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4 Ways to Not Be Awkward at Online Dating

Have you considered online dating? Last week I gave three reasons why you should. So now that you’re convinced to give it a try, let’s discuss how to actually be good at it. Online dating is a little like interviewing for a job — you want to stand out in a crowded field and be someone that a boss (potential suitor) would actually want to hire (or initiate communication with). After six months navigating this process last summer, I have a few thoughts on how to not be awkward at online dating or how to ace the interview and get the job!

1. No bathroom mirror selfies. The reality is that pictures matter in online dating. So do yourself a favor and find someone to take some decent headshots of you. Your standing in front of a mirror with your face obscured by your iPhone flash does not count. And if you don’t have a friend or family member who you can ask, then download a free self-timer app for your smartphone and say cheese! When the potential girl or guy of your dreams is looking through pages and pages of matches, the profiles with good pictures that highlight your best features are the ones that stand out. Be the guy or girl who stands out.

2. Decide how you’ll handle getting matched with someone you know. If you live in a small town or keep your matches within a short distance, the chance of this happening is even greater. The first time I tried online dating, I was matched with a good guy friend of mine. At first it was awkward because neither of us knew the other was doing it, but it actually forced a much-needed conversation about our friendship, which at times entered friendlationship territory.

Are you going to laugh about the situation? Will it make your next small group meeting awkward? Think through this scenario and come up with a plan for if or when it happens.

3. Momentum matters. It’s important to keep things moving forward, no matter how you meet. If the dating site you’re using has steps to communication, be prompt and don’t wait weeks to respond to a message. If you can communicate with matches directly, ask interesting questions and keep a good pace. If you find someone you’re interested in, make it a priority to meet in real life sooner rather than later. There are many stops in the journey from an initial match to going on a date, like becoming Facebook friends, texting, emailing, talking on the phone, Skyping, etc. The how is less important than the when, so make a plan to keep things moving forward.

4. Communicate a thumbs up or a thumbs down. The benefit of online dating is quantity, but not necessarily quality, meaning you might go on a lot of dates with people who aren’t a good match. That’s OK; it’s part of the process. But it’s helpful to communicate when you aren’t going to continue a relationship. Whether you’ve been emailing someone for a few weeks or whether you’ve gone out to dinner, if you decide it’s not the right fit, let them know. Just a simple “hey, I enjoyed getting to know you, but I’ve decided to invest in another match instead” is all you need. It’s helpful for both parties to know if they should keep a match open or closed, so be respectful and communicate when you’re closing the door.

What else would you add to the list? If you’ve done online dating, what stood out to you that your matches did well? Next week I’ll offer tips on how to keep God part of the online dating process.

Want to give online dating a try? Check out and use the promo code BOUNDLESS to get some extra days to your free trial.


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