Lapsed

Dear Jewish Fairy Godmother:

I am not a particularly religious Jew, though Passover was always my
favorite holiday growing up, for the familial get together, the food, and
the story. I have no particular interest in attending services or
becoming more observant. But I miss the rituals and the meaning that
Judaism provided when I was young. Is there a way that I can address
liberation themes in my own life, without the full bore ritual of a
Seder?

Lapsed

 
Dear Lapsed:

Consider a Seder anyhow, because attending will have impacts you
cannot predict. It’s more than the historic story. So I would ask around
among your Jewish friends and see if you could get an invitation. It’s
pretty traditional, like Thanksgiving, not to let someone feel alone.
Either way, try asking these four non-traditional questions. You can
see if they work for you:

 

Question 1, Ask: What your special gifts are in this world. Why are you
here? What do you do for others? Is it your kindness, your intellect,
your willingness to help? Think about what makes you you. Write it
down. Name it and claim it.

 

Question 2, Ask: How could those gifts become a problem to you
through overuse? For example, if you’re a giver, have you failed to
learn about boundaries? Pay attention to when you use your gifts in
your daily life, and how you overuse them. Taking notes is good.

 

Question 3, Ask: How you resort to your gifts in time of stress and
difficulty. In a crisis, do you fall back on a core strength but fail to
energize other aspects of yourself? Do you always use your heart
when your head might be more appropriate to a given situation? Or is
it the other way round?

 

Question 4, Ask: How do you protect yourself with your gifts? For
example, if you’re always so smart and rational, do you forget to listen
to your heart when it might help more?

 

 

Get this far during Passover and see if you feel more liberated
afterwards. Change is hard and the spirit of the holiday is about
getting ourselves out of the narrow places and into a bigger world.

Second Fiddle

Dear Jewish Fairy Godmother:

I come from a big and generally loving family. The only time we sibs
(two gals, two guys) have problems is with competition, as in who
gives what gifts to parents, etc. But every year my sister tries to
upstage me at Passover. We have a family tradition of alternating first
and second nights. When she goes first she puts on such an
ostentatious display that my Seder feels small and average. She says
she cooks everything herself but I’m convinced she’s used a deli.
When she goes second she makes a point of outdoing whatever I have
done. It sounds petty, but if I make one dessert she makes two; if I
make two, she serves three. My brother is single and never has to
host. I know he loves us both, but he knows how competitive she is
and always compliments her profusely. It shouldn’t bother me but it
does.

Second Fiddle

 
Dear Second Fiddle:

Annoying relatives are one of life’s challenges. Silly or not, it’s clearly
gotten to you. A lifetime of sisterhood should have taught you that
you’re unlikely to change her personality. You could create a lot of
tension in the family by trying, but why? Instead, get into the true
spirit of Pesach and try to modulate the game. It won’t be as satisfying
in the short run, but in the longer one, you’ll be happier. Plus your
family will be more in tune with what the holiday is really about.
Bonus: if you master this lesson with your sister, other people will
have a harder time getting under your skin.

 
Passover is about liberation from mitzrayim. For the moment, consider
your personal mitzrayim to be a vulnerable ego and your sister’s
vanity. Since you’re not going to beat her at her own game, move the
goalpost. Instead of buying into perpetual one-upswomanship, strive
for simplicity, piety, and a hamish sense of family and warmth.
Compliment her for what she does well. Smile. Dig deep for sincerity.
Match it with your simplest best. Sparkle where it counts, from within,
and liberate yourself from this annual plague.

Motivated

Dear Jewish Fairy Godmother:

Last year four friends and I went on a diet together with varied results.
Predictably, the people who stuck closet to the plan lost the most, and the ones
who “simply couldn’t” give up certain foods did not do as well. In the interim, one
of the ones who most needed to lose (as in medically obese and more) has had
a variety of health issues. Her doctor told her to immediately lose 50 pounds and
then work on the next 50, with still more to lose after that. I agreed to support her
and go back on the plan, because my last 20 to lose are about as hard as her
first 50+.

 

Each day we check in about food, but for the past week she has
sounded increasingly off program, and particularly defensive about saying why
she “can’t,” “won’t” or otherwise is having problems and is modifying the program
to suit her. I started by saying, “What did your doctor say?” and then moved to
“You have to do what works for you.” But I suspect she is on the slide to no
progress. I want to be supportive but not derail myself in the interim. Part of the
deal was trading homemade food that conforms with the requirements of the diet.
What can I say or do, both to help her and to protect myself?

