The Relationship Judge: Why Won’t She Marry Me?

This Relationship Judge entry comes from a close friend of mine who happens to be a guy.  We’ve got to help him!  “Jeremy” is a kind, smart, hard working, funny and insightful man who also happens to be adorable.  Just had to give this background before you hear what he’s going through.  And once we help him, we’ve got to check back in periodically with him and make sure he’s doing okay.

The Facts:  Straight from Jeremy’s email:

 I was in a relationship with the wrong person for many years.  When I finally decided to move on from said relationship I was the happiest I had been in my life.  She was a wonderful person, just not the one for me.  After a “fallow period,” when I wasn’t looking to meet anyone, I met the most stunning woman I had ever met.  Smart, funny, gorgeous with the most out-of-this-world personality.  She had moved to NYC to pursue higher education and  I was working at an investment bank trying to figure out up from down.  From the word, “go” we spent every waking hour together.  She would come over and study while I watched TV or I would crash in her grad school single bed while she wrote papers all night.  The perfect match. I had never felt this way about someone and was head over heels for her.

I proposed to this wonderful person after 3 years of dating and she said yes.  Shortly after that I lost my job (found a new one 3 weeks later) and life started to come at us fast. We lost track of being engaged.  Fast forward 5 years, we are still engaged.  I have begged, pleaded, cried, rinsed and repeated, trying to figure out why she won’t marry me…nothing. To further complicate things, I was recently offered a very good position in NYC.  We had been talking about moving out of the city and I told her I wouldn’t take the job if it meant losing her.  The response was, “I am leaving…you should stay.”

After 8 years together. 5 years of engagement.  The rubber had met the road.  She is leaving.

The Question: Jeremy wants to know the following: (1) Was he wrong to pressure her? (2) Should he follow her in the hopes that it’s NYC that’s holding them back and (3) What if being unhappily unmarried is all he wishes for after she leaves?

The Relationship Judge Says: JEREMY! Take that job and run, my friend.  Before I can begin to answer your specific questions, let’s start with some basic facts:

First – you are a good looking, employed, smart guy who wants nothing else but to be in a committed relationship with the love of your life, get married and start a family.  I bet that if you looked around New York City (or anywhere, really), you’ll find women by the thousands who are looking for someone EXACTLY like you.  Women who want exactly the things you are anxious to give – right at this exact moment – not some day down the road.

Second – There is absolutely nothing that your fiance will come to learn about you 6 months, a year or 5 years from now that will suddenly make her realize that she’s finally ready to have a wedding and be married.  For whatever reason, she’s having difficulty fully committing yet she is not ready to set you free.  Pretty selfish, if you ask me. If she doesn’t see you as a her husband, she has no right to keep you waiting around in the hopes that it will happen.

Third – just an observation, but it does sound like at least part of your relationship has been about you sacrificing for her.  Taking a backseat to what she wants.  Now I happen to know your fiance and grew to love her like you did because she does have a wonderful personality. She IS a lovely, great person.  But even lovely, great people make big mistakes and fall into situations that they can’t even explain. It no longer seems like this person and you are on the same page about what you both currently want.  You want to get married. Have kids. Settle down.  She seems to want these things, but perhaps not at this time, perhaps not ever or perhaps not with you?? You’ve given this 8 years and you’re no closer to finding out what the story is. This is a MAJOR red flag.

Now, to address your specific questions.

(1) No, you were not wrong to pressure her. It would be one thing if you proposed to her to keep her in NYC.  This did not happen.  You proposed 5 years ago.  You have a right to know what the heck is going on.  If she’s not telling you to move with her (in fact, TELLING you to stay in NYC and take the job) – THAT IS YOUR ANSWER.  She may not want to say it. She may not even want to admit it. But she knows in her mind that she can’t move forward with you.  She may not be strong enough to tell you.  She may never be strong enough to tell you.  Her willingness to let you go is your clear answer, Jeremy.  It sucks. But it’s clear.  It’s not really that confusing.  You love someone, you don’t move away from them.  You’re engaged to someone you love? You marry that person.  End of story.

