Category Archives: Dating

Uninspired

Dear Jewish Fairy Godmother:

I spent three years in a bad relationship in which my now-ex cheated
and lied so often that even when we were making up I think both of us
felt like actors in a bad play. I finally realized I am worth more. After a
year of counseling and not dating, I decided I was ready The first guy I
met, whom I told I did not want to date exclusively, texts me several
times a day, and generally acts adoring but never takes me out on a
real date, just invites me to his place “for a movie” which translates to
making out. The second guy I met is his opposite, very shy and almost
too afraid to make a move. He’s nerdy and sweet but we don’t seem to
have enough in common. Despite this, he invited me home to meet his
mother, which felt much too fast. I’m feeling very:

Uninspired

 
Dear Uninspired:

If you have two guys pursuing you my bet is that others will too. It’s
hard to turn down birds in the hand, but the bushes are full of men
who aren’t right for you, and you’ve failed to convince me that either
of these guys is even close to being “the one.” That said, number two
at least seems to treat you like a person of value. The first guy sounds
like a jerk, and I think you should clear his slot for the as yet unknown
number three.

 
Sit yourself down and inventory what you want in a good date and a
good mate. They may not be the same things, but be honest with
yourself and get clear on what the differences are. Then make a list of
non-negotiables, things you won’t put up with, no matter what. I’d like
to assume that means no abuse (physical or verbal), rejecting
someone who expects you to pick up the tab all the time, and avoiding
other horrors you’ve already suffered through. No matter what, don’t
compromise on those. Look for someone who has your list of wants,
and know that you might need to test out numbers three through
three hundred before finding who you truly love and deserve.

Nanette

Dear Jewish Fairy Godmother:

Do you have advice for how to graciously fend off a persistent suitor?
He is everything I am supposed to want in a date, but I find myself
putting “shields up” whenever I am around him. There’s nothing
specific I can put my finger on that should make me feel this way, but
it is consistent. The more I say no, the more he tries to woo me with
invitations or appearing in places that I am. It is not stalking yet, but it
feels like it. Short of being abruptly unkind, or threatening him with a
court order, is there a No, No, No that will work?

Nanette

 
Dear Nanette:

Yes, Yes, Yes. But here’s the rub: If you seriously want to get through
to Mr. Clueless, you are going to have to be firmer than you have
been, and risk his ire. If you are willing to be less polite you can
accomplish this. Decide that first.

 
When you are ready to go, plan a multi-pronged approach. Send him a
note that says, I am flattered by your attention and have seriously
considered whether I want a social relationship with you. The answer
is No, I do not. Please stop asking me out and trying to be in places
that I am. My answer will not change. Thank you for respecting my
choice. Then share the note not only with your own friends, but ask
them to convey the message to his friends that he is making a fool of
himself and that there are lots of other fish in the sea, as my mother
used to say.

 

Ask your friends to serve as allies in situations where he
tries to come near you. They should stick to you like glue, or be in
close enough range that if he does approach you directly (which most
people would stop doing after your note), that they can insert
themselves into the situation. If he does ask you out again, and they
are present, you should just say No, and they should say, in a slightly
louder than polite voice, What part of No don’t you understand? It
shouldn’t take more than once or twice to deter him. But if it does not,
talk to an attorney about what your rights are to request a restraining
order.

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.

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.

Just Friends

Dear Jewish Fairy Godmother:

Several years ago I met someone on line that I was attracted to but he was not
attracted to me. Over time we became friends. Even though he lives an hour or
so away, we would get together occasionally for supper or a movie. I got to know
a lot more about him as a friend, and learned enough to know if would not have
been a good relationship for me. He needs a level of emotional caretaking that I
cannot provide, and has some deep-seated issues that, while he is working on
them in counseling, would become flash points in an intimate relationship. This
weekend, while we went out on a rare Saturday evening, he was the perfect
gentleman: opening car doors, insisting on paying for everything, and then sake
in an offhandedly joking way, “I haven’t been on a date in so long!” I playfully
replied “Oh Baby” and we hugged goodbye as we do. Now I’m wondering if I
should say something to forestall some change in his mind about who we are
together, or just wait it out. What say you?