Motivated

 
Dear Motivated:

It’s always frustrating when people who most need to change refuse to
do so, especially when the people around them have rallied to support
them. In this case, you should let her doctor be the hammer, not you,
if you value the friendship. Start the conversation that you will need to
have with: I know you’ve been struggling with this diet. I’m not tied to
what you eat, or what program you choose to be on. We don’t have to
do the same thing. Maybe you should talk to your doctor about what
s/he thinks is a good way for you to lose the weight, because your doc
is more in touch with the specific medical issues. For me it’s hard to
hear that you are choosing to modify the plan, because I am doing my
best to stay on it. So let’s not talk about what we are eating or not
eating. Let’s focus on our successes and how we can support that.
Re the food sharing, say you should each text the other when you
make something that is available for sharing. As simple message like,
I made XYZ soup. Do you want some? Then the recipient can choose if
it suits her program. I suspect time will have more of an impact on her
health than any words you might say. Focus on your own.

Not Moneybags

Dear Jewish Fairy Godmother:

‘Tis the season of invitations and gift trolling. Many are for B’nai
Mitzvahs, which I recognize as an important rite of passage, though
some of these children turned 13 back in autumn, but apparently
needed the extra six months to learn the prayers and Hebrew. Some
are from colleagues for their children and others from seemingly
random synagogue members. The other half are about weddings,
which is a huge commitment and I honor (having failed myself). But
when I get an invite from second cousins in states across the country,
I feel more like I’ve been asked to contribute to the newlyweds’
coffers, and less like a valued relative. I‘m just your average middle-
aged, middle-class guy. I have family of my own that I support and
gift. What are the limits, beyond a polite No thank you?

Not Moneybags

 
Dear Not Moneybags:

Any invitation can be responded to with a polite note of No, thanks. I
wish you all the best, though it tends to be less blunt if accompanied
with some personal thoughts and good wishes enough to fill up a note
card. Only you can decide which of these to accept, but here’s some
baselines to consider, which can be augmented as much as you like for
people whom you genuinely love.

 
For B’nai Mitzvahs for children you do not personally know well, decide
on a book or two and give it with good wishes. I’d vote for something
about Jewish heritage, perhaps even a Holocaust memoir, and/or
something about Jewish values aimed at teens. You might even enjoy
sorting through the options. Then give exactly the same gift to each of
these young people, so there is no interpretive comparison.

 

 

For newlyweds, I give the same thing to each married couple, and you
are welcome to appropriate the ritual: a wooden soup ladle,
accompanied by a note about the importance of good nourishment and
nourishing communication as the key to a long-lasting relationship.
Again, for those you genuinely know and like, you can decide what
more is appropriate, even a cookbook or a stockpot.

In the Middle

Dear Jewish Fairy Godmother:

I’m caught between two feuding friends and unsure how to help reconcile them.
It’s not a shooting war, or even a war of words. It’s more like the Cold War in its
waning years: lots of snippy sniping comments, judgmental jabs, and (at least
from my point of view) a distancing that has become habit, instead of the habits
of confiding in one another, going for quick walks or coffee dates to catch up, and
generally feeling like the other is an ally, not a rival. To top it off, one is in a long-
term crisis with two members of her family having significant health issues (a
dying mom and pre-surgical husband), while the other just bought a new house
and got a promotion. I can see the stressed-out friend getting more and more
weary as she struggles and the on-the-rise one getting less tolerant and
impatient as she pursues her new and busy future. They both talk to me, and I try
to be a friend to both of them. Should I try to bring them closer together or let
nature take its course, whatever that is?

In the Middle

 
Dear In the Middle:

There’s a limit to what any third person can do to untangle two feuding parties.
But that doesn’t mean don’t try. Think peace talks in Ireland or truth and
reconciliation in South Africa. The only thing that matters is getting folks to talk to
one another. It’s critical that you NOT, repeat not, try to talk for either of them to
the other. You can listen, and you can make suggestions. But you should not
carry stories back and forth nor should you try and tell either of them what to do
or think.

 
Instead, you should talk from your own point of view, expressing to each
individually the sadness you feel seeing two people whom you know love and
respect one another being unhappy about the state of their friendship. To the one
who is up, express patience for the one who is down. For the one who is in
stress, ask what you and/pr others can do to help. Suggest that you all go out for
drinks, with other friends, as a way of normalizing some social time. And if all
else fails, just say, I think you two need to talk. This has gone on too long. I hope
they listen.