(2) No, you should not follow her.  NYC is not your problem. Wherever you go, your problems will come with you.  But let’s play devil’s advocate. Let’s say you did move there and gave up the job.  What would you do in the new city? Would she be willing to get married then? Or would she come up with more reasons why she’s not ready?  Getting married is very easy to do, by the way.  You go to the town hall and apply for a marriage license.  A wedding can happen later.  If she’s not willing to do either (and hasn’t been willing to do so for 5 years), I don’t think that moving to a new city will help.

(3) Once you make the decision to end it, it will never be as bad as you imagine. Yes, you will miss her. Being single after being with the same person for 8 years is a huge change.  You will have plenty of moments of self-doubt.  You may try to contact her in a time of weakness. She may contact you.  The sooner you put this all behind you, the sooner you will be able to heal, move on and find someone who is ready to give you everything you’ve ever wanted.  Stay busy. Keep working out. Make tons of plans with lots of different people. It’s summer – the best time to go out and meet new people – use that to your advantage.  But whatever you do, be firm about it.  You have the ability to end this heartache once and for all and start fresh.  It’s scary out there, but what’s the alternative?  This could go on for another few years and the torture will continue. Don’t let that happen.

In summary, here’s the judgment: TAKE THAT NYC JOB.  LET HER GO. HAVE CONFIDENCE IN WHO YOU ARE AND THAT THERE IS SOMEONE OUT THERE WHO WANTS EXACTLY WHAT YOU WANT.

Your Turn: Can you please tell Jeremy that he needs to move on?  That this relationship is not going to get him anywhere good? That he’s spent enough time being patient and needs to cut his losses and move on?

Wishing you all (and Jeremy) a wonderful weekend.  Until next time, please “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter (@OfficeStace).

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The Relationship Judge: When Friends Break-Up – Whose Side Do You Take?

I’m still horrified by the bombings that took place during the Boston marathon.  I had friends running in that race and more friends watching.  Thankfully they were all safe. The runners had raised thousands of dollars for charities that they hold dear.  Why on earth would anyone want to hurt these people?  It just doesn’t make sense.  The unpredictability of something so terrifying has been on my mind for the past 24+ hours.  I sit on the New York City subways convinced that a stranger’s suitcase contains explosives or that I saw the guy with the hooded sweatshirt and backpack walking around Grand Central.  I sit on the train and am worried when there is an empty brown paper bag sitting under a seat (turns out it was just a slob who didn’t want to make the effort to throw it away). Still, it’s a shame to even have to worry about this kind of stuff.

To take our minds off of yesterday’s tragedy, I’m drafting up an important Relationship Judge entry for your consideration.  Let’s take a minute to turn off CNN and stop reliving the awful moments (with a lot more brave ones mixed in too) by losing ourselves in Sara’s dilemma.

The Facts:  Sara and Joseph have been married for a little over a year and together overall for a total of 6 years.  They met in college through Joseph’s fraternity brother, Evan, who went to high school and was close friends with Sara.  Their junior year of college, Evan started dating Sara’s roommate, Jenna.  The four of them spent a ton of time together senior year of college.  They basically all lived at Sara and Jenna’s apartment and were extremely close.  After college, all of them moved to New York City.  Jenna and Sara shared an apartment with a third roommate, Joseph went to law school and Evan got an entry level job at a financial company.  Over the next several years, many nights and weekends were once again spent at Jenna and Sara’s apartment by the four best friends.

While Sara and Joseph’s relationship got stronger and more serious, Jenna and Evan’s relationship seemed to be going at a different pace.  They were very happy together, but weren’t ready to take the next step any time soon.  Sara says that she ended up moving in with and getting engaged to Joseph once he graduated from law school and found a job.  Jenna was a bridesmaid and Evan was a groomsman. The four friends regularly grabbed dinner together, went on weekend trips and were constantly in each other’s lives.  They all lived within a few blocks of each other, making it easy to make plans and meet up.  Jenna mentioned to Sara that Evan wanted to travel, go to business school and to “see the world” a bit before settling down.  Neither of them was quite sure exactly what this meant but about 2 months ago, Sara got a phone call from a very upset Jenna that Evan wanted to “take a break.”   He needed some space to figure out what his next step was – professionally, geographically and personally.  More recently, it has come out that Evan has been seeing someone for the last couple months (overlapping with their relationship for several weeks) and Jenna is furious.

