Lol.

Hmmm. Don't dig so deep into your own head on this.  They don't know. If they do, so what?

I think that when we worry about being alone, we are. Even when we aren't, We are to some level because we force things that may not otherwise occur organically.

I was at this impasse 30 years ago when DW and I were discussing getting married. I had decided no. I was not going to remarry.  Nothing to do with her. It was all me.  My dad gave me advice then that gave me perspective and ultimately put me on the path of making a life with my DW. His statement was that I was young (30) and I had a choice. I could either have a life with a series of partners or I could take another chance at making a life with someone.  Had I not been dating my DW when that conversation occurred I likely would have chosen the series of partners route.  DW was and is that incredible.

I find that when I am looking, I remain unsettled. When I am confident in me and am not looking, solid candidates show up in multiples.  At that point I find that I can fairly readily categorize them into dating candidates or more than dating candidates. I do not go down either list with an agenda. I let things progress naturally and adjust accordingly.

Start with the end in mind does not apply to this topic IMHO.  Start with a focus on ourselves and navigate the unfolding events from that perspective and the end will unfold.  Or more accurately, the adventure will unfold.

I forced it with my XW ignoring my gut.   With DW, it has never felt or been forced.  We just fit.

So, do you want to be a SM and reset a bit to engage with a person less mature in their career and their family status. Or... do you want to test drive a childless man with a more proven .... asset position, career, cultured perspective and interests?

How are you with each of them?  Are there any red flags or concerns. What does your soul tell you?

I have mentioned a very close friend who recently went through a very difficult divorce. She and her XH had been married for 30+ years. They were both just turning 50.  He got stuck in the Middle East during COVID and she was unable to join him as planned. That basically drove him batshit crazy. He became incredibly controlling.  He cut her off financially though he was the sole earner in their marriage at that time and had been for a number of years due to Expat opportunities that they chose to pursue together.  Her career went on hold due to trailing spouses not having access to emploment. Particularly women.  Interestingly, their dynamic was that she basically facilitated and guided his career. She is a highly recognized business consultant and motivational speaker. Extremely successful in her own right.  His career lagged significantly until they went Expat.  

They have been divorced for about a year and a half.  She is struggling. She wants a connection.  One of her coworkers is a nice looking similarly aged guy who is apparently good looking. She is beautiful.  He started stopping by her office, coffee, etc... eventually calling the visits his morning hug.  They also attended the same Church.  She was starting to give thought to him as a candidate.  At a Church event he was way touchy with several younger women and that freaked her out.   

Rather than go back to dynamic professional environments she works non profit cause focused organizations that are led by volunteer boards.  Several board members are intimidated by her because she is a rock star at organizational performance optimization and change leadership.  So, she is struggling with change. The divorce knocked her for a loop, the work hug guy shook her up, and a lady BOD member has a lady boner for getting rid of her because our friend has initiated changes that limit that board members ability to use the organization to give her friends and family jobs and do them favors.

Change is difficult. Even for top tier change leaders.

Be good to you, settle your soul, go the route that represents the lowest risk of upheaval in your life. Whether it is one of these two, or someone else, or no-one.  You do you.

You are who matters.

The Female Dating Strategy  podcast on Spotify lol. They are a bit nuts, but can be helpful for women who have been used and abused and are vulnerable to falling prey again or want to polish up their boundaries and the dating game. But make sure to listen to the first few, because afterwards it tapers off into time-filling and some real utter tosh.

 Also- for a more serious podcast that's not just about dating, but also figuring out oneself and what matters to you, growing helpful attractions and suffocating some useless attractions that we may have, check out Deeper Dating run by psychotherapist Ken Page. Also, the same as with the above - the first ten or so episodes before it becomes time-filler episodes.

I'm terrible at dating advice. If I didn't purely luck out with DH I probably would have ended up with a serial killer. 

Because you're single and no one has dropped down on their knee to take you off the market. You don't owe them anything.

Now for The Choice. I read in the past blogs and one seems to have a child, not sure how old. Try your best not to choose that one. 