Just Friends

 
Dear Just Friends:

I think you wait it out. He could have just been feeling lonely and/or
playful or thought you were lonely. Sometimes it’s nice to take
someone out and be a gracious host(ess). Perhaps he came into a
windfall and wanted to make you feel special. Unless he follows up
with specific romantic intentions, e.g. moving in for a kiss, or starts a
conversation about the mistake he made a few years ago by not
getting involved with you in a real relationship, simply steer clear of
that territory.

 
That doesn’t mean you shouldn’t have an answer on tap. If anything
happens that is overt, look him squarely in the eye and say, I love you
as a friend, but I don’t want to change how we relate in a big way. I
was sorry back then, but now I think we are in a good place, and the
right place, with one another. I hope the friendship continues as it is.

New Again

Dear Jewish Fairy Godmother:

Don’t laugh at me. I am 67 and haven’t been on a date in years. I have been
happily single for a decade, and the few relationships I have been on emerged
very naturally from friendships and then ebbed back into same, after a lovely and
satisfying interlude. But now I said yes to an actual coffee date. It’s not just “out
of practice,” because I don’t think I ever was in practice. What does one talk
about? What should one not talk about? Are there unspoken rules of etiquette
that other people know but I somehow missed? Should I “just be myself” or is it
more important to create a good impression and let all my flaws come out later,
more naturally? Other than saying “No thanks, I changed my mind.” Do you have
any good advice?

New Again

 
Dear New Again:

This may sound silly or too simple, but here goes. Don’t think of this
as a date. Yes you want to get to know the other person, and the
other person wants to know you. You’re both in the “business” of
buying and selling. So that’s four personalities/observers sitting at the
table, all of them busy taking notes and listening for red flags like, All
my exes sponged off me. Or I don’t understand how anyone would be
married to someone who______.

 
It’s fine to display preferences and personality. Try to keep your
stories short and both informative and interesting. Don’t hog the
airtime and genuinely listen to what you are being told. See where
your interests converge or diverge. Don;t worry about remembering all
the names and dates but listen for big arcs of story, like cities lived in,
professions, marriages, home ownership, and children. You can always
go back and ask for details if you get to date number two. Most
importantly, believe what you are told. If a date expresses a history of
infidelity or bankruptcy, take note. Ditto for good works or personality
traits you seek.

 
Allocate two hours for this exercise, but ask a friend to call or text you
about an hour in, with an ostensible emergency. Then if you need to
flee, you can have an excuse. But use this only if it’s really really bad.
You’ll know if you want to get together again.

Thin Line

Dear Jewish Fairy Godmother:

Recently a friend in another city fixed me up with someone who lives
near me. The friend knew both of us who lived here and, after
checking appropriately, gave each of us the other’s contact info
suggesting that we meet for coffee. We did and hit it off, and are now
starting cautiously to date. Both of us have been getting emails from
her saying “How’s it going?” etc. I know she wants me to confide
in her but of all the people on the planet she’s the last one I would talk
to about a dating situation gone bad (or perhaps even good) because
she already has a close relationship with my maybe about to be honey.
How can I deter her politely but firmly, because I am appreciative and
do value the friendship.

Thin Line

 
Dear Thin Line:

Grown ups don’t act like 7th graders. If there really is an incipient
relationship, that’s wonderful. You should certainly say Thank you and
let her know how much you appreciate the connection. But you are
under no obligation to make this friend your confidant, and especially
to assume that anything you say to her would be kept confidential.
It’s fine for her to ask how it’s going. And it’s fine for you to say that
you’re enjoying the connection, look forward to more dates, and hope
it deepens into a relationship. But that doesn’t make her a messenger
to relay that. And you should be explicit saying that you want to be
able to talk to her without anything being repeated. Even having said
that I would urge caution. If you need someone to talk to about
intimate or personal things, perhaps better someone who doesn’t have
skin in the game and who hasn’t tried to push her way into the
conversation.

Sweet Tooth

Dear Jewish Fairy Godmother:

I’m single. In fact I’m a single lesbian, though many of my friends are
straight women and, over the course of time, their husbands have
become friends. We gals get together every few months for brunch or
happy hour. The guys don’t tend to socialize on their own, but we all
get along at birthday parties and holidays. One couple invited me to a
late summer BBQ and said, It’s going to be all couples so feel free to
invite someone. In the past I have sometimes brought along women I
am dating, if only to get a thumbs up or down from my buddies. But
now I’m flying solo and liking it. That’s what I said in my rsvp, which
netted me an Oh. Should I invite someone, go solo anyhow, or
demur? For what it’s worth the hostess’ hubby makes the world’s best
peach pie. It’s worth breaking all diet rules to have some.