Sara is confused about how to handle her recently split friends.  Evan has been her confidant and close friend since high school and he is one of her husband’s best friends.  He’s over their apartment at least 3-4 days a week either to hit the gym with Joseph, grab a beer or watch sports.  Jenna is one of Sara’s best friends and is probably the person other than Joseph that she spends the most time with.  Sara feels torn and forced to choose “a side” since Jenna is extremely angry at Evan for moving on so quickly and Evan wants nothing to do with Jenna at the moment.

The Question: How should Sara deal with her friends’ recent split?  Does she need to pick a side?  Is she hurting Jenna by continuing to be supportive of Evan and his new relationship or even to go out on dates with him and his new friend?  Sara came home from work the other day to find Evan and his new lady friend on their couch with Joseph and it made Sara feel guilty.  Should she feel guilty?

The Relationship Judge Says:  Uchhh, Sara.  Break-ups are never fun.  Luckily it’s not you that’s being dumped or doing the dumping – but being part of the collateral damage of a break-up is not a good place to be either.  You don’t need to choose sides, Sara, but you must know that by now.  How could you possibly choose between a childhood friend and a college roommate?  Not to mention that your husband is very close with one of them.  I think Jenna should understand that.  Even if your husband didn’t have a relationship with Evan, I’d still say you can be friends with both.  Perhaps set some boundaries by not having his bring his new rebounding toy (that’s what she is, most likely) to your apartment until it gets serious (it won’t).

I’d try very hard to limit whatever information you may learn about Evan from being passed on to Jenna.  She’s hurting right now and there’s no need to rub salt in the wound.  You’ll have to put in some extra effort to make separate plans and coordinate with your husband about when Evan will be coming over to your place versus when Jenna can come.  So YES, you can and SHOULD be friends with both and should NOT take sides. It won’t be easy, but you don’t have much of a choice at this point. If you don’t want to hang out with Evan’s new lady friend, don’t.

Your Turn: How should Sara juggle her two friends during the aftermath of their break up?  Should she pick a side?

Until next time, you can receive updates if you “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter(@OfficeStace).  You can also follow me on Instagram (@OfficeStace).

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The Relationship Judge – When To Say No!

It’s been a bit since the last Relationship Judge entry.  Partially it’s because submissions have been light and partially I think we’ve all been caught up in the Bachelor season until recently.  But now that spring is here (in theory), it’s time to review, judge and spew out some good advice to those in need.

Full warning here: I’m writing this completely exhausted.  My feet are throbbing from way too much activity today.  My laptop is currently sitting on a fully set dining room table – ready for a Passover seder Tuesday night.  The fridge is stuffed to the brim with food and Wally is running around like a madman from all the different smells in here.  The most exciting part of Passover prep is that we finally broke out our wedding dishes, which have been sitting in my parents’ house for the past 3 years.  SO MUCH BETTER than the chipped Ikea dishes I’ve had since law school.  What a difference it makes to have nice dishes.  I feel like a real grown up.

Need to pull myself away from rinsing off serving platters and figuring out how to stuff my apple cinnamon kugel into the fridge so I can focus on this entry.

The Facts:  Lauren has been married for 4 years and has a 3 year old son and 14 month old daughter.  She’s a full time speech pathologist. Her husband is a dentist working with his brother to establish a dental practice.  The past several years have been especially crazy with Lauren’s husband finishing his residency and starting up a business, adjusting to life with two young kids and Lauren continuing to work full time.  There have been many long days, long nights and to add to it all, their social calendar never seems to slow down.  Lauren said that she had 10 weddings coming up in the next 5 months (all close friends, all friends that attended their wedding). Most of them are out of town weddings.  She also has at least 8 baby showers in the next several months – half are for work friends that she does not believe she can decline and the other half are either for family members or close friends.  Then there’s the constant invitations of friends for dinner – mostly her single friends – who don’t seem to understand that being a mom of two kids under 3 is not a good enough excuse for declining a “girls night out” for no reason at all.

