How to Break Out of a Dating Rut

This article is part of a series featuring Three Day Rule Date Coach Lindsay O’Shea. Check out more from Lindsay on our Date Coaching page.

“If do what you’ve done, you’ll get what you’ve always gotten.” –Tony Robbins

Break out of your dating rut! Ever feel like you meet the same types of people with different faces? Routines help us to organize our world, increase efficiency, and makes us feel more in control. BUT, routines also make it difficult to meet new potential dating partners.

Meeting new people can be scary. It’s normal to feel self-conscious around new people. Remember that name game icebreaker where you had to walk around memorizing colleagues names and a fun fact about them? Pretend a room full of strangers is the same situation. Practicing social skills on total strangers is great because you never have to see them again if you don’t want to.

1. Be genuinely curious about others

PeoplePeople can sense whether your questions are genuine or inauthentic. Everyone likes talking about themselves, so just ask questions! Find a common ground and go from there. Maybe you both have a passion for exotic birds. What is their favorite species? How did they get in to liking rare birds? Did they learn from their parents?

2. Check your ego at the door

egoNot everyone is going to like you, but if you’re a friendly person you’ll have a better shot. Yes, rejection is a possible outcome of talking to strangers but if that’s how they respond to kindness, that’s their problem not yours! Fear of rejection is a HUGE barrier that the majority of people in the world face, you are not alone! If you try to lean into the discomfort and put aside your own anxiety, you will reap the benefits. If your “true self” is really shy, put on a “false self” for the night. No, I’m not telling you to be fake, but try act like someone who is confident and outgoing. Force yourself to do this and break out of your shyness.

3. Be the middle person

middleUse your name and fact remembering skills to introduce people to others. By introducing someone using a name and fact, the person will feel closer to you because they will feel like you know them. Spend roughly ten seconds introducing yourself and another person.

4. Get out of your own way

judgeIf Kanye West can admit it, so can you! Recognize that people are so involved in themselves, they usually don’t have time to judge you. Everyone is self-conscious whether you can see it or not. Make sure you body language is welcoming and makes others feel comfortable.

4. Be present.

imageAdvancements in technology has conditioned us to multi-task like crazy. decreased attention span. People can tell if you aren’t making eye contact, preoccupied with something else. The best way to connect with someone is to, shocker, listen to them.

5. If at first you don’t succeed…


Too fast, too soon? Some say it takes 10,000 hours to become an expert at something. That’s a lot of socializing! Take baby steps, challenge yourself to talk to at least one new person per day. You’ll be working a room in no time!

Set up time to meet with Lindsay on our date coaching page, or email her at!


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