5 Dating Mistakes I’ll Never Make Again

15 Oct

Nobody will ever accuse me of being a dating guru. I’m the most indifferent dater of all time, and I can’t think of many things that interest me less than going on a first date. This doesn’t mean my dating pool has been completely dried up; I’ve actually had a few serious relationships.

None of them worked out, but that doesn’t mean they were a complete loss. Each time one fell apart I managed to find wisdom among the pieces I was putting back together. What I’ve learned over time is that love isn’t about dating more, it’s about dating smarter, and that’s why I’ll never make these mistakes again.

Date a guy who is emotionally or otherwise unavailable.

Are you emotionally detached? Married? Hundreds of miles away? Currently serving a prison sentence? Still hung up on your ex? I’m not interested. If I’m going to be with someone I want to be with him. When someone doesn’t have the ability or desire to allow you into every aspect of their lives, you end up being second, third, fourth or even lower on their list of priorities. I’ve found myself feeling like a supporting character in my own relationship, and I deserve to have one of the two starring roles.

Give more than my 50%.

Relationships are like a high stakes game of poker between two people who are required to go all in. If one person doesn’t push their chips to the center of the table, the game cannot proceed. Not only does the game cease to be fun, but nobody is a winner. When someone is unwilling to do their part, what they’re really saying is that the relationship isn’t worth the investment of their energy and time. If it isn’t worth theirs, it isn’t worth mine.

Date a friend.

“But Jen, your partner is supposed to be your friend.” I believe the person should absolutely be one of my closest friends, but I will now only become their friend after I’ve begun dating them. I dated two guys I was longtime friends with; I despise both of them now. Being wronged by a guy you met on eHarmony is one thing, but being wronged by someone who knows you intimately is an entirely different beast. Add the fact that I’m losing a boyfriend and a friend at the same time, and I have a recipe for a four alarm emotional fire.

Try to be “good enough” for my relationship.

I always had this idea of what a girlfriend/wife should be: beautiful, funny, smart, feminine, successful, [insert a million adjectives here]. I see her as my antithesis, someone who wears heels while she cleans the house, and who throws parties that make her the envy of all those who know her. I am currently trying to outlaw pants with button waists, and I spend more time alone than most bridge trolls. What I’ve come to accept is that I have a particular brand of crazy that some fetishist out there is going to love one day. Instead of seeking out the person I need to become, I’m going to seek out the person who loves what I already am.

Not letting go when I know I should.

I let two of my relationships linger well after their expiration dates, and like spoiled milk, they left a bad taste in my mouth. When two people stay together through their insurmountable dysfunction, it becomes a race to see who can drive the other crazy first. I’m finally at a place in my life where I’m taking my overall well-being seriously, and I refuse to give myself or my partner permission to undo my hard work.

All relationships take work, and I’m not under any false impression that I’ll live out a Disney-esque romance with someone. I know we’ll disagree, and that there will be moments when compromise is necessary. Weathering a storm is possible if you have the right captains aboard the ship.

There is no blueprint for success in relationships, and what is right for one may not be right for another. The pleasure and pain of love lies in the lessons you learn while mapping out your own course. Right now I’m feeling a little of both.

69 Responses to “5 Dating Mistakes I’ll Never Make Again”

  1. Saturn With Earrings 11/01/2013 at 10:02 pm #

    I completely identify with some of these points. Emotional unavailability is one of the worst and so if giving more than your share; that takes a terrible toll on your self concept. I agree. But I dated a friend and well, yes it ended terribly and he hurt me in awful ways but we did learn to be friends again. It took us two years but we did it and I’m glad I did. He’s a brilliant friend. He’s just not the boy for me. I suppose you learn those lessons too…

    • Jen and Tonic 11/02/2013 at 5:30 pm #

      Emotional unavailability is the worst because, as you said, it messed with your self-concept. I also think that it slowly kills you over time during which you’re not totally aware that that’s what’s happening. Then one day you wake up and realize you’ve been alone in your relationship for a year and a half.

      I’m glad you and your friend were able to patch things up. I think it depends on how both parties act. I live with my ex-boyfriend now, and he is absolutely my best friend in the whole world. My other exes? Yeah, that’s probably never going to happen because they’re d-bags with little to no accountability.

      • Saturn With Earrings 11/03/2013 at 12:09 am #

        I understand that. It can be extremely ugly in as well. Being alone in a relationship is worse than hell.

  2. Exile on Pain Street 11/01/2013 at 9:26 am #

    So late to the game. Sorry.

    This excellent advice is not gender-specific. Both women AND men could learn from it. Did you have that in mind when you wrote it? Has someone already made this point? Well done.

