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Halloween can be tricky, no pun intended, when you just started dating someone new. Your plan was to go out with your friends, but the new hottie is dropping hints about spending Halloween together. What do you do?

Going out with friends is a safe bet. The obvious reasons for going out with him are:
1. You want to spend more time with him
2. You’ve had great one-on-one interactions, time to explore
3. You want the exchange of attention and affection
4. You love Halloween and it would be great to have a date
5. You’ll get to see a different side of him and him of you (costume choice is revealing)
6. Last, but not least,  you have one sexy costume this year!

He’s probably thinking the same…except maybe not the last thought (Zoro would be sexy to me especially if hes’ a techie by day. I love the extremes. I was Elvira last year and I’m a bit of a geek myself. Back to topic, least I digress…)

You could always have your new guy join you and your friends for Halloween…that could be the best of both worlds.

However, there was the one time I was dating George for two months and we decided to go to my girlfriend’s Halloween house party. I knew everyone, he knew only me. He was an introvert (dressed as a Spiderman) and didn’t feel comfortable socializing on his own. I wanted to make sure he felt comfortable so I spent most of the evening introducing him to my friends. The evening was not nearly as fun as I had remembered previous years attending the same party without a date.

The flip side, I had a great time attending a Halloween party (and hosting one for that matter) with my boyfriend of a year who knew all my friends and was secure in our relationship. Being secure helps when 98% of the women are wearing sexy costumes (’tis the season to look vampy) and he can’t help, but be distracted.

When you have so many challenges as it is in a budding relationship, perhaps spending Halloween together is not the best choice?

According to Joe Berkowitz, Halloween is “Doomsday for a New Relationship.”

The ones who’ve been together long enough to have sifted through and itemized each other’s garbagey baggage are probably in for a killer time. With a new relationship, though, it’s a different story. When couples are still finding their footing, neither person really knows who the other one is. If you’ve only started dating recently, Halloween is the moment when the masks come off. Boo.

Joe reminds us how stressful the planning can be for Halloween, such as the costume decision.

The anti-costume person might see her opposite as immature and embarrassing; someone who will go chasing waterfalls instead of rivers and lakes, etc. If you’re pro-costume, though, you may think your counterpart is either too cool for school or prematurely wizened into retired homebody status…

Beware if you have a “fly by the seat of your pants” attitude…

So the bad news is that if you’re in a new relationship and you just sort of let ‘whatever’ happen on Halloween night, you might wake up on the first of November facing the beginning of the end. The good news is that this outcome is by no means predetermined! When you plan whatever you can plan and bring a laid back attitude to the unforeseeable, the odds are weighted heavily in your favor. Halloween can be a stress test, but the best relationships gain strength from adversity.

I would recommend reading the entire blog. Joe’s examples are a real treat!

As for what I would recommend, my vote would be to spend Halloween with friends and wait until your first anniversary to spend Halloween together. And, don’t try to squeeze each other in for an end of night meeting and no drunk texting.

HAPPY HALLOWEEN!