Of course it would make sense that he's the candidate likelier ready to settle. I'm sure he wants stability for his child, as he should. But unless the BM has moved on, or is accepting of him moving on....it's honestly a difficult uphill battle. Also you have to see how his boundaries are and how he manages time between parenthood/personal time/time for relationship with partner. 
 

Obviously, I think me now would go for the travel guy who has his stuff together. See where his head is on commitment and if it would be something that aligns with you. I think a lot of times people become intimidated by other people, and fear giving it a true shot. Most people want to simply feel loved. To be seen, heard, and loved on. Give him a real shot and see where that goes. Even if it doesn't go anywhere, I feel that the one with the child has a bigger chance of still being in the dating market, and then just continue there if you want. 
I'm officially invested in this, so you better please keep us posted!

Worried about them finding out? This part is unsettling. It's only fair and reasonable that either one of them know that you are dating around. You're a grown woman and have every right to hit the dating scene and to do so in a way that's open and honest. Imagine you're really into just one and imagining your life long term and in your mind committing to this person only to find out that he has been seeing 6 women in a rotation and you were completely unaware, in the dark and thought he loved you but he was secretly juggling 6 trying to make up his mind. It would hurt and suck. I know that's an exaggeration perhaps but concept the same. When I was dating and finding my way it was clear and open information to anyone that I was seeing that was the case. The problem also with the dating scene and especially apps is the next shiny thing is literally at your finger tips. It's a total disadvantage. If we are always searching we will always be searching and single and looking for the next shiny thing. 
 

Just my perspective and opinion. I think you have to be honest with them both and then you have to just decide and work to build a life with one. I would guess neither of of the two are your IT if you don't have one that pulls harder. 
 

If you're simply having fun, keep having fun. Hell add more than 2 but do that part honestly with all involved. If you're looking for the one you're already off on the wrong foot I believe. 

Let's rephrase your statement "juggling two dudes" and change it to "dating two dudes."

Unless one or both of them has initiated the talk about being exclusive and becoming their girlfriend, you are a free agent.

For all you know, they are also dating other people. Even if you're sleeping with both of them, as long as you're taking precautions, you don't owe them anything.

I'm with whomever said don't pick the guy with the kid. He may be wonderful, but you're automatically adding complications to your life with a child and an ex.

Or the big favor trick.  Or some other thing.   Do these men have kids?   How do they react with there kids.  We don't want to go down that slippery slope again.  You need to get a good ideas of there relationship with their kids 

I'd be sending out feeler questions or "red flag" questions. That's how I would decide, lol. I'd be more picky now for sure. I have a lot of requirements now after ending up with at first a controlling narcissist and then a Disney, guilt ridden dad. I would probably be alone forever because of all of the things I am looking for. 

The one with the kid I would be wary of. I would ask what his relationship is like with his ex and if they have a court order for the child. (depending on age of the kid)Ask what their communication is like.

Ask if they've had major issues about coparenting (this is where you might get an idea...) you know all the things to look for as you've been through it all with the last Disney guy and also all the nightmare parenting stories on here. 

I would make a far different decision now than I did then.  Though if I was 30 again and met my DW, I would not change a thing.

You have navigated the blended family jungle.  Trust that experience and model your decisioning accordingly.  If the older, established, non parent plucks your strings and makes your heart hum, go with that.  The one is the one you can make the most fulfilling life with. No one knows how it all unfolds.  Unfortunately no one can know the details of any journey.  That is why I use what I refer to as the guided missle model.  If we wait for the perfect shot, we never go for it.  Things are constantly changing. If we see what looks like a good goal, point generally in that direction, take the shot, and adjust as events unfold.  The meandering path is where the fun is.

If my DW were one to want a forever home, in one place, and to imbed in a community, we would not have made it.  That she is a person who enjoys the ride and is generally flexible has been critical to us working.  In some ways I have some guilt that I have not been able to give her a one place stable home and life. But, we would not be who we are had that been our path.

At 60, my RADAR would be hyper tuned to indicators that potential mate is self reliant, not kid or GK immersed, and able to maintain a healthy but not highly involved presence in their Kidults and GKs lives.  More succinctly, someone living their own life and not vicariously via their family.

Definately not living local to their issue.

IMHO of course.

Stay single!  As Kate Hepburn once said: "A man (or men) in my life, not in my house."