When Dating Gets Awkward! How To Get Out Of These 9 Sticky Situations

August 28, 2013  |  
1 of 10


Remember that time you thought it was a date but it wasn’t? Or how about avoiding that good night kiss you didn’t want to have? Or that Saturday night all of your ex boyfriends and new love interests were doing the wobble together? Yeaaaaa. Dating is fun, exciting, and even an occasional headache. But how do you handle it when dating gets…awkward?

Running into the ex that wants you back

There’s always one ex that just doesn’t get it. The relationship has BEEN over but he/she is still waiting around hoping you’ll change your mind. Then one day you run into them while out on a new date. And we all know how petty this particular type of ex can be. What an uncomfortable situation! How to handle it: If your ex speaks to you do not duck under the table or throw a wine glass. Keep the conversation short and don’t answer any questions. A simple hello and keep it moving. Most of all don’t let your ex become the topic of conversation on your date. It will be natural for your new date, having seen your ex now live and in person, to want to ask questions. Move the conversation away from the past and on to your future to make this less awkward.

Too many dates at one party

Remember the episode of “Moesha” when she dated several guys and they all showed up to her birthday party? Maybe your life is an episode of “Moesha” too. When you date within your friendship circle or a small peer group, it’s likely that men you are currently dating or have dated will all be at the same party sharing a snack at the kitchen counter. How to handle it: Do not leave the party. Do not hide in the bathroom with one of your friends planning an escape route. You are single and single people date. There’s nothing to be ashamed of here. Instead, go out and in full confidence, speak to everyone and play it cool again. There’s not an issue unless you make it one. Hopefully the people you’ve dated in the room can all coexist without making you the topic of conversation.  

Texting the wrong person

Why, in heaven’s name, in 2013 is there no way to unsend a text? I can’t sign up for a newsletter about cute puppies online without confirming my identity and blood type. Why can’t they make it so you have to confirm sending a lusty or romantic text before you actually press send? Sending the wrong person a text meant for someone else just makes you want to throw your phone out the window. How to handle it: Pretending that it was a joke or that someone was playing on your phone is not the way to go. More than likely the person won’t believe you and now you seem slightly immature. Just be honest if asked about it. There may be some hurt feelings on the other end but if you’ve been honest that you are dating multiple people then this shouldn’t be a problem. If you haven’t been honest…well…just go to sleep and hope all is forgiven in the morning.  

Canceling on one date and then seeing him/her while you are out

Sometimes we agree to dates and later cancel. Maybe you canceled because you had a better date option, wanted to spend time with your girls, or just wanted some alone time. Whatever the reason, you canceled on your date with a lame excuse like you need to wash your hair or catch up on “Scandal.” Then, to your surprise, you run into the person while you are out. How to handle it: You’ve got to be honest. It won’t go well. As my mother says, you made your bed hard now sleep in it. There’s no way to handle this awkward situation without looking like a jerk. If the person you canceled on confronts you, just be honest about the situation and why you didn’t want to go and gave an excuse. Maybe you’ll be able to salvage the relationship or let it go amicably.  

The goodnight kiss you don’t want to have

Not all dates send romantic fireworks throughout your body. Some are lackluster and destined for friendzone purgatory. The night is coming to a close and you can feel the tension rising as your date, who is clearly in love and missing all of your body language, prepares to go for the good night kiss. How to handle it: Sneeze. Now hear me out, nothing breaks a romantic mood more than allergies. If you feel the person preparing to go for the kiss and you don’t want to just put your hand in their face and say “absolutely not,” create a distraction to break the tension. Sneeze. Drop something. Fall down. Do anything to break the moment so you can hurry off to your car or train with a simple wave and good night.

The Catfish

The popular TV show, Catfish, makes it seem like dating online is all smoke and mirrors. Unfortunately, the show isn’t fiction so this is a real scenario. There’s nothing more awkward than sitting down for a date with an online love interest and a totally different person than you were expecting sits down in front of you. How to handle it: If you aren’t too pissed, and the person is nice, you can make it through the date. You can address any feelings you have about being lied to or deceived, but try not to seem super shallow and get up immediately because a boogawolf sat down in front of you. Keep it friendly and keep it lighthearted. You never know if you’ll make a new friend or even learn to like the person for who they actually are.  

Your date dated one of your friends

Social media usually makes this awkward dating situation less common because you can get a good idea of someone’s social network with just a few clicks. However, occasionally you go out on a few dates only to discover this person is actually someone that dated your friend before. How to handle it: Dig deep with the date and with your friend to find out the nature of the relationship. You’ll need to get perspectives from both parties, evaluate your feelings, and decide if continuing the romance is the best move. There are some friends that believe you can never date anyone that they dated. If that is the case, you’ll have to choose between ruining a good friendship or throwing away a potential boo. Not an easy choice but the key here is communication with all involved parties.

When it’s not a date

You’ve gotten all dressed up and your heart is giddy with butterflies for this “date.” Towards the end of the night you mention how much fun you had on this date only to see his/her eyes wide with confusion. In their mind, this wasn’t a date but more so two friends getting together for a meal. Turns out the other person doesn’t have a romantic interest in you. Ouch!   How to handle it: Laugh it off. Don’t make it worse by asking why or pouting at the table. Sometimes we all misread signals and think something is more than what it is at the time. Enjoy the fact that you had a great evening and keep an open mind. Plenty of friendships turn into romance with time. For now, you can excuse yourself to the bathroom and make sure you wipe the egg off your face and take the foot out of your mouth.

You had a great date. Then you meet his girlfriend.

Saturday night you ran home to tell your friends about this great date with a wonderful person. Sunday morning you run into that same date at brunch, with their significant other. Now everybody has to die because you want to cause a scene and fling your unlimited mimosas right into his face. How to handle it: Recognize when something isn’t your battle. The universe was kind enough to let you not waste anymore time so take this chance run-in as a blessing. There’s no need to confront his girlfriend in the bathroom or go have a seat at their table and tell him how you had so much fun Saturday night. Keep it mature. Keep it classy. And let his karma come back to him in its own time. However, you are human so be petty. Delete his number and give a few side eyes to him over your eggs benedict. He deserves it.   Have you had any other awkward dating situations? Share in the comments below!   Dee Rene is the writer and creator of Laugh.Cry.Cuss., a faith based blog that finds valuable lessons in pop culture and every day life. She is based in NYC. You can follow her or the blog on twitter @deerene_lcc @laughcrycuss or visit the site at http://laughcrycuss.com.

Trending on MadameNoire

Comment Disclaimer: Comments that contain profane or derogatory language, video links or exceed 200 words will require approval by a moderator before appearing in the comment section. XOXO-MN