Sweet Tooth

 
Dear Sweet Tooth:

I have a bias against people who discriminate against single folks. The
world is made up of lots of singles who are looking as well as lots of
singles who are happy being single. I’m assuming you have no
predatory intent on the hostess or her husband, other than perhaps on
his peach pie. Ditto for any of the other attendees.

 
Unless you have a current prospect, I would go on your own and have
a great time. Talk to anyone and everyone and enjoy the food, drink,
and festivities. If people ask about your love life, say you are happily
between relationships and don’t want to dabble unless it’s true love.
You can follow it up with, If you want to hear my list of what I’m
looking for in a potential date, just ask. Most people will, if only to be
polite. And you can add, I’ll gift you with a [hubby]’s peach pie if you
find me the right gal! You never know who knows whom. And you’ve
sweetened the pot for their sweet tooth as well.

Almost Dry

Dear Jewish Fairy Godmother:

This is a dating saga. I met someone on Match a year plus ago. We did
a lot of emailing as he was relocating, no joke, from Alaska to Florida.
He warned me that he would drop off the map for a while as he drove
through the lower 48, but I did not expect that to take a full year. The
emails stopped cold and he never called me, even though I had
provided phone numbers as well as my email. We bumped into one
another at an arts festival where coincidentally we both knew and
collected the same artist and started talking at her booth. That led to a
few dates and I could be interested….except…..he drinks a lot. And I
don’t mean just more than me, because I am a lightweight. But he
drinks more than anyone I have ever seen, and that includes my
alcoholic uncle. The booze doesn’t seem to affect his ability to hold a
conversation but I find it worrisome. Is there a way to discuss this
without immediately ending the possible romance?

Almost Dry

 

Dear Almost Dry:

You can have the conversation over tea or over drinks. But from what
you are describing, do not expect your potential beau to be
enthusiastic or even accepting about your concerns.
I’d begin by asking what role alcohol has played in his life and his
family history. You can preface it with your observations about the
difference in your respective intake. Don’t worry about alarming him
because simply insisting on the topic will raise his defenses. Be clear
on what matters to you. First and foremost, that he not drive after he
has been drinking. That mean with you as a passenger or on his own.
If he doesn’t understand that issue, then don’t bother with the rest of
the conversation. If he does, go ahead and speak your piece, and then
see if there is common ground to work with. But unless you have
already fallen so deeply in love that you’re going to see this through
no matter what, my money is on a short-term romance at best. Better
that than dying for love.

Single and Only Sort-of Looking

Dear Jewish Fairy Godmother:

I just got asked to join a “meet up” group for single adults over 60.
One of my friends, actually an ex, is hoping to have new alternatives
for dinner and movie excursions etc. The idea is to post “I want to do
X, Y or X at a certain day/time. Does anyone else want to come?” I
very much prefer one-on-one to group activities and also value my
time and whom I spend it with. I mostly want to have friends but
would consider dating if there’s a click. Ironically the same person
caught both our eyes. What’s the etiquette here?

Single and Only Sort-of Looking

 

Dear Single/Looking:

As tempting (and childish) as it is to “call dibs” on the prospective
datee, that’s not how adults, especially those who’ve been around the
block for decades, conduct themselves. Agree upfront that you will be
honest with one another, and that you’ll stay friends regardless of the
outcome.

 
Like Solomon and the two mothers who covet the same baby, you’re
each going to have plead your case, not in so many words but by
being a charming date.. If the friendship is worth its salt it won’t
matter if the object of your affections chooses either or neither. Flip a
coin to see who invites her to dinner first. Be very clear on this quasi-
date that while you’re looking for friends, you definitely would like to
know this person better because if you “met the right person…..” Be
clear about your relationship history and see if that level and topic of
disclosure is reciprocated. It is critical that you speak only well of your
friend to the date. Don’t be sly or coy. End by offering your contact
info and say (assuming it’s true) that you’d like to connect again for
fun and food. Then the other friend does the same, leaving it up to the
date to decide which, if either of you, gets the next chance to connect.