On A Roll

Dear Jewish Fairy Godmother:

I’ve been somewhat crazed and monomaniacal for the past few months working
on a big project. It’s the kind of thing that could make or break my career, so I
have had much less time for the hand-holding chit-chatty kinds of conversations
that I am often the one to initiate with friends. In general I am a caretaker
personality, and often give my friends up to 80% of a given conversation to talk
about their troubles. Now, while I have been gloriously optimistic and energized
(the external world notwithstanding), they have been struggling with all manner of
tsoris. In the past week two if them have snapped at me while I’ve been talking
about the upside possibilities in my future. How should I approach them to make
nice?

On A Roll

 
Dear On a Roll:

In a real friendship, people understand that sometimes the balance of
up and down, happy and sad, etc will fluctuate and be uneven. Most
friends are happy if their buddies succeed, and even grab onto the
coat tails of their joy and energy to help pull themselves out of a
trough. If two of them snapped at you it is a signal that you may have
crossed some invisible line, where no matter how attentive you have
been in the past, they simply don’t have the reserves to cope with
your positive energy now.

 
Take a little break from schmoozing till you finish your project, say a
week or so. Any attempt to mend the rift now will look self-serving and
even insincere. Then reach out and ask how each is doing and if
there’s anything you can do to help them through whatever their
immediate stress is about. If you really are a caretaker, you’ve
probably helped them in the past, so if they’re smart they will let
bygones slip away and say thanks and tell you how to be useful. At
worst, just go back to listening. If your project pays off, be sure to
start off with, Are you ready for some fabulous news from my life?

Overworked Mom

Dear Jewish Fairy Godmother:

I’m a middle class housewife who gave up her career to become a wife and
mother of three kids, now all thankfully in K-12 school. I have a precious five or
so hours each day to accomplish everything needed to run a household and take
care of myself. My husband changed jobs, and now travels out of the area at
least a week a month, so then the pressure doubles. A few years ago I started a
business selling essential oils with an online company that had a local rep,
assuming that once the littlest was in school I could get real traction. I started
fast, building a base of downline sellers and the rep loved and praised me. Now
everything has shifted and I have very little time. I know her income depends on
what I sell, but mine is more of a hobby business and I don’t want to feel
burdened by what I can’t do. How can I explain this without giving up the
relationship and the possibility for the future. I believe in the product and have
enjoyed the home shows I’ve done monthly. I just have zero time right now.

Overworked Mom

 
Dear Overworked:

When you join an online marketing company, as opposed to taking a traditional
job in an office, you do so assuming you’ll have a lot more control of your hours
and choices than if you have a boss and a desk you are obligated to sit in
specific hours of specific days. Your primary identity and commitment is to your
family, not to the rep of this company. Her income may depend on what you do,
but yours depends on what your husband does. Supporting him, the kids, and the
house is job one. You can re-engage with the marketing project when you have
more time.

 
In the interim, call or send her a message that says roughly: Dear Rep _ I’m sorry
my attention and sales have been lagging in the past while. There have various
and time-consuming transitions in my home, and they have taken priority for my
time. That’s likely to be true for the foreseeable future. So I plan to take a hiatus
for a few months from doing home shows or actively soliciting more downline
people. I will of course continue to mentor and support the ones I already have in
place. This is part of my future, but needs to move back a few steps in my
present. Thanks for your understanding. You’ll know what to do next.

Earplugs???

Dear Jewish Fairy Godmother:

My mother was diagnosed with a terminal disease three years ago. At the time
she was given “one to three” years to live. We all became very indulgent towards
character flaws that have been driving us crazy all our lives, especially one that
over the last few months of holidays was enough to taint many family gatherings:
She hogs all the air time. She talks, whines, blathers, opinionates, and pontificates.
She does not allow anyone else to speak for more than a sentence or two before
taking over the conversation again. I love her and don’t want her to
be gone. But this is driving a wedge in our family. Her new experimental
medication seems to be working so well that now the doc says she could go
another five years. I can’t. How can I tell her the rules have to change?

Earplugs???