    • Jen and Tonic 11/02/2013 at 5:28 pm #

      I don’t like to pick on one gender over another. I’ll never say, “Men suck! We have it so hard!” because I think there are unique problems each side has to face. Having said that, I think there are some universal rules that apply to us all.

  3. The Hook 10/31/2013 at 4:19 am #

    “Date a guy who is emotionally or otherwise unavailable.”
    Sounds like the main character in a best-sell, but critically ravaged book series…
    Great post, Jen!
    By the way, any man – or any woman for that matter – would be blessed to have you in their lives.

    • Jen and Tonic 10/31/2013 at 9:08 pm #

      Thanks, Hook. I’m laying off of meeting new people for awhile because I’ve got some things in my life that I need to address, and typically, the people I’ve gone out with have kind of messed that up. I can only control me so I’m doing the smart thing and taking a step back and living selfishly for awhile.

  4. Summer Solstice Girl 10/28/2013 at 12:44 pm #

    This is gold!

    • Jen and Tonic 10/28/2013 at 1:16 pm #

      We have all learned a few things the hard way!

      • Summer Solstice Girl 10/28/2013 at 1:17 pm #

        And this is true. Wish it weren’t the case. But at least, others can profit from your hard-earned wisdom

        • Jen and Tonic 10/28/2013 at 1:21 pm #

          Exactly! I wasn’t smart enough to listen, so I had to learn.

  5. Lindsey (Currie) Dubois 10/24/2013 at 7:16 am #

    Hello there! I appreciate this post very much… I really do. Specifically the part that talks about not striving to change yourself, but rather being with someone who loves you the way you are. Yes! I agree. I want someone who loves me as I am, as my whole self with all my awesomeness and all my not so awesomeness and who has the courage and staying power to not only evolve with me but by himself for himself too. 🙂

    Great post!

    Have a great day,

    • Jen and Tonic 10/27/2013 at 8:26 pm #

      “…and who has the courage and staying power to not only evolve with me but by himself for himself too.” That is so important! I think evolving with another person is crucial to the longevity of the relationship.

  6. Le Clown 10/18/2013 at 11:31 am #

    It is real easy for me: You think “I like Turtles” is funny? Then we have a chance. Even if you don’t wax.
    Le Clown

    • Jen and Tonic 10/18/2013 at 2:13 pm #

      “I like turtles” happened right here in Portland. There’s a whole city full of men and women who would be compatible with you.

  7. becca3416 10/17/2013 at 2:28 pm #

    I struggle with 4. I try to be perfect instead of just being. It’s a process, but I am definitely getting better at it. I’ve driven people away by being me, but I’d rather drive away 100 guys under the right pretenses to get to the right one than the other way around.

    • Jen and Tonic 10/18/2013 at 2:25 pm #

      You’re exactly right. It’s actually such a wonderfully different feeling when you’re with someone who “gets you” and loves you for the person you really are.

  8. DeeDee 10/17/2013 at 10:06 am #

    Fabulous insights, Jen – I think the “someone who loves who you are right now” point is extremely important. Most of the rest will sort itself, or is more of a “your mileage may vary” sort of thing. My relationship was sort-of long distance to start, but that was temporary and probably for the best (I was finishing up undergrad, he would have just distracted me on school nights!) not to mention it was obvious that I was top priority.

    But a lot of people enter into relationships thinking that they will change either their partner or their own self to make one or the other “good enough.” I’ve only seen that work out well once, and that was well into the relationship when the guy decided he wanted to be a husband and dad, and realized he needed to grow up a little for that to work – but remained the same weirdo we all loved. I think it was actually one of the most inspiring declarations of love I’ve ever seen, but again – that was well after they already loved each other as-is.

    Stick to your guns, Jen – you’ll find that someone someday, or else find contentment without, which is also a legitimate way to go. I didn’t find my sweetheart until I decided it was OK to be alone and stopped looking (he showed up almost immediately after that!)

    • Jen and Tonic 10/18/2013 at 2:18 pm #

      I’ve learned (the hard way) that you can’t change a person. If they care enough about themselves, and their relationships, they may change, but it isn’t something you should bank on.

      I’m at a place in my life where I want a ready-made boyfriend. I don’t need his baggage, his excuses, the hope of progress. I just want someone to talk to, who I can trust, and who makes me laugh. If it can’t be easy in the beginning, it won’t ever be easy.

      • DeeDee 10/18/2013 at 5:22 pm #

        True that! I hope you find that ready-made package deal – that would be a jealousy-worthy coup.

        Of course, when you find the right person, it pretty much really is just easy, even though someone else would find that same person difficult and annoying. Like my husband. A friend once told me (in her cups), “I’m so glad you found each other – you’re Special Needs people.”

