8 Awkward Dating Situations (And How To Get Out of Them)

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Premiering today, That Awkward Moment starring Zac Efron, Miles Teller and Michael B. Jordan shows three friends experiencing dating in all of its glory head-on, with plenty shenanigans that many of us can relate to. Ultimately we’re all just winging it, learning on the fly and having unique dating experiences full of so, so many awkward moments.

1. Deciding who is paying for what on dates.

There’s no clear answer to this one, which can lead to confusion when the check arrives. Does the person who initiated the date pay? Does the person who sorrowfully pulls out their wallet the slowest get off the hook? Do you split the bill down the middle? What if one person ate more than the other? I don’t know about you, but 50/50 doesn’t seem fair when you had water instead of strawberry lemonade and no extra side of ranch. This can be a dilemma filled with uncertainty and discomfort if not addressed beforehand.

How to get out of this: If you plan on paying, don’t hesitate. Just grab the bill and handle business without asking questions, making statements or dilly-dallying.  If you don’t want to pay the full thing or are uncertain how it’ll be handled, you’re at the mercy of the other person’s reaction, so buckle up and remain seated for what could be a bumpy, turbulence filled ride. Your best bet is to not get flustered and play it cool when asked how you’ll be paying, or just like, talk about it with your date in advance.

2. Explaining to your friends that you’re going to be involved with someone else.

Be prepared to spread yourself thin because you’ve got friends who want your tender love & care and will request your presence, plus a separate person who you’re obligated to spend a significant portion of your time with.

How to get out of this: Sit friends down and speak in a compassionate tone as if you’re about to tell a child that Santa doesn’t exist. Explain how much you care about them and reiterate that’s it’s not their fault and they did nothing wrong, but you’ve been dating someone who will now be occupying a chunk of your time. Reassure them that very little will change (whether you believe it or not) for the sake of this.

3. Ranting about a topic only to find out shortly thereafter that they feel completely the opposite.

When this happens there are different levels of awkward that can be reached. It’s something like this;

Playfully awkward: I hate [FILL IN SPORTS TEAM HERE]. Oh they’re you’re favorite?! *Lighthearted banter*”

Somewhat awkward:
Cheerleading isn’t even a sport, I don’t get the big deal about it. Oh, you were a cheerleader for 10 years? Of course you were…”

Incredibly awkward: I can’t stand bicyclists; those people think they own the road! Oh, was he? Did he survive? Wow, I see… Well I’m sorry to hear that, rest in peace to your Grandpa Charlie.

How to get out of this: Try to hold conversations on topics you can speak positively of and steer clear of potentially touchy subjects that might result in you eating your words.

4. Use of the word ‘love’ before you’re ready for it.

Some people drop the L-bomb on you when you’re not ready to drop it back, and that can be a terrifying experience. Love can be a great thing but when it isn’t a two way street things get tricky. Think of it like this: ice cream is delicious & amazing, but if you’re lactose intolerant it’s not so wonderful to you. In fact, it’s completely petrifying.

How to get out of this:
DON’T SAY IT BACK IF YOU DON’T ACTUALLY MEAN IT. Feelings may get hurt and some awkward may take place, but love is a powerful word that has no business being thrown around where it isn’t reciprocated.

5. Deciding on the appropriate way to say goodbye at the end of the first few dates.

Hug? Handshake? Kiss? Peck or French? Do I lean in? Are you going to lean in? Are you inviting me inside or do I have to drop a hint if I’d like to further the evening? So many thoughts and possibilities which can lead to you awkwardly leaning in for a hug and landing chest first on their extended hand. It’s disastrous, it’s humiliating and when there are no clear indicators of what’s appropriate or approved of, the odds of you and your date not being on the same page are scarily high.

How to get out of this: Don’t be the initiator of anything unless you’re fairly certain they want your warm embrace or lip-on-lip contact.

6. Interaction after the first time hooking up.

When dating there are many layers of the connection, but broadly speaking there’s pre-hookup and post-hookup. After the hookup has taken place, the interaction immediately following can reek of awkwardness. Some might become shyer, others may become too comfortable, but a change in the vibe after hooking up for the first time is par for the course.

How to get out of this: Unless you’re willing to postpone hooking up there’s no real way out. The more you embrace the temporary awkward and face it head on the faster it’ll fade out.

7. Running into people who know you well.

In the early stages of dating folks tend to be an exaggeratedly splendid version of their usual selves. On one side we have Regular You, and on the other it’s Dating You. When you run into a person familiar with Regular You while you’re with the person who only knows Dating You, it can be scary to see two worlds cross. It’s like, oh geez, please don’t say something to spoil this façade that I’ve worked so carefully to enforce.

How to get out of this:
Control the conversation. This three-step approach works like a charm:

  1. Hey, [PERSON WHO KNOWS YOU’S NAME] this is [YOUR DATE’S NAME].
  2. What are you doing here?
  3. Well it was great to see you, bye.

8. Defining the relationship.

Labeling what you and this person are is so scary/difficult/nerve-racking. Are we talking? Are we best friends? Are we special pals? Are you my boyfriend/girlfriend? Are we going steady? Is it the 1950s? No, then why use the term going steady? So many questions with no solid answers.

How to get out of this: Talk in circles, change the subject, deflect with statements like “Why can’t we just be whatever and as long as we’re happy not worry about conforming to society’s labels.” Just know that you may temporarily escape but this is an inevitable discussion that’ll eventually lead to a gigantic step being taken, whether it be forward or back. TC mark

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