 
Dear Earplugs:

Regardless of what you say, you will need to do it compassionately.
We’re all dying, but your mother is old enough (given that you have an
adult son of your own) that she lives with thoughts of mortality every
day, augmented by a terminal diagnosis. Sometimes people need to
hear their own voice just to reassure themselves they are still here. So
what may feel like an extra burden to you and your family is also part
of the process of being a kind person, and needs to be viewed through
that filter.

 
I’d counsel a one-on-one to start. Take your mother out for a ladies
lunch, in a nice restaurant where raising one’s voice would be very out
of place. Explain very simply that you are delighted that her treatment
is working and she will be among the living for far longer than the
doctors had originally projected. Then say, But I think that when we
were afraid we would lose you far too soon, we all got into some bad
habits, that for the sake of family congeniality I’d like to amend.
Explain that her current habit of dominating conversations has become
a social liability to you and other members of the family who are
beginning to shy away from time with her, the opposite of what you
and she presumably want. Suggest that she expand her social network
so she has other social outlets, and say you’re happy to give her tips
on being a good listener as well as a good talker.

 
Don’t expect her to be appreciative. She may even pull rank as your
dying mother. Continue to profess your love, and set up a cue word or
signal that you’ll use to alert her if she’s crossed the line. It will take
time, perhaps more than she has. So be kind.

Wannabe

Dear Jewish Fairy Godmother:

I am a teacher who is also an aspiring writer. I have a great idea for a series of
young adult novels, with a spin no one has taken before. I’m a good writer and
have coached others, but I’m having a hard time figuring out how to coach myself
to find creative time. I work five days a week and have a husband, house,
chickens, and volunteer work calling on my time. But I finally have a place to
write. Our son has moved out and I appropriated his room into my writing studio.
Everything is set up but the big blank is my big butt in the chair. Hellllpppppp!!!

Wannabe

 
Dear Wannabe:

Creative time has to be made, not found. There will always be a long list of things
ahead of it, that can be seen as daily necessities not the “luxury” that writing may
seem to others. If you want to make your dream come true, it will have to rise
higher on your priority list and you will need to work hard to keep it there.
Congratulations for making a place to work. Now make time to be there.
You need to pick a number of hours a week to do this, say 20 to start. I am
eyeballing 2 hours a day weekdays, and three each on weekends. That may
mean getting up earlier or staying up later, getting our husband to assume more
household and cooking responsibilities, giving up a volunteer commitment, or
other seemingly large schedule shifts. But once you put them in place and stick
to them for a month, they will become accepted routing. Go into your study with a
pot of tea and no phone or other distractions. Do not respond to anything except
the house on fire. If you cannot write, then plot. If you cannot plot, then do back-
story exercises for your characters. Make this book as important to you as your
family for the next six months. Then take stock of your progress. You’ll know
what to do next.

Not A Wallflower

Dear Jewish Fairy Godmother:

Three weeks ago I had a great first date. We talked and laughed and traded
stories. I think this is a guy I could seriously like. But we have made two attempts
to connect since then, and both have ended up with me sitting home wondering
what happened. We are both free-lance consulting, and quickly bonded on the
difficulty of scheduling when we have very little control of our deadlines. Both
times the plans foundered on his end, with less than a few hours notice the first
time, and multiple texts back and forth the second time. In the words of an
economist friend, “The transaction costs seem very high.” I’d like to like him and
don’t want to scare him off, but I feel like a conversation about how we interact is
in order. Is it too early to say, “Here’s what seems reasonable to me if we are
going to get together.”…? Both times I could have done other things and lost the
chance when he bailed on me.

Not A Wallflower

 
Dear Not A Wallflower:

Not at all. It’s not only not too early but very timely. Both of you are
used to selling your time for money, so the value of a missed
opportunity (whether it would have been another date or just
unencumbered time) should be very obvious to him as well as you. It’s
quite reasonable, the next time you actually connect (in person best),
to start a conversation that goes roughly like this: I’m happy to be
flexible when we connect, as long as it is mutual and reciprocal. I
respect deadlines, but not whims. If we have actual tickets or specific
plans, I need enough notice to find an alternative date. But if we’re
just meeting for coffee or a meal, I am usually accommodating. If it’s
habitual it will not help this friendship. But if it’s urgent, I get it.
BTW, I wouldn’t lead with that, lest it taint the date. But I would be
clear when you say it. With a smile.

Horrified!!!

