83 Awkward Conversations That Showcase Online Dating In A Nutshell, As Shared On “Overheard Dating”

Online dating is a lot of fun, from the sidelines. Just two people trying to get to know each other from nothing but a profile picture and a short bio. It’s an awkward conversation factory that keeps on giving. 

The Overheard Dating Instagram account gathers all the funny, awkward, and strange conversations people have encountered when texting a possible partner. We also reached out to James Preece, a dating coach & relationship expert to ask some questions about finding love in the 21st century. So keep scrolling, upvote your favorites, and check out Bored Panda’s other article on online dating conversations here. 

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We wanted to know how best not to lose heart in the turbulent waters of online dating. “It's so important not to get disheartened. Every person you meet or interact with means you are one step closer to getting the relationship you dream of. If you stop now, you'll never know if the very next person (or the one after that!) might just be the one. Rejection is never personal as we are all looking for different things. Instead, view every date or conversation as an opportunity to have fun and learn from someone new,” James advised.

We also wanted to know about setting healthy boundaries at the start of pursuing a relationship. James suggests that “if you accelerate things too quickly then you'll eventually hit the problem where you run out of steam. There's no reason to commit to one person until you are ready. You have to keep exploring your options to make sure and work out what you really want. After all, you wouldn't stop going for job interviews until you've got a job. Therefore, it's important to set some realistic expectations right from the start so you can be sure you are attracted to them on all levels - rather than just physical desire.”

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“Things are becoming serious once you find that you are spending more and more time with someone and starting to miss them when you aren't together. You'll probably begin to be a little more emotionally invested in them and you may even experience a little jealousy as you become attached. It's also a big sign when you are making plans for several months again - such as a holiday or meeting friends and family,” he added when clarifying how best to understand when your relationship has exited the initial stage and is becoming more serious. 

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James had some final advice for people who have just started dating for the first time or after a longer hiatus: “trust your gut when it comes to dating. If something doesn't feel right or you feel you are making excuses for someone, then they probably aren't your person. It's important that you take the time to get to know someone, so you'll know if they are treating you with respect and as a priority.” You can find his site here or his podcast here. 

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Online dating has a pretty negative reputation, if not for its awkwardness, then from the constant churn of texts and rejection. The Pew Research Center has found that roughly one in three Americans have used an online dating site or app, but only a measly 12% actually went on a date or married someone they met over the internet. Despite these pretty low numbers, most users are still satisfied with their experience, since it’s probably nicer to get left on read than to be rejected to one’s face. 

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The same research found that women are more methodical when analyzing a potential date's profile, and most (72%) indicated that they had specific criteria they looked for. Men, the raccoons of the internet seemed content to take whatever they could find. This could also be because most men reported getting fewer messages and responses than they would have liked. Beggars can’t be choosers, it seems. 

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Roughly a third of women reported having to often deal with overly persistent suitors (37%), unsolicited images (35%), and even harassment (28%). One in ten even experienced threats online. All of these numbers are even higher for women between 18 and 34 years of age. Given the dangers, most men should be happy enough that any women are willing to brave a dating app or site. 

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