How can I trust myself to pick the right guy?

Over the past 5 years, I’ve been on tons of first dates. More than any person would ever want to, I’m sure. I kept going on first dates though because I was ‘picky’. I needed a palpable connection and a list of criteria to be met. It was meaningless first date after first date when I finally met my long term boyfriend.

Finally, someone I just connected with. The beginning was easy, I felt alive, and he was good to me. I finally picked the right one! Even his mom was excited about our future!

But time passed and he stopped treating me right and eventually he became my ex. I should have left a lot earlier than I did and now it’s hard to trust myself. 


I’m really picky and I still didn’t pick the right guy. How can I trust myself now?


I’m wondering if I should go about picking partners differently now since clearly, I’ve been getting it wrong all these years. I don’t think I’m too picky honestly, but however I am picking must not be working. Do I need to stop putting so much weight on that feeling of connection?

Maybe with the information I knew at the time, I was picking right? And eventually as time goes on, someone who was right for you can stop being right for your future.

We all know love has a way of blinding us so maybe I need friends and family to pick the right match for me. People who know and love me and have my best interests at heart. But we probably all know someone we would have picked differently for and who’s to say that they made the wrong choice?

Maybe with the new lessons I learned from my dating experience, I will pick the right one next time and I can trust myself. I can trust myself by being self aware. By knowing I’m a hopeless romantic and where my weak spots are. By listening to red flags when I first see them and by understanding the type of men I gravitate towards.



  1. Totally feel your pain and hardship in this. Just be even more grateful at this moment that you didn’t get married and have to deal with all the ugliness of divorce as well.

    I know for me, I do need to go all in on the feeling of a deeper connection. I’ve done the good and safe choice twice and unfortunately, good and safe never seems to evolve.

    What we need is someone who is willing to grow with us and challenge life together. One day, we will find this person whom is the right fit.


  2. Don’t be scared and don’t over think it! No matter how picky you are you will still pick a guy with flaws. We all have them, but if he is talking down to you, cheating, over protective and has poor restroom etiquette then let him go. (Just to name a few)


  3. I totally relate to this! My current boyfriend, who is totally the guy I see myself living out my life with is definitely not the guy I would have pictured myself with! I always thought I’d be with a guy from either New England or NY, works on Wall Street, has the same values as my family, and is a huge Rangers fan. Then I started dating this guy on a whim because he bought me an Angry Orchard at a Twenty One Pilots concert and kept giving me food and here we are almost two years later with two bunnies and a dog. I was talking with my friend the other day about it because she just broke up with a guy that on paper was perfect and could provide the life she wanted but on paper my guy is not the guy I wanted but ended up falling in love with and making me love my life. Go with the flow, you may find someone that’ll surprise you. And if not, every relationship is just another lesson in learning about yourself and your own needs!


    1. That’s so interesting! I’m glad you took the leap with your current boo! You make a great point that just because someone is what you want on paper doesn’t mean they will be the right one for you. So much food for thought, thanks for sharing!


  4. Before I comment on anything I’m going to preface with my own experience. I’m a single father of a young boy with full custody. I’ve tried dating over the past few years with horrible experiences. At the moment I’m resolved to not date for quite some time, focus on being a better father, and pursue my doctoral studies. I’ve also come to accept that no woman my age will accept my son. Most women around my age have already done wonderful jobs as mothers and are not seeking another child. It’s a well-deserved feeling.

    There’s some truth to what you express here, regarding someone being right in the moment, but not fit within the scheme of a future or lifelong journey. However, the part that always catches me about that is the word “journey.” While my fiancé was alive (she died in 2016 and we were friends for nearly thirty years) I was resolved, loyal, and committed at her side. We not only experienced an immediate connection, but we found ourselves evolving and changing together. For us, I feel a part of that recipe had to do with accepting the other person who they were at any given time. It didn’t mean that we always agreed on every little thing, but we resolutely accepted one another in full. I doubt I’ll experience that again in this life.

    I’m not one to believe in “lists” or some concoction of the right person. No one is going to be an exact match for any array of criteria I come up with on a given day. I accept that – if there’s a mutual attraction – there will be differences and quirks that come along with the entire dynamic. I feel that’s that a part of the journey together. Getting to know that person, being genuinely interested in what makes them uniquely who they are and cherishing that spirit.

    There’s also that issue of “red flags.” I’ve learned over past few years to head such things about people. I never had before. I was always extremely welcoming and that sometimes ended pretty poorly. However, some red flags can simply be obstacles to overcome together. A part of growing together, I feel, is overcoming hurdles with that special soul. I don’t expect any potential, lifelong partnership to be especially rose-filled all the time. There will be ups and downs. I’ll make mistakes and so will she. I see it as my role within a relationship to do my part, admit when I’m wrong (or have wronged), and be willing to make amends when I’m able. I only ask that the other person be willing to make a similar commitment.

    At any rate, you’ve given me something to think about for a while – at least until my son is in college, lol!


  5. Don’t set high expectations. Just accept that people will all have flaws. Be patient. Accept them for what they are. In the end, you don’t have to look for Mr Right. He’ll find you!


    1. I actually think i was accepting too many flaws with my ex and had to realize that the person they are is not the person i want to have a future with. You make a lot of sense though. Too often we set high expectations!


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