Dating Advice: Start with a List

Starting to date after a marriage has ended can be difficult. I often hear, “I never thought I would be doing this again.” After spending most of my adult life with the same man, I was not prepared for dating at 39 either. Regardless of whether meeting someone new involves sitting on a barstool, through a social club, speed dating, or the internet, it should all start with the same thing: knowing what someone wants in a partner.

The following advice was learned the hard way; I started dating before having a clearly-defined idea of what I wanted in a partner and, as a result, ended up in a relationship with a man who was wrong for me. My first dating experience post-separation would not have happened (or would have ended quickly) if I followed the advice I give now.

The best advice I could give to someone starting to date:

I also broke each of these rules in the last year. I would get involved and forget to revisit my list. I would fail to edit the list after a break up. I also tucked away incompatibility issues, ignoring the obvious, because a guy was fun on a date or because someone was nice and I should try to like him more. Each time I went against my own advice, it was a mistake.

Conversely, whenever I followed this simple advice, it was a success. I had a lot of first-and-only dates, quickly assessing a man and knowing there was no chance we would be a good fit. I was also able to end relationships fairly quickly after learning more about him, realizing it could not progress further.

A year later, my list looks different than it did after publishing my first version, but still has many items from a year ago.

Here’s my current list:

  1. Happy and fulfilled in his own life.
  2. Loyal and honest.
  3. Laughs often, with a great sense of humor.
  4. Kind, encouraging, and thoughtful.
  5. A great communicator.
  6. Not emotionally tied to ex-wife (still battling her and/or living in the past).
  7. Confident and secure with himself.
  8. A great father.
  9. Smart and successful (not in a monetary sense, but has a life purpose and enjoys his career).
  10. Maintains good relationships with family, friends, and his children.
  11. Is already divorced.*
  12. Loves baseball.*
  13. Accepts who I am unconditionally.*
  14. Exercises regularly and has healthy habits.*

* New additions over the last year.

Of the new items on the list, I have unapologetically added ‘loves baseball.’ I wanted to add it to the list originally, but felt that was crazy and close-minded of me. After dating some who did not enjoy baseball, I learned something essential:

Nothing on the list is crazy if it is important to me.

Do you or have you had a list?

How has it worked for you?





12 responses to “Dating Advice: Start with a List”

  1. That is a great idea. I have only dated once since my divorce and it lasted about a year. She was a great woman, but she was a horrible mother. I tried to ignore it, because it didn’t affect me (I thought) or my children, but I began to see how those qualities DID seep into other aspects of her life. I cringed every time she spoke to her kids and had a very difficult time keeping my mouth shut when I saw how they talked to her. I could just see her treating my future grandkids that way if we ever got married. Since she also was not good at communicating about difficult issues, she had to go. She was a good person and I loved spending time with her, but it would have been irresponsible to allow the relationship to go any further.

    I am going to go make my list right now.

    1. Naked Girl in a Dress

      I am glad this idea is going to be something you try. It really does make dating very simple. If you follow the rules, which I tend to ignore at times.

  2. I have had a list and been encouraged to ditch it because it’s too “limiting” — but my gut instinct says that I’m no spring chicken and kind of know what I want/need from a relationship. Why not articulate it so as not to waste time/energy on relationships that are obviously not long term potential?

    1. Naked Girl in a Dress

      It sounds unromantic, but it really is efficient to have a list. If you have a clearly-defined list, you don’t waste a lot of time on someone who is not going to be a good match for you. Keep your list!

  3. I’ll be 41 in just a couple of weeks. If something horrible should happen that I become single (again!) I think that I’d just forget about dating altogether.

    I like the idea of a non-compromise list. Having a focus like that can help, but is there a danger of the list becoming so specific that it will become next to impossible to find someone that fits?

    1. Naked Girl in a Dress


      Let’s hope you don’t need to make a list in the future!

      You have a point about making it too specific. When I first made a list, it was on the heels of a really bad relationship ending. There were many horrible aspects to that relationship and the first version of the list was what I should not have accepted in that relationship and warning signs (like no friends, bad relationship with family, unhealthy obsession/relationship with ex) that I ignored because I loved him. The list has gotten more specific after going out with lots of guys and realizing I needed to add a few. If I add much more, you are right; might not be able to find someone who matches up.

      Since I am incredibly happy with The Boyfriend (and he matches perfectly), let’s hope I don’t need to edit it anytime soon.

  4. David

    It’s a good list my friend. Of course, it really hit home that I hope I never have to make such a list myself. As much as being married to a “lady with issues” makes me crazy, being single in this decade would drive me to drink. More than I do now.

    1. Naked Girl in a Dress

      I have had some pretty crazy experiences dating, but it is entertaining as well. It’s funny what happens on a date–what people share, how they behave, what they think is acceptable. It’s worth sifting through when you find someone who is really great though.

  5. I had a list like that…I married someone who didn’t match ANY of my requirements and I have to be honest – it’s been a struggle. I adore him, but life would be a lot easier if I had stuck with the list!

    1. Naked Girl in a Dress

      I am sorry about the struggle, but happy to hear you adore him. That is a big part of making something work–the desire to do so.

  6. I started a list before I met my husband, and I stuck to it! And well, then I met my husband!

    My list was not only what I wanted in a partner, but also what I wanted from me in a relationship. My list for my own behavior kept me honest with myself and potential partners about my behavior and who I am.

    My list included guidelines such as “I will not make excuses for other people’s bad behavior,” and “I will be honest about my preferences when it comes to choosing what to do and where to go.”


    1. Naked Girl in a Dress

      I love the idea of creating a list for you as well. What a fabulous idea!