Amanda Cunningham: Dating At 38

“Rip the bandaid …”

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Never something I thought I’d say, or do. When I started dating I was still knee-deep in my separation. But I had been alone for so, so long – I was desperate for connection. I needed to be wanted. It was my therapist that pushed me to start. It had been 12 years since I dated last, and 3 years into what would turn out to be a 5-year-long road to divorce.

She said, “I know you heard me. I know you understood. I saw you do the work. But I don’t know if you will integrate it, until you integrate it. So get out there”. She wanted me to practice all that I had processed.

I was fucking terrified. So this if for those who are, too. Rip the bandaid, have fun rediscovering yourself, and take (with a grain of salt) from what I learned …

1. You’ll be nervous, but it’s like riding a bike. Soon you’ll appreciate the freshness of new faces and conversations.

2. It’s okay to go on dates before you feel ready. Pretend it’s a networking opportunity and treat it as such – you’ve already learned to drop expectations, why stop now? (kidding!) Every date, and every person, is an opportunity to learn something.

3. You can cancel a date because you feel too anxious, too tired, or too anything. Your time and who you spend it with is sacred.

4. Give yourself freedom to be free. Own that wild stage! Go on too many dates, have too many drinks, dance till 2am and make (a few) bad decisions.

5. The first time with someone else might feel wrong. Or exhilarating. You may have guilt or you may feel free. Be in that moment, and let all the feelings surface.

6. Plan short dates – coffee, a walk, just one drink. If you hit it off, you can always stay longer. But if you don’t, you have a way out.

7. You’ll go through phases. You’ll be on all the apps and say yes to all the dates – and then you’ll be exhausted or disheartened with it. Taking breaks to recalibrate with yourself is healthy.

8. The qualities I looked for in a partner 15 years ago are drastically different from what I look for today. Write out your non-negotiables – and don’t compromise on them.

9. You don’t have baggage, you have stories.



10. Even if you go on a 100, first dates always carry nervous energy.

11. Some deserve a second date.

12. Chemistry is not compatibility.

13. Sex is not connection.

14. Emotional depth is not emotional availability.

15. It’s okay to casually date someone you have fun with. It’s okay to know he’s not the one, or long term. Have fun, you deserve it. Everyone serves a purpose (and sometimes you serve the purpose in someone else’s journey).

16. Ghosting is real. It is not you. Repeat that often. It is not you. It is them. Hold yourself and others to higher standards.

17. Don’t chase love. If they like you, you’ll know they do.

18. Stay in therapy. Talk about your experiences. You’ll uncover who you are, what you want, how your past affects you. How your childhood does, too.

19. You may find you enjoy being alone. You may actually prefer it.

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20. Apps give a false sense of rejection. A swipe left means absolutely nothing. Be mindful of this for your mental health.

21. Apps offer quantity – go for quality. Or ditch the apps and do it old school.

22. You’re not 22 anymore – so be who you are today – without hesitation. But see yourself as that innocent 22-year old again, every move you make should protect that version of you. If it’d hurt the young you, don’t do it to the adult you.

23. Take them for face value.

24. Be honest if you aren’t feeling them. With yourself, and with them.

25. It is okay to ask about politics, religion and familial relationships. It’s okay to talk about your kid, your ex and your red-dye allergy. If it offends them, they aren’t for you. There’s balance in everything.

26. Learn to ask better questions. Are you an entrepreneur, or does your dad still give you an allowance? Did you graduate from Ole Miss, or do you just own the shirt? Are you conservative, or are you crazy enough to vote for Trump in 2024? Do you read? Books?

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27. It’s okay to have a minimum salary requirement. More often than not this equates to intelect, drive and ambition. It should never be the box, but it can be a box. It’s about aligning lifestyles, goals and trajectories.

28. Give yourself a drink maximum. You make better decisions when sober.

29. Reflect. On what you said, asked, the way you acted, what you wore. Did you represent yourself fully? Did they?

30. Most of us are confused about gender roles. Explore this. Who cooks? Who cleans? Who pays the bill? Who does what, and why?

31. Wait to sleep together. I was told there’s a three date rule. But also, fuck rules.

32. Keep some things to yourself. Our new partners don’t need to know every detail of our past. Some memories are just for you.