Momma

Dear Jewish Fairy Godmother:

I’ve read your column for a long time and I don’t recall anyone asking
you this before, but here goes: Can you write a singles ad for my son?
I know you don’t know him but here’s the bottom line. From the
outside he looks like an overweight (60-100 lbs), very shy guy, who
has a co-parented toddler with his ex (they finally broke up). He
watches too much TV in his room. The upsides: He does have a steady
postman job, and is incredible sweet and very funny, in a dry kind of
way. But first impressions aren’t what’s going to get him a gal. Do you
have words that might bridge the gap?

Momma
Dear Momma:

Because singles ads are a doorway to dates and first impressions,
you’re walking down a less likely path. I’d counsel that he get out of
the house more, when he’s not working. Even joining a
divorced/singles parenting group would be a great start, so he would
be among people who understand what he’s doing through with his
child, and he would be in a setting where people are there to listen to
one another, not reject them based on a single date. Ditto for taking a
class in something he cares about, even if it’s about popular culture, at
the local community college or parks department. People tend to perk
up when they are engaged with things they care about. They look
happier and are more appealing.
If you are determined to go the ad route, try something like this:
Sweet single dad looking for a woman who doesn’t judge a book by its
cover. I’m intelligent, funny, and have a great job and a great toddler.
I love TV and movies like X, Y, and Z. I’m also hefty and a little shy,
but loving, loyal, and very appreciative of the right person in my life.
Use a photo in which he is cracking a smile.

Ambivalent

Dear Jewish Fairy Godmother:

Can you help me with the “Let’s just be friends.” conversation? It’s not
that I want to end a relationship, but that I don’t want to restart one. I
was in a six-month relationship last year that started with a bang and
ended with a whimper. The details don’t really matter, but we both
concluded that we could have a good long-run friendship but that we
weren’t really in love with one another and that while we were great in
bed, that wasn’t enough to build a strong relationship upon. The
break-up was mutual and has lasted five months. In the interim she
got involved with someone else briefly, that apparently made me look
like a much better prospect. In the interim I have been single, and
reconfirmed that I really like living alone and not being in a
relationship, or at least not being in one with someone with whom I’m
not really in love. We went for dinner and movie yesterday and her
subtext was laden with “Wouldn’t it be nice to get back together, at
least as lovers….” At least a half-dozen times, and more like double
that. I just let them slide off, but I know the conversation will return.
I’m not averse to the idea, but know that it’s not what I really want in
my life, though with her it could be a temporary thing again. What
should I say?

Ambivalent

 

Dear Ambivalent:

Your signing name says it all. Until you know what you want, you
won’t be able to hold a reasonable conversation on the subject of
creating some form of friendship other than dinner and movie biddies.
There’s not point stumbling through a discussion when you aren’t clear
in your own head or heart what you really do want. You seem pretty
clear about what you do not want with her, but that’s not enough to
engage another person in a serious, or even casual, relationship.
If you know you do not want to have a serious relationship, and that
you are not in love with this woman, you should have the courage to
tell her. It’s not an easy thing to say or hear, but honesty beats
exploitation every week of the year. If you do want to have a friends
with benefits relationship, you can say that. But beware the human
heart, not to mention the biology of endorphins and hormones, which
conspire to impact our emotions. It’s the rare person who can be
intimate without becoming more emotionally engaged with their lover.
One of you might be that person, but both being so is highly unlikely. I
see another break-up in your future if this goes sideways. It’s your call
if you want to risk it. Waiting and dating a while seems like a good first
step.

Leave Me Alone

Dear Jewish Fairy Godmother:

I’m single. I’m happy being single. Everyone I know is married and
thinks I should be too. They keep trying to fix me up on dates, inviting
me to dinner parties, tell me success stories about people who married
later in life and died happily ever, reunited with their lost true loves
from high school, etc etc etc etc etc ad nauseum. I did not have a true
love in high school that I have longed for over the years. Instead, I
supported two deadbeats for the better part of thirty years in two
marriages, thankfully both over, though at great cost. I’ve lived
happily alone for the past ten and travelled, gone on vacations, and
generally had a much happier and more fulfilling life. What my friends
do not know is that I have also been in a mutually consenting friends-
with-benefits relationship with a man whose wife is institutionalized
with Alzheimer’s. Because of our social standing we decided it was
nobody’s business but our own. When people say, with sincerity,
“You’d be sooo much happier with companionship….” and then wink at
me, I want to tell them, but I’ve been quiet. Other than saying “I love
my life,” what can I do?