  9. writerwendyreid 10/16/2013 at 8:02 pm #

    Wonderfully written post Jen. You go girl. xo

  10. The Bumble Files 10/16/2013 at 6:30 pm #

    I especially love your “Try to be good enough for my relationship” piece. Never let go of that one, Jen. You will find someone who will appreciate you and love you for you.

    • Jen and Tonic 10/18/2013 at 2:15 pm #

      I like to believe there really IS someone for everyone. I hope to find my someone one day.

  11. PinotNinja 10/16/2013 at 1:01 pm #

    Definitely, DEFINITELY, only date someone who is into the real you, both because the real you is awesome and because you can only hide the real you for so long. Plus, it comes in handy later. Whenever I bust out my special brand of crazy, my husband will give me a shocked looked. My response to that audacious look is, “Dude. Stop it. You knew what you were getting into 11 years ago, and you signed up. It’s time to lay in the bed that you made.” His only response is to shrug and wander away because he just had the truth thrown all over him.

    • Jen and Tonic 10/16/2013 at 5:44 pm #

      You’re totally right. I forgot there is a clause in marriage which says, “You saw this coming, and if you didn’t strap on your seat belt by now, that’s your bad.”

  12. sharlene777 10/15/2013 at 8:59 pm #

    Great words of wisdom JT, love it!

    • Jen and Tonic 10/15/2013 at 9:17 pm #

      So nice to see your face here, and I appreciate your kind words. I’d much rather be on a quest to find the right one than waste my time being with the wrong one.


  13. speaker7 10/15/2013 at 4:23 pm #

    I’m on board with finding the one who will love you as is. My husband readily accepts Hugo’s presence in our dining room.

    • Jen and Tonic 10/15/2013 at 8:43 pm #

      Your husband isn’t jealous of Hugo’s sex appeal? He must be a very secure man.

  14. persephone2013 10/15/2013 at 4:06 pm #

    Love your list. So glad I’m not single. Especially now that I’ve gotten older and get more and more picky the older I get. Fortunately, my husband keeps rolling with me as I evolve.

    • Jen and Tonic 10/15/2013 at 8:42 pm #

      That’s how you know you’ve found the right one. You grow and change, but do it together.

  15. rollergiraffe 10/15/2013 at 11:31 am #

    All good things. And a gift that you’ve learned them before making unalterable life decisions. I love how self-aware you are!

    • Jen and Tonic 10/15/2013 at 12:47 pm #

      Yes, exactly. Better to clean up a leak than a flood. And thanks for the comment on my self-awareness. Historically speaking, it hasn’t been my strength, but it’s something I’m working on.

      • rollergiraffe 10/15/2013 at 1:31 pm #

        Well if we all started out perfectly self aware and capable of making good decisions there would be no art, literature or hilarious blog posts.

  16. daniheart21 10/15/2013 at 10:15 am #

    Jen everything you said makes perfect sense and is good advice, but I think # 4 is especially important because when we try to be something we are not a relationship is destined to fail. 🙂

    • Jen and Tonic 10/15/2013 at 12:46 pm #

      Eventually the mask has to come off, and the other person is like, “Who the hell are you?”

  17. Ms. Roberts 10/15/2013 at 9:46 am #

    I have to say, after my stint with a married guy, I am very happy. I get to do whatever I want without him getting all mad or jealous. I feel a lot better about myself because people actually want to see me now. Big improvement.

    • Jen and Tonic 10/15/2013 at 12:46 pm #

      Life is supposed to be lived out loud, and you can’t do that when you are someone’s secret. A painful lesson to learn.

      I’m glad you’re in a better place now!

      • Ms. Roberts 10/15/2013 at 3:55 pm #

        “Life is supposed to be lived out loud”

        That’s why I am unashamed.

        Me too ❤

  18. Maggie O'C 10/15/2013 at 8:44 am #

    I would say #4 will always keep you balanced. Stick with that one and all the rest will fall into place. You sound good. Any time you want to untroll for a bit, gimme a shout.

    • Jen and Tonic 10/15/2013 at 9:34 am #

      You’re right. When we stay true to ourselves, we manifest a life that allows us to be that person freely.

      I’ll be organizing some Portland area thing in the near future, I’ll keep you posted!

  19. Madame Weebles 10/15/2013 at 8:33 am #

    Yup yup yup yup yup yup. I am in complete agreeance with these. I’ve made ALL of these mistakes. And there’s nothing sadder or lonelier than being only a supporting character in your own relationship.

    • Jen and Tonic 10/15/2013 at 9:33 am #

      In one of my relationships, I felt myself constantly chasing the spotlight, and sometimes acting out just so I could be number one. It drove the other person crazy, and me even crazier.

      • Madame Weebles 10/15/2013 at 9:41 am #

        I feel you. So much crazy. I should have just sent my therapy bills to my exes for them to pay.