Lauren is feeling overwhelmed about everything on her plate.  She’s constantly rushing to get home to the kids, get them fed, bathed, changed etc. and by the time her husband gets home, they are both exhausted – there is absolutely no time for them to catch up or get a moment to themselves.  She has tried speaking with her husband about getting extra help with the kids, but with him trying to start a business and his loans from dental school, their means and options are limited.  The overwhelming amount of social obligations is another sore point.  She’d like to decline some of the events, but she’s not sure she can as many of these social commitments are for family or close friends.   She’s also wondering what other young moms out there do about being invited to numerous social events.

The Question: How should Lauren handle her crazy social calendar?  She wants to know if it’s OK to simply just decline certain events without getting major resentment from her friends or guilt.

The Relationship Judge Says:  Lauren, I’m tired just hearing about your daily routine.  I’m not a mom and so for that, I can only speak from the viewpoint of someone with a full time job, a husband, a long commute and a sister with 400 kids, but here are my thoughts:

Your first priority is to yourself and your immediate family (husband and kids).  With every decision you make, you should be thinking about whether that decision is in your / your immediate family’s best interest.  Let’s take the weddings / baby showers first.  Any time you have to travel for a wedding, that automatically makes it optional.  Unless it’s your sibling, sibling in-law, close cousin or best friend.  You have two young kids and that should also give you a very good excuse to cut down on the amount of weddings you are going to.  Are any of these weddings for your husband’s friends – and would he be willing to go by himself?  Weddings can be a lot of fun, but they can also be overwhelming in terms of travel, figuring out childcare, costs (shower gifts, bachelorette parties and wedding gifts are might expensive all added up) and people should understand that a full time working mom may not be able to accept every single invitation that comes her way.  Be selective – it’s OK to say NO.  Baby showers are less of a big commitment if they are in town, but sometimes you just need a Saturday or Sunday to yourself.  That’s OK too.  You don’t have to accept every single invitation that comes your way.

As for your friends that ask you for frequent “Girls Night Out” and dinner plans, perhaps try having a one on one conversation with a couple of your closer friends out of this group.  Explain how you are feeling.  Your good friends will understand.  You’d rather cuddle up with your 3 year old, baby and husband rather than spending $14 for a glass of wine at a trendy restaurant.  Who can judge you for that?  On the other hand, you deserve a night out with your friends once in a while and it’s healthy to do that!  Plus it’s important to maintain strong friendships and the ones worth keeping will be supportive of you.  Spending time with close friends should make you feel more relaxed and loved.

Aside from all the weddings, baby showers and girls nights, it’s very important for you to make time for yourself and with your husband.  Make time for the gym.  Plan date nights.  Get a baby sitter to come regularly and have a back up as well.  It also sounds like you could use some help with your kids during the week but may not have the extra funds right now to get that help.  Do you have a nanny now and if so, could you ask him / her to stay a little later after you get home from work?  Even someone who could heat up food for you or set the table or just basically give you an extra hour after you got home to get yourself together.  Most importantly, talk to your husband about how you’re feeling and try to come up with a plan that works for both of you.

Your Turn: How should Lauren handle her crazy life these days?  Social commitments?  Hoping you moms can chime in here!

Tomorrow will be the longest day of my life, so I best be turning in. Have a great week!

Until next time, you can receive updates if you “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter(@OfficeStace).  You can also follow me on Instagram (@OfficeStace).

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The Relationship Judge – Is Mr. Dreamy as Great as He Seems?

