11 Ways To Stay Positive When Dating Feels Like The Worst, According To Matchmakers

by Kristine Fellizar
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With every first date that leads to nowhere or every non-relationship that ends up being a waste of your time, finding love can seem far from possible. It can also be pretty rough on your self-esteem if you continually put a lot of effort into dating without getting much back in return. But you shouldn't let dating drag you down. According to matchmakers, there are ways you can stay positive when single, and dating is making you all sorts of frustrated.

"The pressures of dating stem from the need to uphold a dating mask," Julia Armet, Director of Operations at matchmaking service, Tawkify, tells Bustle. "We all fall into the game of dress-up, with social masks being one of the greatest blocks to establishing true intimacy."

It's true. How many times have you been advised to be yourself, but only the best version of yourself, when you're on a date? The same applies to dating profiles. While it would be great for everyone to be their authentic selves online, that's not typically the case. People usually showcase the highlights of themselves online because it's important to stand out in the best way possible. Pretending to be this perfect version of yourself can be exhausting, especially if none of your dates actually end up turning into something more.

That's why, if you really want to stay empowered when you're looking for love, Armet says, stop dating and start connecting. "Human-to-human vulnerability is the natural consequence of two people allowing their inner selves to shine," she says.

So here are the best ways to stay empowered when dating is bringing you down, according to matchmakers:


Start Saying "Yes" To The Things That Scare You

If dating has become an endless cycle of the same thing every time, start saying yes to things that will push you out of your comfort zone. For instance, if your co-workers invite you out on a weeknight, say yes. Better yet, change the distance settings on your dating app. If someone asks you to come visit them in their city, don't be afraid to go for it if you're really connecting with the person.

"This will change your relationship with others and yourself," Michal Naisteter, Philadelphia-based matchmaker at Three Day Rule tells Bustle. "Think Year of Yes by Shonda Rimes. A practice like this will bleed into all areas of your life and will open yourself up to new experiences as well as your own empowerment."


Be Grateful For The Life You Already Have

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You probably hear this a lot, but start a gratitude journal. Whether you like it or not, Naisteter says a gratitude journal will reshape your thinking fairly quickly. You can spend time once a day or once a week reflecting on what's good in your life or what went well that day. "Some people do it at night by writing in a journal, putting notes in a jar or just thinking the ideas out loud," she says. "These positive ripples will slowly affect your week and your dating life."

It doesn't have to be a difficult or long process. As Professional Matchmaker with Tawkify, Alyssa Bunn, tells Bustle, just spend one minute looking for three to five positive things that happened each day. "Gratitude not only helps us feel more confident, but it's scientifically-proven to help us win new relationships," she says.

When you're more grateful for the life you already have, you're more likely to see dating as a fun way to meet new people and not a challenging task that isn't going anywhere for you.


Don't Approach Dating Like A Part-Time Job

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"A lot of people approach dating like a part time job," Michela Hattabaugh, Chicago-based matchmaker with Three Day Rule, tells Bustle. Meaning, they'll shoot for a certain amount of dates per week and spend a good amount of time on various dating apps a day. When dating becomes something you have to do each week, it's going to burn you out. It can also kill your confidence when you're not hitting certain goals you've set for yourself each week.

While it’s true you need to make time for dating, make sure you’re also building in some "me" time, Hattabaugh says. Take a yoga class or do something relaxing to help clear your mind and boost your sense of well-being. "Adding in a few hours a week to focus on relaxation will improve your overall mood," she says.



Remember That Dating Is About You Too

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Many people tend to feel like dating is about whether or not they appeal to the other person. But as Hattabaugh says, "It takes two to tango. You should approach dates with confidence." Instead of thinking, "I hope they like me or I hope I don't act too nervous or weird," think, "Does this person have the kind personality that I deserve in a partner?" Self-defeating thoughts will only bring you down and affect your overall demeanor. "Always remember that you’re a catch and approach the date with that mindset," she says. It's all about loving yourself first.