  20. Carrie Rubin 10/15/2013 at 8:20 am #

    Excellent advice. I especially like the one about trying to be “good enough” for a relationship. When we do that, we’re not true to ourselves, nor are we being fair to our partner by trying to be something we’re not. In a relationship, we should strive to do our best, but not try to do be anything we’re not.

    • Jen and Tonic 10/15/2013 at 8:26 am #

      The best is all anyone can ask of us, and our best will be the perfect fit for someone some day. By focusing on trying to be something we’re not, we end up forgetting to shine a light on the really great things that are specific only to us. I need to remind myself of that quite often, and not just in my relationships.

  21. El Guapo 10/15/2013 at 8:00 am #

    tending to your overall well being should also be of extreme importance to whoever is lucky enough to be your significant other.

    (And you may have more luck in your campaign by forgetting the buttons and just outlawing pants.)

    • Jen and Tonic 10/15/2013 at 8:24 am #

      You’re absolutely right about that. Both people should be equally eager to make sure the other person is happy and healthy in the relationship.

      You also make a good point about the pants. I should start wearing nothing but my least ripped up pair of granny panties to speed dating events.

  22. michellestodden 10/15/2013 at 5:51 am #

    Agree completely, aside from the long-distance thing. But that’s only because I live in a shitty little town with zero relationship possibilities. Zero.

    Gotta move.

    • Jen and Tonic 10/15/2013 at 7:40 am #

      That reminds me of a show I saw advertised on television where they take women from a remote town in Alaska, and move them to Miami so they can find love. You need that kind of intervention You may want to give TLC a call.

      • michellestodden 10/15/2013 at 8:16 am #

        I’m crossing my fingers that sparks will fly in Austin. I mean, you never know, right? Right? Eh…. Maybe I will keep TLC in mind because I really haven’t had very good luck yet…

        • Jen and Tonic 10/15/2013 at 8:23 am #

          This is true! Forget Blogger Interactive, all my energy will be used to help you find Mr. Right. Or Mr. Right Now. Whichever you prefer.

          • michellestodden 10/15/2013 at 8:29 am #

            I want Mr. Right Now to be Mr. Right. Like for reals this time.

            btw totally completely unbelievably excited about Blogger Interactive. All giddy like a schoolgirl.

          • Jen and Tonic 10/15/2013 at 8:53 am #

            ME TOO. It’s going to be both overwhelming and amazing to see everyone in person.

  23. SocietyRed 10/15/2013 at 4:21 am #

    Holy crap Jen!
    You are the master, the rest of the world is Kwai Chang Caine.
    I can relate to every single word here but I could never put it down in such an understandable way. The poker example is my favorite but everything here is pure gold.
    And don’t worry, you will snatch the pebble when you are ready.

    • Jen and Tonic 10/15/2013 at 7:38 am #

      Just call me David Carradine.

      And thanks, Red. I think we all learn lessons as we go along in life, especially when it comes to matters of the heart. Some apply to the general public, but I believe we also learn boundaries that are specific to ourselves. I’m trying not to cry over spilled milk because at least I got something out of it.

  24. nobodysreadingme 10/15/2013 at 4:12 am #

    I have to say I’ve had some success at dating friends. I also had one absolute bloody catastrophe, but I still came out ahead overall.

    • Jen and Tonic 10/15/2013 at 7:34 am #

      I think, because I don’t make friends easily and have very few to speak of, that losing one feels like a huge loss. Maybe more than it would to another person.

      • nobodysreadingme 10/15/2013 at 7:43 am #

        I wasn’t encouraging you to change. As I was careful to say, I had one, no two disastrous ends to friendships when sex reared its ugly head. But yeah, some successes too.

        • Jen and Tonic 10/15/2013 at 7:47 am #

          Well, I think there’s a difference between having sex with a friend, and actually have a legitimate relationship with one. Perhaps that’s why the end to one of your relationships was a bumpy landing, and the end to mine were more like a fiery crash.

          • nobodysreadingme 10/15/2013 at 8:25 am #

            Any landing you walk away from is a good one, as pilots say.

          • Jen and Tonic 10/15/2013 at 8:27 am #

            I actually really love that sentiment, especially in this capacity.

          • nobodysreadingme 10/15/2013 at 8:30 am #

            I’m of that opinion too.


  1. What I Look In A Person or My Top 5 Dating Mistakes | Sincerely, Ms. Roberts - 10/17/2013

    […] Jen at Sips of Jen and Tonic wrote this incredible post about her five dating mistakes. The sad thing is that I have many dating mistakes. I was the sort of person that if I liked him or her that all systems go! Never-mind if they are still attached their earlier girlfriend or wife (!). Hey, if we love each other why does all that matter? […]

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