5 Tips to Help You Keep Dating, Even When it Sucks

Mother and daughter talking about dating

Yesterday I wanted to quit. This is too hard. There are days things seem to be clicking and I’m finally getting it… marching boldly toward my goal. Then there are days like yesterday when I feel clueless… like a failure with no hope of success.

And I can’t help but take it personally. I know I shouldn’t. But this is one of my biggest challenges.

I see women all around me succeed brilliantly. I know deep down I can do it; I’ve been working at it and learning. But I feel like I’m missing something other women understand. Or maybe they have personal traits that I just don’t have.

I’m scared. Maybe I’ll never achieve my hugest, most burning wish in my life: to change the lives of tens of thousands of women by helping them find meaningful, wonderful, completely fulfilling and lasting love…as I have. (Which was my previous hugest wish that I checked off my list 5 years ago.)


When things get really bad like yesterday, I start thinking that my old life wasn’t so bad. Yes, there were many days I hated it and hated myself for not making the changes I know I needed to make. Yes, I constantly felt an emptiness; like there was something better in life for me.

But I tell myself: it wasn’t  t-h-a-t  bad. Maybe it’s time to give up and just settle with that life.


Then, I get an email from a woman who needs my help. Or a call from someone I’m coaching telling me she’s feeling hopeful and due to her newfound confidence and lightness, she is happily dating some nice men.

I talk to my coach, and she lifts me up and keeps me on track. (Yes! I have a coach too. She’s my biggest cheerleader and gives me invaluable direction and support.)

I start remembering how unhappy I was in my old life; that I promised myself I wouldn’t go back no matter how hard it got. What I’m doing is too important to me. It fills my heart and makes me feel like I matter. It adds something spectacular to my already great life. I’m proud of what I’ve done so far. I’m helping people.

So, I decide that I’m going to stick to it, even when it sucks.

And on I go to shift what I need to shift, and learn what I need to learn. I can do this. It’s worth it.


This is my story, but I’m guessing that if we replaced my goal with your goal of wanting the love of a good man in your life…it can be your story.

If, like me, you feel like giving up, or you’re lurking and haven’t even started…here are my 5 tips to help you stick to dating, even when it sucks.

  1. 1. Keep your eyes on the prize.

Whether your goal is to find everlasting love, or to simply enjoy dating and find a companion, keep focused and try to shut out all the other noise.

Be honest with yourself about what your life is like without it. Remind yourself that when you find him, your life will be filled with love, affection, security, good times and [you fill in the blank]. And that you can have fun along the way.

Here’s an extra little goody that is one of my favorite parts: you will have an enormous amount of self-pride for sticking to it and getting it.

  1. 2. Have fortitude and courage.

Not only do you want this and deserve it, you have the wherewithal to get it. Stick with it, accepting it can be hard at times.

We all experience rejection, confusion, self-doubt, and fears of all kinds when we actively pursue our dreams. Remember that you have a ton of life experience, attitudes and skills that have helped you deal courageously with all kinds of challenges in your life. (This is especially true for we women over 40…okay…well over 40.) Reach for those when you need to. They are just below the surface and often – for some reason – we just don’t apply them to dating and our search for love.

  1. 3. Change it up.

If you’re reading this, what you’re currently doing probably isn’t working. As long as you stay the same and keep doing things the same way in your search for a grownup relationship with a good guy, you will remain in the same situation.

Some of us consider change as an admission that we have been wrong. I know that was part of my problem during my almost 30 unsuccessful years dating. So we resist it; who wants to be wrong?

Welp, the good and bad news is that this is all about you. You need to become the woman who attracts that guy who can’t resist you and can’t do enough to make you happy.

Embracing change, learning and growing is the only way you can make this happen. Forget wasting time with blame or self recrimination. Be excited about what’s coming next, and congratulate yourself for where you are today: ready to move forward and go after the happiness you want in your life.

If you’re resistant, start with some easy and fun changes. Start wearing lipstick every day. Buy a new bra. Click here to read my post “Do Something Different Today to Improve Your Search for Love for these and other simple ideas to help you ease in.

  1. 4. Perspective, perspective, perspective. Being rejected by a man or feeling like you’ve ruined an opportunity for connection with a (potentially) great guy can feel incredibly crappy. But I’m guessing that if you gave it serious thought you’d realize that it’s a minor obstacle compared to what you’ve risen above in your life.

When I do one-on-one personalized coaching with women, my first step is helping her Fall in Love With Herself. A part of that is listing all the things she’s achieved and overcome in her life.

Do this exercise. Take your list and compare it to the experience of a man you don’t even know saying “no” to you. You’ll realize that it’s really no dang big deal. Then you’ll say “next” and keep going. (Return to tip #2.)

  1. 5. Get to work…today.

A note I have in my office says “Have the courage to put one foot in front of the other and do something.” Sometimes it’s that “do something” part that’s the hardest.

If you’re stuck – whether you’re not dating at all or you’re repeating bad experiences – promise yourself that today you will take the first step toward getting that date, that man, that marriage…whatever your dream.

Buy a book*, ask a woman in a good relationship for her advice, make a list of all the nice men you’ve known in your life, call the guy who got away, sign up for a fun or interesting Meetup group, hire a dating coach, or plan a night out with a single friend. (But only friends who love and appreciate men!).


As for me, ladies, I’m off to get ready for my Free for All call tonight where I will have another opportunity to be reminded of why I stick to what I’m doing: because I love it and it helps women find love.

* Here are just a few of my book recommendations:

Meeting Your Half Orange by Amy Spencer (For an upbeat and positive look at dating. My story is in here!)

The Unofficial Guide to Dating Again by Tina Tessina

If I’m So Wonderful Why Am I Still Single? By Susan Page

Making Sense of Men by Alison Armstrong

The Tao of Dating: The Smart Women’s Guide to Being Absolutely Irresistible by Ali Binazir

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