Chart A Path To Forgiveness

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If you have trouble believing that you are enough and the right person really is out there for you, you may need to dig into your past to heal some wounds you probably didn't know you still had. "Think about what has hurt your heart in the past and be intentional about forgiveness," Bunn says. "Forgiveness creates hope that the past could be different. Until you fully heal, your past dating wounds will fester, clouding your judgment and obstructing your growth."


Recognize That You Hold The Power

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"You don't need to be empowered, you already have the power," Professional Matchmaker with Tawkify, Melissa Roy, tells Bustle. Don't fall into that trap of thinking another person has the upper hand on your happiness. "You get to choose who you spend time with and who you want to be intimate with," she says. "That's what dating is all about and it's awesome."


Don't Be Afraid To Tell It Like It Is

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"If you really want to be empowered, speak up," Professional Emissary at Tawkify, Evyenia Trembois, tells Bustle. This comes in the form of choosing the date location yourself, picking out a place you've been curious to try, or ending the date early after coming to the conclusion that it's not a match.

Furthermore, own your time. As Professional Matchmaker at Tawkify, Sophy Singer tells Bustle, "Shut down those endless texting sagas that lead nowhere. Create rules and stick to them." Don't entertain people who'll flake on you or can't commit to meeting up for a 15 minute coffee date.

Above all, recognize that you don't ever have to stay in a situation that isn't serving you. "Women are conditioned to be 'polite' in dating situations, even at the cost of our own fun, enjoyment, and time," Trembois says. "But the bottom line is, you really don't owe anyone anything. Have your own back, and do what feels right for you. Thats's empowering AF."


Listen To Your "I'm All That" Anthem

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Turn on that song that makes you feel like you can take on the world. If you don't have your own personal anthem, "Listen to Beyonce's 'I'm Feelin' Myself,'" Rémy Boyd, Professional Matchmaker with Tawkify, tells Bustle. Apparently, it's the ultimate "I'm all that" anthem that can help shift your mindset to "I'm in the driver's seat." When you have that revitalized confidence, take some new pics, redo your dating profiles and start fresh. "Be the person you'd want to date and you'll start catching the best fish in the sea," Boyd says. "This is the one aspect of dating you can control, so own it!"


Take It Slow

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When you're in a rush to just be in a relationship, it can cause you to settle for someone who might not be the best possible match for you. But relationships are tough and you have the rest of your life to get serious. So spend your time being single to explore your options. "Give yourself the opportunity to meet new people as often as possible and create meaningful friendships," Boyd says. "The best relationships begin with a solid foundation of friendship. Why? Because there's no pressure in the beginning! Slow down and let love happen to you." There's nothing more empowering than realizing your patience really paid off. You didn't let external factors influence your decision to get into a relationship. You took it slow and made the right decision for you.


Refuse To Give Up

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Dating isn't about striving for perfection. "It's about showing up and giving it your all," Bunn says. "When you bring that effort to every date, true love has the ability to fall into place." If you want to stay confident even if your dating life is less than ideal, recognize that you really are worthy of love. A good partner is on their way.


Don't Be Attached To Any Specific Outcome

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Do things that make you feel happy. "Create goals you want to work towards," Caitlin D'Aprano, Professional Matchmaker at Tawkify, tells Bustle. "Self-esteem is built by the things we achieve, not the number of romantic partners we've secured!"

So focus on the positive things that you can bring to a relationship and the positives of being single. Make an effort to meet one new person a week, whether it be a friend, a hook-up, or just anybody. "Don't be attached to a specific outcome and just be in-the-moment with people you meet," she says. "You will find that you're attracting quality people who are naturally drawn to you."

When it comes to dating today, you can pretty much expect disappointments to happen. But stay positive and keep going. As long as you stay confident and true to yourself, you will attract the right partner for you.