It’s been a while since we’ve had a Relationship Judge entry so I’m happy we’re getting back on track.  I thought about doing a mock entry from Tierra asking The Relationship Judge about her issues of rushing into an engagement and how to get out of it and save face and oh yeah, convince about 7 million viewers that you’re not a rude, immature and slightly crazy female.  Maybe next time.  Today, we’ve got to help Cindi from California.  Here we go…

The Facts:  Cindi is in business school and has had her eye on an “amazingly handsome and charismatic” gentleman that was in one of her night classes last semester.  She wrote a really funny description of how she used to stare at the back of his neck in class for months and never said a word to him.  She did run into him towards the end of the semester at a local bar where the class collectively decided to go to before Thanksgiving break.  After a couple drinks, she worked up the courage to just say “hello” and they did chat for a few minutes.  Cindi describes him as “dreamy” which just makes me smile because how nice to think of any other human being as “dreamy” – this probably hasn’t happened since Dylan McKay on 90210, but GOOD FOR HER!  After their little chat, another girl in the class, Jillian, approached Cindi.  Cindi describes Jillian as the “in your face, obnoxious, loud and insecure drama queen” type.  Jillian was obviously drunk and started whispering into Cindi’s ear about how sexy Cindi’s crush was, how she wanted to do “dirty, filthy things” to him, etc.   Cindi was revolted and wasn’t sure whether to take Jillian’s comments as a way to stake her claim or just drunk, obnoxious talk.

There were only about 2 weeks left before final exams and Cindi was determined to see “Henry” in a social setting again.  She decided that on the last day of class, she’d invite him to join her and some friends to celebrate the semester being over.  That last class, Cindi’s heart was pounding for the entire hour long lecture.  She was so nervous, she considered forgetting the whole plan.  When class was finally over, she actually started heading towards the door when one of her friends forced her to go back and talk to him.  Pulse beating out of her head, palms sweaty and slightly red faced, Cindi went back to where Henry was packing up his stuff and said hello.  Somehow, some way, Cindi managed to get out that Henry should join her after the semester ended as they were going out for drinks to celebrate a few days later.  To her complete surprise, Henry’s response was, “That sounds fun, but what are you doing right now?  Do you want to grab a drink?”   Cindi said she must have turned the color of an eggplant but somehow managed to indicate that Yes, SHE WOULD LIKE TO GRAB A DRINK.

The rest of the night was one big magical blur, as Cindi tells us.  They started out going to another local bar and grabbing a drink.  They played pool.  Laughed.  Shared stories about their childhood, etc.   Two hours into their “drinks,” Henry mentioned he was hungry and asked if Cindi wanted to get some dinner.  He took her to one of the most expensive restaurants in the area, held her hand and paid for everything.  After dinner, Henry invited Cindi back to his place and while Cindi was EXTREMELY interested in going, she had work the next day and it was already really late.  Despite this, 30 minutes later, they were at her place, clothes flying everywhere.  Cindi could hardly believe this was happening.  They were up all night “getting to know each other” – I’m guessing we can use our overnight fantasy suite imaginations (but not Sean fantasy suite since he’s a Born-Again Virgin).

I wish this was one of those “and they lived happily ever after” stories, but then there would be no reason for Cindi to write in to The Relationship Judge.  So here’s what happened.  Cindi and Henry hung out several more times after that first night.  It was always at night, always sort of “impromptu” and never really consistent.  The first time Cindi went over to Henry’s place, she saw an open drawer in his bedroom containing female clothing (sweatpants, sweatshirts and pajama type clothes).  She took out some of the clothes and noticed the drawer was quite full.  When she asked Henry whose clothing it was, he said they belonged to an ex girlfriend.

WELL.  Fast forward to 6 weeks from their first night together and FOUR “additional” meet-ups later.  It was the new spring semester.  Cindi was meeting up with some classmates to discuss their class project at the business school.  It’s after 9 PM and all of a sudden, Jillian walks by and she’s wearing the SAME SWEATPANTS and SWEATSHIRT that Cindi saw in Henry’s drawer.  Coincidence?  Jillian comes over to the group to say hello and smugly lets out a, “I know I shouldn’t be doing the walk of shame at school, but guess that’s what happens when you leave a guy’s place without time to put on real clothing!”

