Scared of messing up... I've become a nervous teen again. *sigh*

[Leah33]

Why do most men have a harder time being alone?

[Batya33]

Yes, unfortunately, I have come to the same conclusion. Although I still think she is a very kind person brought up on the right values, her values have never been tested by real-life challenges. It is all very good saying that you don’t care about money, when you have literally never had to worry about not having enough to live your very comfortable lifestyle. Her head really is in the cloud and she has not considered very practical issues if we became a couple, like:

 

1) I could never buy her a gift that her father/brother/herself could not easily top.

2) It’s fine saying she does not expect me to buy things for her, but what about shared expenses like eating out, rent, hotels when traveling, flying business class etc. Either she would have to dial down her lifestyle, or pay for me, which would be very awkward regardless.

3) I don’t think her father would ever approve of me. I’m not personally successful enough, my family is not rich enough (albeit more educated).

 

As for the volunteering thing. No, I don’t think so, though she is quite generous to her friends. She actually got offended when I told her it was a bad idea to lend money (thousands of USD) to a friend who ran up loads of bad debt doing god knows what.

 

She recognizes the contradiction between her ideal to earn her own way in the world, and her unwillingness to sacrifice her lifestyle, and if I were brutally honest, her poor work ethic.

 

So in my opinion her values -which amount to words not actions -have not been tested by real life challenges because that is her choice. A person who has those values in a meaningful way would seek out opportunities to practice those values in real life, in real time. Lifestyles are not stagnant - people change their lifestyles all the time - I did when I got married, relocated away from my major city of 43 years and had a baby. From working in a prestigious company in a prestigious position and dining at lovely restaurants when I chose to to being unemployed, working around the clock at times caring for a newborn, then an infant, then a toddler where my spa day is when I got to go to the supermarket alone. Checking out sales and coupons not because we were struggling financially but because I was very aware that the income from my nest egg that I contributed every month (my choice, not my husband's request) was a fraction of my prior earnings. No more book club, women's networking group, professional networking events, parties at night. I absolutely embraced the change in lifestyle. I felt like I'd won the lottery. I didn't need to compare as I have done so here - I accepted all these mammoth changes with joy and adventure most of the time (sleep deprivation can hamper that lottery feeling or a toddler with an undiagnosed ear infection, etc). I chose these changes. Many others do.

 

Her lifestyle is her choice. She can make a different choice. And the whole "I can't top the gift" thing is absolutely ridiculous. My husband had a photo of us from our dating days embossed on wood for our 10th wedding anniversary. Who can top that?? He also bought me a lovely engagement ring. Who cares if someone else I dated could have purchased a bigger rock I absolutely wouldn't have wanted.

 

If she would feel she is "dialing down" her lifestyle to be with you instead of feeling excited then she's not the person for you. She's lending $ to people who don't actually need the money to survive -it's no big deal for her to do so and it's not generous because it's not a sacrifice for her.

[boltnrun]

Why do you dislike being "alone"? Do you feel not having a girlfriend means you are defective? Do you like your own company?

 

As for Jane, every date you take her on, every minute you spend with her and every message you send checking on her revives her hope. You are actually being more cruel by dragging this out.

[Leah33]

FTR, I hope my comment above isn't perceived negatively. If I was going to generalize I should have included women.

 

To offer a different perspective - I've been "alone" for the past several years by choice because I haven't had the head space to date and my heart was certainly not open to it. But, that's just me. Everyone's different.

[boltnrun]

Why do you dislike being "alone"? Do you feel not having a girlfriend means you are defective? Do you like your own company?

 

As for Jane, every date you take her on, every minute you spend with her and every message you send checking on her revives her hope. You are actually being more cruel by dragging this out.

 

Sorry, I thought the OP made the "alone" comment. I should read more carefully.

[MirrorKnight]

FTR, I hope my comment above isn't perceived negatively. If I was going to generalize I should have included women.

 

To offer a different perspective - I've been "alone" for the past several years by choice because I haven't had the head space to date and my heart was certainly not open to it. But, that's just me. Everyone's different.

 

I thought your comment was rather random tbh. Not sure where you got the idea that I have a hard time to be alone.

 

I was mostly single for most of my 20s, I would say largely by choice. I have ended two relationships in 2019 because I did not want to "settle" with women I was not "all in" on.

