How to Stay Optimistic When Dating After Divorce

By Sandy Weiner, dating coach at Last First Date

It can be very challenging to date after your divorce. There are many potential obstacles to overcome, such as learning to trust, feeling good about yourself if you’ve been in a degrading relationship, and balancing work, kids, parents, and your own self-care. It’s a complex process, and it takes time to heal after divorce. This article is for those who have done the internal work and are dating again. Dating can feel disheartening at times, so I’ve provided some tips on how to stay optimistic throughout the dating process.

What’s your dating experience? Do you have first dates that don’t lead to second dates, and second dates that don’t lead to a relationship? Perhaps you have dates with no chemistry, or dates with off-the-charts attraction but no substance? Many of you have given up on dating altogether. You are not alone. In fact, you’re in great company. Welcome to Dating After Divorce 101!

The challenge is to keep on going, maintain your self-esteem after so-called ‘rejection’, and become a dating optimist.

4 Tips for Staying Optimistic When Dating After Divorce

1.  It’s usually not your fault. Most dates don’t lead to long-term relationships. You are looking for someone special, not just anyone. It takes time and effort to sift through potential matches until you find the person who’s right for you. You’re only looking for one great guy. Keep this in the back of your mind when a date doesn’t work out. The most important thing is to stay in the game, and don’t give up. It’s just a matter of time and effort before you meet your mate.

 2.  Sometimes it is something you said or did. First dates are all about first impressions. That’s why it’s important to watch what you say and do on your date. People misread cues all the time. After each date, it’s a good idea to review what went well and what you could do better next time. One of the big offenders? Absolute statements, such as ‘I never’ or ‘I always’. For example, what if you said, “I would never live in Manhattan,” but you meant, “I prefer the country now, but wouldn’t mind living in Manhattan when my kids are grown”? He may never call again, because he’s a city guy and you’re a country girl and he thinks it will never work out. This happens all the time. So, choose your words well and stay away from those absolutes. Stay open and curious, and things will flow much better next time.

 3.  Keep on going. It’s important to not come undone after each bad date. If you’re feeling down, get out and do something fun or nurturing for yourself. Get together with friends. Be good to yourself. And then get back in the saddle and go on the next date. And try something new. If one dating site is not working, try another. Try, a great way to meet people with common interests. He’s out there somewhere, but you will never find him if you’re hiding out at home, watching ‘Downton Abbey’.

4.   Be grateful. In order to move on in a healthy way, don’t dwell on what’s not working in your love life. Focus on what is working and be grateful. Develop a gratitude practice. Notice the wonderful things in your life every day. Appreciate the people who love you. You might want to make a gratitude list at the end of every day. Or find a ‘gratitude buddy’, a good friend you can call daily/weekly to chat about what you’re both grateful for. A good positive attitude is one of the most important things to bring on a date.

Become a dating optimist, and you will exude positive energy throughout your life. You’ll bring that good energy on every date. And when the right guy shows up, you’ll be irresistible to him!

Got any great tips for how you stay optimistic while dating? Please share below.

Note: If you want to learn the top three mistakes midlife daters make (and how to turn them around to find love now!), sign up here for my FREE report.

Bio: Sandy Weiner, Dating Coach and Founder of Last First Date, believes that the best relationships begin with honoring yourself first. Sandy is an internationally known dating coach, blogger and workshop leader, and a regular contributor to the Huffington Post on dating and divorce. Listen to her weekly radio show, ‘Courageous Conversations’, at Sandy is devoted to helping women over 40 break old love habits and achieve healthy, off-the-charts love in the second half of life.

9 Responses to “How to Stay Optimistic When Dating After Divorce”

  1. Paddy says:

    Don’t stress,and don’t act desperate. If you look desperate people can tell straight away and no one is looking for someone desperate. That automatically sends out a signal, be confident and appreciate the time you can spend getting to know new people and enjoy life and be happy. Not all dates will work out but the main thing is to be yourself… great article I love the optimism that you have laid out

    • Terry says:

      Hi Paddy, Sorry for the delay responding due to me travelling! I appreciate your insightful comments and I will pass them on to my guest blogger, Sandy Weiner. She is an amazing woman and author. Regards, Terry

  2. Sandy Weiner says:


    I just saw your comment on my guest post. Great tips. So many people give off an air of desperation or ‘pick me, pick me’! Confidence is so sexy to both sexes. And you are so right about focusing on being yourself, no matter if the date works out or not. More often than not, it won’t work out to become the relationship you were hoping for. Love is worth the wait. In the meantime, enjoy the journey!


    (Terry, thanks for your kind words. You’re pretty awesome yourself)

    • Terry says:

      Hi Sandy, You are welcome! I appreciate your positive mindset and I’m very grateful that you were able to read the comment. Your wonderful blog has helped hundreds of people and I look forward to you writing another one in the future! Regards, Terry

  3. tipsondating says:

    Thanks for making the effort to talk about dating. I experience highly about it and really like studying more on this subject. I have been browsing online more than three hours today, yet I never found any interesting article like yours. It is pretty worth enough for me.

  4. All of these are great tips – and I think there is another mindset to take – to really love yourself first – forgive yourself and fall in love with who you were created as, the purpose which you were designed for and the value you have already brought to people with whom you are in relationship. When you love yourself with all of your warts, others will be attracted to you just because they can sense the love and absence of judgment about yourself. What a safe space you create for them!

  5. TH says:

    I have been on the lookout for a good therapist that specializes in divorce counseling in west Los Angeles.

    • Terry says:



      I don’t have specific info about your area but recommend you contact the American Psychological Association (local chapter), your insurance company (if relevant), and look in your phone book under counseling. When you call for an appointment, ask if they have experience with divorce. If you have trouble – write me again!


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