5 Deep Questions To Ask Yourself If Dating Feels More Stressful Than Fun

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Am I Ready For A Relationship? How To Start Dating Advice
Love, Self

When you first start dating, you're full of happiness and excitement. Over time, however, that pursuit of happiness may dry up and leave you wondering if it's time to stop going on dates and instead figure out how to change your life for the better.

If going on a date doesn't appeal to you anymore, it's time to ask yourself how to be happy again in a new relationship. Dating should be exhilarating and fun; but chances are good that after a while, you're going to start feeling like you're never going to find a good person to settle down with.

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Though I am no longer a part of the dating game as I was when I was younger as a free-spirited artist type in New York City and Europe, I see a lot of the dating issues come up for women I meet.

These women are often going through a life change, which may be a breakup or the stress of trying to find the right life partner.

Here are 5 simple questions you need to ask yourself about dating that will help you understand how to be happy doing it again:

1. "How am I meeting guys?"

Many women are doing the online dating or app dating and going from one “possibility” onto the next, like shopping for a new pair of shoes — oftentimes off of a picture alone

This happens because the guy does not meet your “criteria” and you're not satisfied with things you see about him right away.

If the way you're meeting men isn't working for you, try something new. If you normally date online, try going out and talking to people in your favorite coffee shop, or bookstore, etc.

Likewise, if you don't really get the opportunity to meet people in your regular day, try out a new dating site or app for a few days. Switch things up to reintroduce fun!

2. "Am I really giving this guy a fair chance?"

Are you juggling more than one guy at a time? This may not be the best use of your energies. I have been there before, dating three guys at a time, and it is a juggle that can be very draining.

It’s like multi-tasking dating. If you are like me, multitasking is a drag and makes you inefficient at best, tired at least.

If dating more than one person — or even just talking to several people at once — is dragging all the fun and happiness out of your dates, try to simplify things.

Talk to or see just one person at a time. Give them a real chance to impress you and to learn new things about them that interest you or that you may have in common.

3. "Am I moving on too quickly after my last relationship?"

A lot of women move on quickly, sometimes because a guy rejects them, or sometimes because they don't want to be "alone." Rejection and fear hurt every time, even if you don't admit it.

No one is perfect. If you're more interested in just moving onto the next person rather than taking the time to know and trust someone, you're missing out on a crucial part of dating.

Taking time to heal after a breakup, even if you're the one who cut it off, is important. You don't want to bring those disappointed rejected feelings into the next “try" and cripple your new relationship before it has a chance to really even begin.

Make sure you're in a good place mentally to start dating again before you go out so you can get the most happiness and fun out of it as possible!

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4. "Am I dating to fit my needs only?"

While it is important to know why you're out there dating, a good question to ask yourself is: "What do I offer in a relationship?"

If you're looking to fulfill your needs only with a new partner, you might want to find a good therapist to help you with your self-esteem. The guy you are with is not going to fill that gap.

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Your goal should be to become a happy and complete person on your own so that you can attract a happy and complete person into your life.

This way, you are both going to make each other's lives better while dating, not worse. Dating should be done because you want a partner — not someone who will just fulfill a need for you.

5. "Am I trying to fit dating into my life like just another activity?"

Some women who struggle to find happiness in dating are often already married — to their jobs, that is! As a result, dating ends up being a small portion of your schedule you fit in like going to the gym, or getting a coffee with friends.

How willing are you to make the time for dating and is it eating into time you need for yourself? Relationships take time and effort, so they can't just be crammed in where you have spare time in your schedule.

Are you ready to do the work and make time to find happiness in dating again?


Make sure you're working on yourself daily. Breathe, exercise, hang out with friends or pets or family that make you feel loved, and don't have an agenda for being with the other person.

Just enjoy yourself, get enough rest, and eat well so you're not just dating whenever you have free time; you're doing it because it makes you happy and brings you one step closer to finding your life partner.

Get yourself a massage, be involved in life and activities you love, like yoga or rock climbing. The right guy might just be there in the shadows, ready to pop into your life when you least expect it, as your life evolves.

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Donna Davidge has been teaching yoga/meditation for over thirty years in NYC and owns and operates Sewall House Yoga Retreat in Maine, May to Oct since 1997.