[Leah33]

I thought your comment was rather random tbh. Not sure where you got the idea that I have a hard time to be alone.

 

I was mostly single for most of my 20s, I would say largely by choice. I have ended two relationships in 2019 because I did not want to "settle" with women I was not "all in" on.

 

Then disregard my "alone" comment.

 

I think Rose Mosse's input regarding Lily is pretty spot on. Some women simply are not comfortable dating someone freshly separated and not divorced.

[Rose Mosse]

I think I recognize a pattern here too, if I am totally honest. I put too much stock in what people say, especially early on, and extrapolate too much. I misread Kathy's eagerness for a committed relationship for how much she cared about me, I jumped to conclusions about Lily's values without understand the context in which she expressed those values.

 

I need to focus on own self-improvement. I think Lily could have been a great match - if I had maintained the trajectory I was on when I was 19 or 20, and earning $100k+ annually now, as quite a few of my peers from then are. It's not that Lily is materialistic, she is much less materialistic than Kathy, but we just do not even share the same world.

 

It's ok. One thing at a time. Jane needs to go. She has to leave your place in the UK. No more phonecalls and visits, no check ups on you and no check ups on her. You're dating and doing your thing. We've all done that in odd transitions here and there but you might have to lower your expectations overall because it's a two-way street. As you're thinking about the person you've just met, she's also thinking about you and all the things that you've said about yourself while introducing yourself.

 

Lily seems foreign because of her upbringing but at the end of the day, I'd look for traits like trustworthiness, kindness, generosity, attention to detail, ability to recall and retain good memories more than bad memories (this is critical for long term! and goes back to that generosity of heart). She might have overshared with you the detail about lending her friend money. That's really her business to tend to and if she's young she'll learn eventually how to manage her own money properly. Her relationships with her family matter and if she's unable to temper those relationships or manage them with her parents for instance, it's not a good sign. You may also need to get a little comfy with the idea that your partner has her own income and access to funds independent of what you can provide for the household. It's a good idea to be on the same page with your values so I do see your concern too. On the outset you may see irresponsible use of money but on the other hand it can be viewed as generous if we don't know the full context or what the situation is like or who that friend is to her.

 

Maybe this is also a good way to explore whether you're comfortable with the thought of in-laws one day and the idea of a larger family, ideas about shared finances and other long term living ideals you may have. If you're recoiling for instance it may be a sign that you're not ready to be in a serious relationship.

[bluecastle]

Jane needs to go. She has to leave your place in the UK. No more phonecalls and visits, no check ups on you and no check ups on her. You're dating and doing your thing. We've all done that in odd transitions here and there but you might have to lower your expectations overall because it's a two-way street. As you're thinking about the person you've just met, she's also thinking about you and all the things that you've said about yourself while introducing yourself.

 

Well put.

 

At the moment, however you want to dice it, you are dating while still uncoupling with someone, emotionally and logistically. That is who you are, in rough outline, which is who people you meet right now are going to encounter, consider, assess. You're allowed to scrutinize others however you choose in terms of where you spend your own emotional capital, be it for being late or for a comment about Uber, but they in turn are likely to scrutinize you as a man trying to establish his next relationship before his last one is dealt with.

 

Some people are game for that, many are not. It's kind of the Catch-22 to going from a serious relationship to dating without inhaling and exhaling: you're limiting the pool of people who will take you seriously, while increasing your odds of connecting with people you struggle to take seriously. At the risk of generalizing, some of the very qualities that will allow someone to explore romance with someone in your shoes (ex living at his house, ex currently in town) are also qualities that you might find frustrating, from naivety to insecurity to an unserious attitude about romantic partnership. This is may be a moment of discovering exactly that.

 

Not saying that with judgement, but just to keep your expectations in check. Along the lines of what Rose said, this might be a good time to practice having an open mind about people, not worrying too fiercely or too quickly where it will all go, since you have some very real loose ends to tie up yourself until anything can sincerely take off. You're inherently asking anyone who dates you right now to extend an enormous amount of grace, so perhaps think of that as a reason to extend the same grace in return. It's a great muscle to build that will serve you well, not just in dating but especially once you're in a relationship again.