Cindi was horrified.  She wasn’t sure if Jillian knew about her and Henry or not, but either way, it was very probably that Jillian had hooked up with Henry.  To make matters worse, both of them were now in one of her classes so she has to see them regularly.  When Cindi confronted Henry to see if he had in fact slept with Jillian, his resopnse was, “Yes. She showed up on my doorstep in the middle of the night and started kissing me after I was out drinking with the boys.  It won’t happen again.  I’m sorry.”  Henry did seem sincere about regretting the hook-up with Jillian.  Cindi also points out that she never had the “exclusivity” talk  with Henry.

The Question: Should Cindi continue to “date” Henry?  Should she say something to Jillian? If not, how on earth does she tolerate seeing them both regularly in class?

The Relationship Judge Says:  HOLY COW, CINDI! My stomach literally sank during the part when Jillian came waltzing in with Henry’s ex’s sweats on.   Well, at least I picture her waltzing.  You totally busted them! What amazes me is how Henry, as wonderful and dreamy as he might be, somehow comes off as the “victim” here.  Like Jillian showing up at his door and kissing him while he’s a little drunk leaves him helpless to do anything else but succumb to her aggressive powers.  I don’t buy it.  First off, why does this guy have his ex’s sweats in a drawer in his room still?  Did they break up that morning?  In fact, did they really break up?  Or does he like to leave women’s attire in his room for his frequent visitors?  I don’t like it one bit.

Second, I picture Mr. Dreamy as a confident, smart and savvy business guy (heck, he’s in business school).  You think he couldn’t stop a loud mouth like Jillian if he wanted to even with a couple drinks in him?  Again, I don’t buy it.  How did Jillian know where Henry lives?  And she just showed up there in the middle of the night?  Perhaps she called him (and therefore had his number to begin with?).  Something doesn’t add up here and I’m afraid you may be too swept up in the fantasy of attaining Henry to realize what is actually going on.  Henry sounds like a bit of a Ladies Man.  Factually speaking he’s had at least 3 women in his bedroom in a very short period of time.  Is that the kind of person we want to be pursuing?

My advice to you is to keep these two at a distance.  Keep your interactions very cordial and polite.  Stop calling / texting / emailing Henry.  If he invites you to do something, say you’re busy.  If he wants an explanation, tell him the truth – you’re not interested in hanging out with someone who is remotely involved or interested in Jillian.  This isn’t The Bachelor!  He can’t date multiple women at the same time.  [Side note: funny that Henry’s behavior would be perfectly acceptable on the show – even encouraged.  Maybe he should be our next Bachelor??] Even if he tries to convince you otherwise, he needs to understand that he can’t have his cake and eat it too (or in Jillian’s case, she’s more like that gross icing that makes you feel sick before too long).  Don’t let him keep you in the “gray zone” – that horrible place of the occasional hook-up without any real commitment.  That’s no woman’s land.  Be confident that the real Mr. Dreamy is still out there somewhere, waiting to meet you.  And he will run in the complete opposite direction of someone like Jillian.  In fact, if he was lucky enough to get you to accept an impromptu drink invite, he’d know that you’re a person worth getting to know and date.   There would be no Jillians for him.  Stay strong on this one.

As for Jillian – I wouldn’t worry too much about her.  In fact, you should just pity her.  She’s one of those people that is never going to be happy and you don’t have time to waste brain cells on someone like that.  The good news is that they are not the only two people at your school.  Take your friends and meet other friends.  Try new things.  Go to parties and events even if you don’t feel like it.   Most importantly – stay strong even if it’s much easier to give in to the “thrill” of a whirlwind night with Henry.

Your Turn: How should Cindi handle this situation?

Have a wonderful weekend!! The Husband is heading home to go see a Washington Capitals game with his dad.  I’m off to our last therapy dog training class tomorrow and then to my parents for the weekend.  Maybe one of my parents will agree to do a video review. Stay tuned.

Until next time, you can receive updates if you “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter (@OfficeStace).  You can also follow me on Instagram (@OfficeStace).

