. Oh, just a small intimate breakfast for FIFTEEN people! Did I mention I am terrified of people?? I knew I was meeting a diverse range of ages (4-year old cousins, all the way up to the grandparents), and I also knew that his family was pretty low-key. That meant shelving the “fancy Lauren” attire, swapping out the heels for boots, and wearing something that said, “Hey Grandma, I’m totally cool and not at all a deviant.” Oh and while totally staying true to myself and my personal style. Easy.

Not really.

Even as a stylist, I had to edit my outfit quite a few times before walking out the door.

The Outfit

Attempt #1- Skinny jeans, tee shirt, leather jacket, boots, statement earrings.

While I felt very “me” I also knew that the leather jacket paired with the skinny jeans could come off as a little “abrasive”. I knew I wasn’t going to get in a lot of talking because a.) scary and b.) table for fifteen. The earrings were fun and showed personality but were an accessory that some nice folks from the Midwest wouldn’t understand.

Attempt #2- Flared jeans, military style jacket, tank top underneath, boots, and a necklace gifted from the man himself

I looked hot. A little too hot and a little too dressed up for the restaurant. Next! Decided to save that look for the “meet my best friend and her family” dinner. Yeah, that dinner happened during this trip too.

Attempt #3 (the winner)- Burgundy velvet flares, navy blue cashmere sweater, wedge boots, nameplate necklace from my man

This outfit, admittedly, was the least Lauren out of them all (except for the necklace). However I felt stylish enough to show that I work in fashion, covered up enough to not scare grandma, appropriate for the restaurant (OK maybe still a touch overdressed), and comfortable enough to go where the day might take us.

When it was time for him to meet my parents, I obviously didn’t give a damn about what I had on. LOL! My family already knows me. However, immediately after meeting my parents, we headed down to Washington DC for a movie screening. So we dolled ourselves up a bit. My parents were impressed.

So … one suitcase full of clothes and two nervous breakdowns later, we made it through the trip without saying, “Bye, Felicia!” to the relationship. What didn’t kill us made us stronger. I met his family, and he met mine. All parties seemed to get along just fine. I can check one style/relationship milestone off the list. I wonder what’s next??