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6 Ways To Perfect Your Status As The Ultimate Third Wheel


Third-wheeling can be an incredibly awkward experience. It can also be an extremely empowering one. I find it fun to spend time with my friends, my siblings and their significant others. Often times, I become friends with these people.

Yes, things can get awkward. But don't run away. You have to work through this awkwardness. No pain, no gain.

Third-wheel relationships are like fine wine: They get better with age. The more comfortable you become as the third wheel, the better. Here's how my experience third-wheeling my sister and her boyfriend's romantic weekend to Woodstock helped show me how to become the perfect third wheel:

1. Establish your position.

First, you must establish your position. If you show you're uncomfortable, or if you make the fact that you are the third wheel too obvious, you are destined for failure.

Before the trip, I had already firmly established my place as the third wheel. I became best friends with my sister's boyfriend. We would all do dinner together. We would even work out together. I felt like one of the gang.

When we arrived in Woodstock, I plopped my sorry ass in a rocking chair. I established my dominance from the get-go.

I'm so comfortable with my sister's boyfriend. We can cuddle without it being weird. The first evening in Woodstock, we cuddled on the couch. It's a true bromance.

I established my third wheel position, and firmly.

2. Infiltrate their everyday activities.

To create a good camaraderie and relationship with the couple, do normal, everyday things with the two of them. Begin to infiltrate their activities.

A great example of this is buying groceries. This is the classic activity for any Manhattan couple on a Sunday afternoon. On the evening of our arrival in Woodstock, we were without food or sustenance. Therefore, we headed to the grocery store.

As it was Woodstock, we couldn't find a regular grocery store like Whole Foods or Trader Joe's. But we did find a cute organic grocer.

I was like a kid in a candy store. Every time I put an item in the cart, Gigi would take it out. (Thanks a lot, sis.)

Of course, a fight started over the kind of food we should buy. But once the crisis had been handled, we bought our food and moved on to Rite Aid, where we bought more junk food than a group of 17-year-old boys coming off a high.

The lady behind us in line said, “I guess what happens in Woodstock, stays in Woodstock.” Yeah, it does.

3. Try not to make things awkward.

Do not – I repeat, do not – make things awkward. (Well, maybe you can a little. Hehe.)

While we were in Woodstock, I made it a point to take selfies with the happy couple whenever they made things awkward for me. A few examples of this is when they started making out on the couch while I was in the room, or when they started full on sucking face on the side of the mountain during our afternoon hike.

In an effort to make things less awkward, I made light of it all. Crisis averted.

4. Go on a date with them.

This one is super fun. Go on dates with them: dinner, a movie, Disney World, Six Flags, the flea market. Maybe even a combination?

I did this in Woodstock. We decided to take a quick drive through the idyllic town. I think Woodstock must have been the inspiration behind Stars Hollow in "Gilmore Girls."

We went to the most adorable little movie theatre. It gave out fair tickets instead of regular movie tickets. I almost couldn't handle how cute it was.

We saw “Room,” which is a film about a young girl who was abducted. The story is about her raising her son in a single room. It was beautiful, touching and equally horrifying. So basically, it was the perfect romantic movie date for three.

As we left the theatre, tears still in our eyes, I asked my sister's boyfriend if he had liked movie. He was like, “Not really.” Glad the message resonated. Date number one was a success.

5. Know when to push the boundaries.

A great third wheel knows when it's appropriate to push boundaries. On our last night in Woodstock, we all watched "The X-Files" reunion. It's an excellent, wonderful sci-fi series that recently returned to Fox after over a decade. It's a classic, but it's also scary.

Once we had finished a few episodes, it was time for bed. But alas, I got scared. I didn't want to sleep downstairs, alone in an exposed cabin in the woods. Sounds like a Hollywood murder plot, doesn't it?

So, I asked my sister and her boyfriend if I could sleep on the couch in their room. I knew just when to push the boundaries. Romance over. I was sharing their room.

They farted to get back at me. Charming.

6. Own the third wheel title, but give them space.

As any trained third wheel knows, you must know when to give the couple their space. You mustn't smother them.

I let my sister and her boyfriend have some space during the weekend. They took a romantic bath  – no, I was not involved – and shared intimate moments together, despite the time when I decided to sleep with them. (Sorry. I got scared.)

In the end, you can't win 'em all. The professional third wheel knows when it's appropriate (and even necessary) to back off.

So, there you have it, everybody: the step-by-step guide to becoming a professional third wheel. Seriously, I highly recommend that you all go out and try this right now.

Don't walk. Run.

I'm glad to say I survived the romantic weekend, and I'm a better person for it. Third-wheeling f*cking rocks.

I was excited to try again, so I asked them if I could join them for their romantic Valentine's weekend. They responded, “Go be with your boyfriend.” I guess lightning really doesn't strike twice.