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 ( or “Follow” me on Twitter (@OfficeStace).  You can also follow me on Instagram (@OfficeStace).



  1. “Always at night”…. “Impromtu”…. “not consistant”… It’s obvious what happened here. You became a “screw buddy” (there’s another name for it but I don’t think it’s appropriate for this blog. Anyway, you gave it up too soon sister. He lost respect for you and you became his toy.

  2. can you say “booty call”!

    • Hey now – let’s be supportive here – Cindi got caught up in the moment (at least the first time). Haven’t we all been there at some point? We may be older and wiser now, but these days, rounding the bases on the first date is hardly a crime. Still – based on his actions it doesn’t sound like this guy is interested in an actual relationship and if Cindi is, she should stay far away.

      • I won’t support or condemn someone’s personal decision with their own body. That’s their own decision. I’m not being unsupportive or supportive here. Just letting her know that this is what happened, because I think she was so caught up in his good looks that she didn’t realize he had put her in the category of a “screw buddy” and this is common treatment when you are put in that category.

        Late night calls… sporadic meetings… sometimes you hear from them, sometimes you don’t. Anyway, I understand how she got upset, but at the same time she did leave herself vulnerable to this kind of treatment by him. Don’t let some guy do this to you no matter what he looks like.

  3. I feel for Cindi because she longs to be loved. She really liked this guy and now she has to lick her wounds. In my opinion there are too many people who live like real life is like the movies.

    I agree whole-heartedly with Stacey’s advice to *steer clear* of that guy. Even if he has a million good qualities, he seems to be lacking in one basic one: integrity. Cindi should DROP HIM FAST!!! [BTW, When going out for a drink with someone you hardly know, be careful not to drink too much. That’s the oldest trick in the book.]

    Henry will probably try a few times to get Cindi back in bed with him, but if it doesn’t work he’ll soon be off in the pursuit of other women. If in her voice (or words) he senses she still cares for him, he’ll pursue her all the more. She should be civil but a bit cold. [Toughen up Cindi. There are better men out there]

    He must have serious commitment issues. Cindi shouldn’t be fooled into thinking her love can change him. He doesn’t want to change. She definitely needs to protect herself from further heartbreak and humiliation.

    She should follow your advice, Stacey. Go out with friends and eventually she’ll meet someone new with whom she can build a good, healthy relationship.

    In my opinion Cindi shouldn’t even give him the time of day. Why ask him about Jillian??? Cindi knows Jillian’s character. Henry and Jillian are two peas in a pod. Henry may be a smooth talker and just put one over on Cindi—like Bentley did to Ashley!!!

    This man may be very appealing but, I’m sorry to say, it is obvious he definitely isn’t interested in a serious relationship with Cindi. When men leave clothing lying around it is 1) a way of affirming their virility and 2) being abusive to the «new» partner(s). In other words, it’s sick or mean, or both.

    He has got issues, big ones. Cindi, run the opposite direction as fast as you can. There are good men out there and you’ll meet the one for you. Don’t settle for 2nd best. Next time try to spend more time getting to know the person before getting so physically involved. AND listen to your intuition!

    You DO deserve better. Let us know when you find him!

    (Great advice, 100% on the money Stace)

  4. Once again, rock solid advice. My favorite quote from this post has to be:

    “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.”

    No woman’s land indeed! What a pithy way to sum up one of those timeless relationship issues we face as women.

    • I totally agree with the “gray zone”–my favorite part of Stacey’s advice!

      The way I see it Cindi has 2 choices. #1–Talk to Henry and discuss being exclusive (if she wants to and thinks she can trust him). #2 Steer clear of him.

      I probably wouldn’t have the guts to really confront him and would probably just let it fade away and try to move on.

  5. Cindi! I am so glad you wrote in with this issue. I think the advice that you’ve received so far is most certainly useful, and I have just a few other comments to add. First off, there is nothing to be ashamed of by deciding, of your own free will, (which it sounds as though you did) to sleep with your dreamy crush the first night the two of you went out. I mean you’d been fantasizing about the guy for weeks! And suddenly there you are living out your dream! I applaud you for going for it and now you know what he has to offer both in and out of the bedroom. As you said the two of you never had a exclusivity talk, which might have been a little premature after four dates anyway (at least in my opinion). BOTH of you were in a position to keep your options open. I get tired of it always being the big bad horny guy who’s taking advantage of the poor innocent little gal – you’re obviously in business school which is no small feat, thus I’m guessing you have a lot going for you in a variety of ways and knew what you were doing when you decided to go for it with Mr. Dreamboat.

    Enter Jillian who CLEARLY wore the sweats to school to be provocative – I mean seriously? She knew word would get out fast, or that you would be there, to witness her wearing the used sweats (DOUBLE EW BTW who wears some strange girl’s sweats???). She said out loud that she was doing a walk of shame – I mean this girl is a real class act right? I have NO DOUBT in my mind that she did this on purpose to get to you.

    But yes there’s the rub – how could McDreamy stoop so low? But let’s face it none of his information adds up – the random sweats in a drawer, his middle of the night hook up….but then she shows up at 9 pm in the sweats? It all smells! And I totally agree with Stacey that he’s a supposedly smart business guy…but after he’s had a few drinks he just can’t resist his male impulses…..? L-A-M-E!!

    I agree with the consensus that this guy really does not deserve any more of your time or energy. You were able to live the fantasy – and I would look at it that way. It was a dream, you’re out of it now and movin on. I would focus my energies back on school and other friends. And by all means DO NOT say anything to Jillian. She is just hoping and waiting for you to give her the satisfaction….ignoring her will drive her completely mad and it’s you who will get the last laugh :-)

Add a New Comment