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The Relationship Judge: To Tell or Not To Tell

It’s a brand new year of juicy relationship issues and here at The Relationship Judge, we are ready to go.  No problem is too small to be judged – keep them coming! Today’s Relationship Judge is fairly straight forward, but kind of a crazy situation.  Which is good because it’s Friday and I could use hearing about someone else’s “craziness” on a Friday.  Here we go…

The Facts:  Lesley (I’m using that name in honor of one of our favorite Bachelor contestants this season), an old friend of mine, wrote in as she’s very stressed and needs advice.   Lesley works full time as a compliance associate at a bank in New York City.  She’s very close with her brother and his girlfriend, Whitney, who is Lesley’s co-worker.  Lesley is responsible for introducing them and they have been dating for 8 months.  Recently, however, Lesley has learned that her brother (who has a wandering eye) has been pursuing someone else behind Whitney’s back.  Lesley has urged her brother to end things with Whitney (who is already designing her engagement ring at various websitse during work) but he has not indicated if and when this will happen.  Lesley is very worried that her brother won’t do anything and the relationship will get carried out indefinitely.  She’s also worried about Whitney finding out about “the other woman” and particularly, that Lesley knew about it and didn’t say anything.  Being at work could get very awkward and stressful very fast.

The Question: Should Lesley indicate to Whitney in some way that her brother is cheating on her?  Should she get involved at all?  What happens if all hell breaks loose and Lesley is still forced to work with Whitney?

The Relationship Judge Says:  YIKES!!  This is a tough one.  Do you remain loyal to your cheating brother and keep his secret or do you fess up your knowledge to a good friend?  First off, just as you should probably never date anyone from work, for the same reasons, you should also heavily discourage a close family member from getting romantically involved with a co-worker.  That’s just a recipe for disaster, particularly when things go south.   Having good, solid friendships with co-workers is essential for a number of reasons.  Co-workers can become just like family – you probably see them more than your actual family depending on your job, so treat them kindly and honorably.

As for your question, though, there’s no easy answer here, but clearly, if Whitney rightfully thinks that she is in a committed relationship with your brother, then your brother is the “wrong” one here.  I would go to him this very second and give him the option – either he ends it or you’re telling her the truth.  Normally, I’d tell you not to get involved, but Whitney is your friend and you WILL be in the middle of it to some extent and you don’t want the middle of it to be at work.  Leave all that drama outside.   Be prepared for Whitney to put some distance between the two of you for the immediate future even if you are physically working near her.  It’s not fair – you’re just the sister to the dumper, not the actual dumper.  Still – she’ll need time to heal and get over it.  Try not to share too many details of what you did or didn’t know  – that will only get you in trouble and truthfully it doesn’t matter.  The bottom line is they needed to break up and you made that happen a little sooner.

PS – Maybe you can set her up with someone else when she’s ready?? Or nominate her to go on the next Bachelor?

Your Turn: Should Lesley get involved here?  Is it her job to let Whitney know what’s happening or should she stay out of it?

Have a wonderful weekend!! We are starting a dog training class for Wally on Saturday and on Sunday we have a dog birthday party.  This is not a joke.  Someone rented out a private room for a dog’s first birthday and we got an invite to join the festivities.  I hope Wally’s missing balls can handle the excitement.

Until next time, you can receive updates if you “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter (@OfficeStace).

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The Relationship Judge: Will Compatibility Alone Make a Relationship Last?

We received a last minute Relationship Judge submission to finish off the year with.  I think a lot of people are off this week, but hopefully you have a few minutes to chime in here and help out Amy on this one.  I’m interested to hear people’s opinions. Here we go…

The Facts:  “Amy” is 45 years old and has been dating her boyfriend “Jeff,” age 55, for 2.5 years. They have both been divorced (Amy once, Jeff 3 times).  Lately, Jeff has been wanting a greater commitment – living together or becoming engaged.  Amy’s answer has been, basically, “maybe.”  She says they get along well, their personalities seem to mesh and they resolve conflicts fairly easily.  BUT, they have different tastes, different social class backgrounds, different political views and enjoy mostly different activities (there is some overlap here as they can find some things to do together, but they aren’t really either of each other’s favorite activities).  Compared to Amy’s previous relationships, she admits this one “has less passion.”  They “get along like friends and (she does) enjoy the lack of drama.”