Leave Me Alone

 
Dear Leave Me Alone:

You’re on the right track with re-inventing your life after two bad
marriages. Many women would crawl into bed and pull the covers over
their head and never go out again. The fact that you are both socially
and sexually active, and seem happy and content is a statement about
your good emotional health and ability to make good choices. That it’s
also good for your wallet is just an added bonus.

 
Tell your friends that you have taken a complete inventory of our life,
from fiscal to sexual. Say that you’re happy with every aspect of your
life, except perhaps needing to lose ten pounds, getting someone to do
your weeding, or finding a better brand of toothpaste. You can change
either of those latter two, but make them playful and distracting. Don’t
put the emphasis on sex, but if they come back with a quizzical inquiry
about you being sexually happy, say that while you’re not a prude you
don’t want to compare bedroom notes with anyone. Try to say that
with a straight face. You might practice this little speech in the
morrow, perhaps after a glass or two of wine. But no matter what,
keep smiling like the Mona Lisa. If they guess at why, you can still
keep mum about whom. And if life changes down the line, they can
dance at your next wedding or just be happy for you.

Once Bitten

Dear Jewish Fairy Godmother:

I dated someone for six months last year. It ended with a whimper
after I had surgery, and my desire for intimacy went to zero. He was a
good friend during my recovery process, but made it very clear that he
no longer considered us to be dating after the second month when I
didn’t want to cuddle or kiss. He very quickly got involved with a
woman that his ex-wife introduced him to (and apparently liked a lot
more for than she did me, as she always seemed quite hostile when
we were dating). But when I bumped into him at the market two days
ago, the first thing he said after “Hello!” Was, “I’m single again. Do
you want to get dinner and a movie on Saturday?” I accepted, but I’m
not sure if I should have added, “But only as a friend, nothing more.”
In fact I think he’s a nice enough guy to spend an evening with, but
he’s proven to me that he cares more about having a girlfriend than
being a good partner.

Once Bitten

 
Dear Once Bitten:

Having dinner and seeing a movie does not a relationship reunion
make. If he’s been a decent friend, then treat him as one, and assume
that his interest is that of a single person looking for companionship,
not automatically a hookup. If he asks you explicitly if you have ever
or would ever reconsider rekindling your relationship, you can answer
truthfully. But in the absence of that question, you should assume that
his news about being single is just that, news, not an invitation to get
back together.

 
If he does ask, and you do decline, he may ask why not. Then you can
choose to be diplomatic or brutally honest. If you value the friendship,
I’d counsel some form of discretion, and an answer that lands
somewhere near I think we are better as friends. Truth is he may
vanish again once he meets the next willing gal.

Too Picky?

Dear Jewish Fairy Godmother:

Is there ever a good way to break up with someone? We’ve been
dating for six months and there is absolutely nothing wrong with this
guy. He’s funny, smart, kind, considerate, financially independent, and
good in bed. On paper, he is exactly what I have said I am looking for
in a new partner, and certainly far ahead of the curve on either of my
previous mates or the guys I have dated between and since them.
What’s the problem? I’m bored. I know it’s not a fancy or dramatic
reason to want to end a relationship. But after six months I feel like
we’ve been together for six years, and I mean six years non-stop
locked a room and can’t breathe. The conversations are flat, the
stories repetitive, and any of “the incredible lightness of being” that I
have felt before when I fell in love with someone seems not just
elusive but remote. There’s no sense of yearning, no sense of
excitement, and the old-robe- and-slippers familiarity is stifling. If I feel
that now, what would happen in a year or four? I’m not getting any
younger and can’t afford to waste too long with the wrong guy.

Too Picky?

 
Dear Too Picky:

You left out loyal and kind from your list of descriptors. There are
hundreds of women who would race a moving train to be in your
situation. And while I am empathetic at your longing for the romantic
ideal, most lives are lived at a simpler, and yes often boring, pace.
Embrace the relationship for what it is: solid and reliable. Suggest that
you surprise one another with alternating responsibility for surprise
adventures. Enroll in a tango class. Or a cooking class. Or lean to play
an instrument or foreign language together. Commit to a volunteer
effort where you will assist those whose lives make yours look like
paradise. And if you are really ready to toss away a safe but boring
relationship, tell your honey you want to date other people. But please
don’t write me six months from now and tell me there are no good
people to date.