While dating someone new, conversation can be going smoothly one minute, and the next, you’re texting your best friend the signal to help you fake an emergency that will allow you to disappear in a cloud of smoke on a suddenly awkward date. Just because an almost-stranger suddenly brings up politics or religion doesn’t mean you have to stop imagining what your first name might look like in front of their last name! You were into him a minute ago, and you’re definitely not the first person to encounter an awkward speed bump in conversation during the first stages of dating, so power through it, and opt for the fight option in your fight or flight reaction. At the very worst, it will make for a good story with your friends later and will build you some character. At the very best, a story at your wedding!
Below are five awkward date moments and how to overcome them:
1. The Awkward Silence: Sometimes we are so busy stressing out over what our date thinks of our restaurant/outfit/drink choices that we draw a blank when it comes to conversation. It can be difficult to integrate questions without sounding like you’re conducting a job interview. Usually, if your date is a good fit, you’ll naturally fall into conversations about interests and hopes and dreams and all of those nice things, but it doesn’t hurt to have a few topics in the bank that you can reference during a lull. Ask them what superhero they would be, or recall a funny anecdote from your week, or if all else fails, you seriously can’t go wrong with talking about food.
2. The Money Talk: Surprisingly, I’m often reminded by single colleagues and friends that people are missing the memo that preaches the importance of NOT asking someone how much money they make early on in a relationship. Maybe their mother never told them that it’s majorly weird and rude, or maybe they are just super open like that and assumed you were too, or maybe they got caught off guard by your unique career … Regardless, it doesn’t automatically make them a bad person or a class-five gold digger, but you should let them know it’s a little too soon for that sort of talk. Try saying, “I have managed okay so far, so I don’t think you need to worry about it” or “We haven’t even moved in together yet!”
3. The Ex Factor: If your date asks what your last relationship was like, or why it ended, it’s completely up to you to decide the level of detail to disclose on whatever timeline works for you — although the first few dates may seem a little soon for that. Light-heatedly remind your new friend Curious George that it just didn’t work out, and you are glad for it, because now you’re there with them! Just keep the conversation moving. On the flip side, if your date is repeatedly bringing up their exes, quietly file that under the label: “Red Flags”.
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