The Question: Amy wants to know if personality compatibility is enough to keep a relationship going long term.  I want to know what you all think about whether Amy should agree to a greater sort of commitment with Jeff.

The Relationship Judge Says: Amy – thank you for writing in and being brave enough to let us weigh in on your issue.  My gut reaction to your story is that it sounds like you enjoy the companionship of Jeff but you’re not in love with him.  If you were in love with him, you wouldn’t mind the differences in your personalities – you’d see them as complementing your own preferences and lifestyle.  Now, that said, you’re wise to consider these personality and socio-economic distinctions in advance of moving in together or getting engaged so let’s really consider them.  You’ve got different interests, tastes, political views and social classes.  None of these items individually will make or break a relationship.  Particularly since you resolve conflict well.  The real deal breakers in long term commitments seem to be over things like religion, money (one of you is in great debt, has different views on how to spend money, etc.), physical or mental health issues (addiction, chronic illness, etc.), desire to have children, meddling relatives, infidelity, etc.  Absent one of these items, you should also consider whether you’re “settling” for someone who you’re comfortable with just to have someone special in your life.  Particularly around the holidays, it can be extremely lonely to be single.

In terms of divorce, it is fairly common nowadays, but a 3 time divorcee may be a bit of a red flag for you.  Any insight on why his relationships ended? Is there any evidence to suggest that your relationship is different from his previous ones?  Also, a woman in her mid-40s and a man in his mid-50s may be looking for different things from each other than you would be if you were in your 20s or 30s.  Perhaps you are just looking for simple companionship.  But even a less passionate relationship should ideally be with someone who you enjoy the same things as.  If you combine different interests with less than desireable passion, I think that’s a formula for long term disappointment.

Put it this way.  In 10 years this man will be 65 years old.  What if you found out that he had a serious health problem? Would you be willing to take care of him?  Would you stick by him if he became disabled?  Would you want him to do that for you?  I know these are morbid thoughts, but true love, at least love enough for a lifetime commitment, should stand the test of time.  And going into it, you should have every thought and wish that the commitment will be successful.  Ask yourself some simple questions:  Does this guy makes you laugh?  Does he make you feel special?  Desired?   Is he your best friend?  When something funny or sad happens is he the person you want to share it with?  Do you miss him when you haven’t seen him in a couple of days?  When he says, “I love you,” do you feel it back?  Not every relationship is a story book romance, but you need something more than friendship to keep a marriage going.

If you really do find yourself not sure about getting engaged, perhaps you could try staying at his place (or have him staying at yours) for a few weeks and see how it goes.  Nothing provides quicker clarity on a situation than seeing the day-to-day routine of a potential mate.  A wise person once told me that if she wasn’t married to her husband when they first moved in together, there is no way they’d still be together now (it’s been 11 years and they are still together).  In other words – if you find less passion in your relationship now, think about how you’ll feel when you’re doing his laundry, he’s leaving dirty dishes in the sink and you get to smell his morning breath every day :)  In loving, long term marriages – there’s plenty of that, but the love you feel for your partner should more than make up for this kind of stuff.

Either way, please keep us posted on what you decide to do.  You’re still young and have lots of life before you – don’t settle for the wrong person, even if he is a nice guy.  For every day you’re with someone who’s less than you’d want for yourself, you’re missing out on being with someone who’s all you’ve wanted.  (They should print that on a fortune cookie).

Your Turn: Should Amy stick with Jeff?  Is there anything she could do to figure out whether he’s the guy for her? Can compatibility ever win out over passionate love?

I hope you all have a great weekend filled with lots of family and friends.

Until next time, you can receive updates if you “Like” my Facebook page (http://www.facebook.com/OfficeStace) or “Follow” me on Twitter (@OfficeStace).

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