Dating Doesn’t Have To Suck

Published September 27, 2016
Last updated June 4, 2026

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People love to hate dating. It makes sense if you’ve got the pressure of possibly screwing things up with a potential life partner with every swipe, text or email.  It’s hard to be yourself and know what you truly want with that kind of stress hanging over you.

Ways To Make Dating Survivable (and maybe even fun)

Keep Perspective: let it just be coffee, dinner or a walk around the lake. It is so easy to think about step 10 when you’re only on step one. Be deliberate about enjoying the moment with another human, even if you know you won’t be going on a second date.

Try Variety: the great thing about the internet is how it opens up our worlds to meeting people we would otherwise never cross paths with. Take the opportunity to spend some time with people you wouldn’t ordinarily pursue. The risk is low and it will help you refine what you like and don’t like.

Thicken Your Skin: rejection is part of the process. You are not going to feel it for everyone you go out with and, brace yourself… not everyone is going to feel it for you. That’s ok, it’s how it should be. There are 7.5 billion people in the world (2016), there is room to take your time and choose wisely.

Know When To Quit: not everyone communicates clearly. If you are operating in the absence of information from the other person it is probably time to take a step back. Don’t expend energy towards someone if it isn’t reciprocated.

Know When To Lean In: intimacy and connection can be scary at times, especially when a relationship is new and untested. Finding a balance between taking a risk and keeping yourself emotionally safe can be a fine line that doesn’t always feel good.

Practice Vulnerability: if there is one thing I’ve come to realize it’s that people are craving connection; they just don’t do it very well. If you’re tired of having the same date over and over again, shake things up by setting a rule of no small talk the next time you meet someone new. Need some help? Check out this article from the New York Times.

How Long Should I Wait To Date After A Breakup?

It depends on a number of things including the length of the previous relationship, the nature of the breakup and the goal of getting back into dating. There is really no magic length of time. Sometimes it may be appropriate to rediscover what makes you happy outside of being in a relationship. Other times it may be helpful to lean in and connect with someone new even when you don’t feel quite ready.

Regardless, take time to process, mourn and integrate lessons; the end of a relationship has a lot to teach. If you have a pattern of jumping from relationship to relationship you are probably cheating yourself out of the opportunity for real growth and insight. Grief and loss are tough issues to confront but doing the work in the present can save you from heartache in the future.

What Do I Do Now?

Sometimes when you’re in the middle of something it’s hard to see your way out. Friends and family members may be important for support but they may not be the most objective source of feedback. Working with a counselor to identify fears and maladaptive patterns of behavior can help increase your chances of enjoying and maybe even finding success in dating.

If you want to have more success in the dating world, let’s talk!



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About
Michael Hilgers, M.MFT, LPC

I’m a Licensed Professional Counselor working remotely with clients around the world. I believe that everyone has the potential to change; to create new paths, to go in new directions. Life is hard. Counseling can help.

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Michael Hilgers, M.MFT, LPC

Michael Hilgers, M.MFT, LPC

Licensed Professional Counselor | M.MFT, LPC

Michael Hilgers is a Licensed Professional Counselor (LPC) and Licensed Professional Clinical Counselor in New Mexico, with a Master’s degree in Marriage and Family Therapy. In clinical practice since 1996, with an estimated 20,000+ direct client hours, he specializes in online therapy for adults — including entrepreneurs, attorneys and creative professionals — navigating anxiety, depression and relationship challenges.

His work focuses on attachment and relationships. He has been quoted in The Atlantic, HuffPost and New York Magazine and has been a guest on the Therapist Uncensored podcast. More about Michael

Licensed in Texas (#17131), New Mexico (#CCMH0213561) and Florida (#85).

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