33. Someone might check nearly all your boxes, but you just aren’t in love with them, that’s reason enough to walk away.

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34. Your heart can love again. It can break again, too.

35. Date men your age, or older.

36. Offer to pay if you want to pay, but when they let you, don’t judge them. See #30.

37. Having a job and texting back is less than the bare minimum. Do not uncheck your boxes because you feel like you won’t meet someone better. Hold them to a standard you didn’t the first time around. Do not settle.

38. You can change your mind at any time. You can be into men, and then women. You can want to be married, or single forever. You can want another baby, and then not. This is the part of being single you should revel in.

39. Notice yellow flags = things that need to be explored further. Don’t ignore the red ones. Sometimes your anxious attachment style is actually your intuition telling you something is off, trust yourself.

40. You have to love yourself before anyone else can. You are enough. You always have been.

40 rather than 38, cause I hope I don’t learn another fucking lesson for a few years. Gawd knows we all need a break.



Amanda Cunningham (Provided)

Amanda B. Cunningham is a guest contributor for FITSNews. Additionally, her work has been featured in Redbook, Healthline, Bustle, Natalist, The Native, SWAAY, DIY Active, Yoga International and Udemy. Amanda runs operations and development for an anti-trafficking nonprofit and is a Sisters On The Planet Ambassador for OxFam America. She lives in the Lowcountry with her 5-year-old son, often found swimming, eating pizza and building legos. This column - reprinted with permission - first appeared on her website.


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Avatar photo
The Colonel Top fan July 28, 2023 at 9:47 am

Love it – relationship advice from a divorced, single mother who married a narcissistic man child… At least she appears to have learned a few lessons from her time with the “ocean engineer”.

Troublebaby July 28, 2023 at 10:01 am

She’s most likely a narcissist too…..

Flossip Top fan July 30, 2023 at 9:21 am

Judging by the psycho-babble above, yep. And then some.

Avatar photo
Joy Gmmon Top fan July 28, 2023 at 9:53 am

Smart woman.

Michael Top fan July 28, 2023 at 9:54 am

Very interesting, Amanda. As a guy way past the age of dealing with dating, and long married anyway, a couple of reactions: be honest with the guys. Pay for some of the dates. If you’re so proud of your career and independence, pay your way sometmes.

tbrewer1 Top fan July 28, 2023 at 11:02 am

Why do you have to use the F word ?Its not a very classy way to express yourself?

Goody3 Top fan July 28, 2023 at 12:02 pm

Just NO.

Amanda Williams Top fan July 28, 2023 at 1:24 pm

Time has not changed her snark. She’s still an entitled crybaby. Go away.

Jackie July 28, 2023 at 4:28 pm

Even more ridiculous than I anticipated.

Bye Felicia July 28, 2023 at 10:32 pm

Nobody cares if you’re dating, let alone doing the horizontal monster mash. Just fade into obscurity already, geeze.

Happy&Lucky Top fan July 30, 2023 at 6:23 am

Please find a new therapist.

Flossip Top fan July 30, 2023 at 9:23 am

The interesting thing here is that she would never have been given space on this website if not for who her former husband formerly was.

Thomas July 31, 2023 at 7:58 am

cut the chase down

41) When was the last time you were in a hotel, why?
42) When you look in a mirror, what do you see?
43) Who was President when you were born?

41) To visit my sick relative is the desired answer
42) You see a mirror, any other answer…avoid them
43) If they do not know, pay the check and leave

Frederick Barton Top fan July 31, 2023 at 8:00 am

Bless her heart!

Amanda knows the key is to always fellate on the first date. She likely learned that in the 7th grade. Gotta get nasty.

choo choo July 31, 2023 at 11:59 am

Train wreck……

E Prioleau Alexander Top fan July 31, 2023 at 2:21 pm


If you’re reading these comments, remember most are written by male losers who hide behind fake names. None have never dated an attractive woman. Several live in Mommy’s basement, where she brings them tomato soup and a grilled cheese sandwich everyday.

And, they’re most liberals. You should try going out with an educated conservative guy. You might find someone who doesn’t wet the bed every time Trump is brought up.

Best of luck going forward!

Anonymous August 1, 2023 at 10:47 am

If you mention “intellect,” at least spell it correctly (see #27)…


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