Dear Jewish Fairy Godmother:

This is a 21st century question of etiquette. My son didn’t date much in high
school. After a long college romance he is now with a young woman I hope he
will one day marry. But that day and parenthood seem very far off. Yesterday he
got a text from a young woman he was in a local pre-school with, who is three
degrees of separation friendly with my future daughter-in-law. She (the neighbor)
asked him, literally, in a TEXT!!, “Would you consider being a sperm donor for my
partner and me? We married last year and want to start a family. I always
remember what a great guy you were so I thought you might be willing to spare
some of the secret sauce. We would love to start as soon as you say yes.” Your
column is several pages too short for me to expound all the reasons I am
appalled. They are 24 years old. They have no personal relationship. He’s not
ready to be a parent, or to give up a child. “Secret sauce”?! A text?!? On and on.
My specific question is this: I want and expect him to say No, or No!, or NO! I
know about it because he told his dad over the phone, with the intro “You’re not
going to believe who I heard from.” How should we respond to this bombshell?

Horrified!!!

 
Dear Horrified:

I’m with you on virtually every level. But neither of us was asked to be a donor,
so your question is the proper one, how can you be a resource to your son? And
the subliminal question as well: how can you ensure he makes the right decision,
as in No, thank you. I’m not ready to be a parent, and when I am it will probably
be with my future wife.

 
Your husband and you should schedule an in-person meeting if possible or a
Skype if not. Be sure you can watch his face and body language when you talk.
Ask him what he thinks his response will be. If it is No, your work is easy. You
can focus on communicating the answer clearly and firmly. If he is in any way
considering the possibility, start with the more serious objections, from their youth
to the legal issues and responsibilities, to the possibility that any future fiancé
might have strong negative opinions. If he thinks that being a sperm donor is
something he would consider in the future, encourage him to do so anonymously
or for a very close friend with whom he might have an ongoing relationship. Also
insist that if he is serious now, that he commit to several extended sessions with
a counselor and a lawyer to understand the implications of a Yes.

Jammed

Dear Jewish Fairy Godmother:

I am not a lazy person. I’m a respected astrologer (that’s not an
oxymoron) who donates the proceeds of an annual new year’s talk to a
local homeless shelter. I’ve been doing this for almost 25 years and
the talk gets lots of local coverage and has expanded to a two-day
event plus online sales. But this year I got massacred by the double
holiday and visitors and have not yet begun to research my talk, which
is in ten days!!! I generally give two beautiful handouts, one for what
each planet means in each sign, and a cruise through the calendar
year noting big transits or shifts, eclipses, retrogrades, etc. How can I
do in a week what I normally take almost a month to prepare?

Jammed

 
Dear Jammed:

My advice for you is the same as I would give anyone with a big
project and a fixed deadline: break it into small manageable parts and
focus completely on each one, in order. I don’t know a lot about
astrology, but enough to understand that there are major associations
associated with each of the planets in whichever astrological sign they
are in, as well as important events in the heavens like eclipses or
when a planet changes a sign or goes retrograde (a trick of our
different orbits). Make a list if everything you talk about by category.
Make the grids for the planets and signs. Make countdown clock in
hours. They get started.

 
Allocate a fixed amount of time for prep, to conclude two days before
the first talk. You’ll need the last minute readiness to practice, get
clothing and details like flowers and recording set up all finalized. Then
divvy up the time per category and sit down to work. Unplug the
phone and hide your usual distractions like books and games. Give
yourself regular breaks for coffee/tea and rewards like a phone call
with a friend or a walk. Every time you accomplish a section, enter it
into the pretty handout format and save what you have accomplished.
Step by step, inch by inch, bite by bite. That’s how you’ll get to goal.

Momma

Dear Jewish Fairy Godmother:

I have been deluged with all things holiday. The confluence of Hanukah and
Christmas this year seemed to consolidate stress rather than spreading it out. So
when my future daughter-in-law (age 23) asked me to take her dog to the vet for
her because her boss needed her. My first thought was Aaarggghh one more
thing! But it allowed me to spare her a $1,000 bill for an ultrasound that showed
her ten-year-old companion lab (an amazingly sweet docile boy) has terminal
metastasized cancer. That explains his recent listlessness. The vet said he might
last three months, with or without a several thousand-dollar surgery. I think it is
time to say a sweet goodbye, and the money would be better put towards their
down payment on a house. But she is heart-broken, and in the spirit of the
holidays I let her make a bad decision to go ahead with surgery. Now I am
thinking that perhaps I should quietly tell the vet to slip the pooch a needle and
say that because he died during the operation she would charge only a minimal
fee. It feels both right and wrong to me in a confused emotional mess. Can you
help?

Momma

 
Dear Momma:

You’re trying to spare your future daughter-in-law the sorrow and pain we all go
through when we have to say goodbye to a beloved companion. You’re also
attempting to impose adult values on a girl who is new to adulthood. Being a
homeowner is as mythical to her as a large debt or losing a companion she’s
known since her Bat Mitzvah. You can’t transplant your sense of the world onto
her any more than you can expect a vet to violate ethical standards. I know you
want to make this go fast and have it go easy on her, but you can’t spare her
pain now or in the future.

 
Give her a cup of tea and a strong drink and sit her down to talk it through. Ditto
with your son, who seems absent from your note. Talk about the options, and
then respect her decision.

Other Side of the Fence

Dear Jewish Fairy Godmother:

We had a terrible storm in my area a few weeks ago. I had
massive debris on my lot. Trees down, some up to 60’ tall. It
is a difficult lot to access and it would have saved me
hundreds and hundreds of dollars to be able to access my
back yard though a neighbor’s drive and orchard so they
could pass brush over our fence instead of hauling it all
around the house. The neighbor said no, and chased off my
helping crew with an actual gun. Now I hear that his mother
has died. Normally I would write a lovely note, drop of a
casserole, and ask what I could do to lighten the family’s
burden. But I am angry as well as annoyed. Can I just slip a
note in his mailbox and be done. Or to I have to be more
neighborly than I feel?

Other Side of the Fence

 
Dear Other Side:

Good fences apparently don’t always make good neighbors.
Ultimately your neighbor has the right to decide that
damage to his orchard outweighs your costs to clean up. It
may be un-neighborly but it is well with both legal and
horticultural boundaries. I’m sure you are annoyed but at
some point letting go of your anger will improve not only
your relationship but your attitude towards life.

 
Losing a parent changes people. Do what you would
otherwise do. Write a personal note with an anecdote or two
about his mother. Perhaps cite some act of generosity,
though not too blatantly in contract to his actions. If you
don’t want to cook for him that’s understandable. Go to the
market and pick up something easy, even a pie, and leave it
on his doorstep with the condolence note. Then go about
your business. Also, start a list, if you don’t already have
one, of atonements to make next Yom Kippur. Put your
neighbor on it. Forgiveness is a much lighter burden to carry
than anger.

Not Miser

Dear Jewish Fairy Godmother:

How do you suggest dealing with a significant inequity in
income in a dating situation? We are both middle-aged and
started out life with a similar middle-class trajectory: stable
home, college, even both taught (me math, her English)
though not on tenure track. Then I went into business and
made a good living after risking a significant part of my then
life savings in a tech firm that did well. I’m not a millionaire
but I have a nice home and can regularly eat in restaurants,
go to theatre, etc. But my love life was not successful and I
divorced twice, both non-acrimonious and each ex happily
remarried.

 

Now I have met a woman I think I could very
much enjoy. But she is poor as a proverbial church mouse.
She says she lost everything in the recession, but there are
big holes in the story she told me. I haven’t pressed. I don’t
mind treating her when we go out (my generational
training). But I am reluctant to set up a pattern of paying for
everything to keep her life afloat, though it is clear that she
would be less stressed with an infusion of cash. I don’t think
I am ready for marriage, but I she’s the most fascinating
person I have met in a decade. Is there a middle path I can
walk for a while?

Not Miser

 
Dear Not Miser:

You don’t say how long you have been dating, but short of
an actual proposal, engagement, and wedding, I’m cautious
about suggesting you undertake large financial
entanglements. Many people suffered in the recession and
lost a lot. Teachers were probably already more vulnerable
on the financial food chain. But you cannot rescue them all.
Financial inequity in a relationship almost always becomes a
source of stress between couples, dating and even married.
Some work it out with various cost-sharing plans. Others
ignore it. But biting your tongue now is not a good recipe for
a long term balance.

 
I would do two things. First have a serious conversation with
her about money. Say you’re concerned by her past but
want to hear her history and really understand. Then say
when you go out on a date you are happy to pick up the tab.
That means meals, tickets, and various treats. But that you
are drawing the line on actually lending money. If that’s a
deal breaker, she will search for a more generous date and
you will lose her. Only you will know if that is a bigger loss
than money.