Ask a Bougie Chick

A WTF Ask a Bougie Chick...



Sooooo...

I got a ping on Facebook a month or so back from a woman (we'll call her Isshe - as in, Is She Kidding Me With This!) who wanted to know what I would think about my man spending time in the basement before he came up to bed every night. Wait for it...

He was spending time in the basement watching sex tapes of himself and his ex-mistress. Yep. Isshe wondered if she should read something into that... Oh, and also... Dude (we'll call him WhatTha - you can guess why) had recently "loaned" ex-mistress $10,000 of THEIR money for "reasons he didn't want to share." Isshe and WhatTha have been married for three years and he began this behavior three months ago. Isshe doesn't know what she should do or if she should even be upset. 

So many questions. One - when Isshe called naked-sex-tape-woman (NSTW) an ex-mistress, what does this designation mean? Mistress implies one who is in a relationship with a married man. Was NSTW a former extramarital of WhatTha during this marriage or was he married before? Either way, EITH-ER WAY, it is not cool (So Not Cool) for him to have and watch cocoa videos of him and the ex but especially not before coming to bed with the new. Nawl. 

Next question, 10k? 10 large? Diez mil dolares? My dollars? Even if you are ballin' like that, fund disbursement over $200 must be discussed and agreed upon before it goes out the door. ESPECIALLY to your husband's ex-whatever. Isshe, girl - woman up. You are being played so hard, we should nickname you XBox. I cannot. Surely you know the answers before you wrote in? None of this is okay. Not remotely. By zero stretches of the imagination. But hey, do you...

Then as if she didn't like the answers I had given her, I got another message a few weeks later from someone using a different name asking this:


Um...
*flings monitor off desk*
I'm out. Bougieland, what ya'll got for Isshe?

Ain't nothin' changed but the date on the calendar


One of the Ask A Bougie Chick letters I just received was from a 23 year old lady who recently ran into her ex. Dana and her former-beloved, Nick were together all through college. Upon graduation, Nick told Dana that he didn't want to be "held back" or "tied down" so he broke up with her. No long goodbye, no I'll-be-seeing-you, just out. The evening of graduation no less. She got back to the spot and all his stuff was just gone. He put a post-it note next to his key that said, "Be well." And the part that really ticked off Dana? He had changed his Facebook status before breaking up with her. (Let me take a moment to thank Jesus that I didn't have to date with social media in my 20s) Back to this... Very classy, Nick. 

Fast forward 11 months to last week. Alumni happy hour. Who strolls up to Dana all smiles as if they agreed to remain friends? Yep. Nick sits down, tells her how great she looks and wants to catch up. Nick got caught up in a layoff at the bank where he was working while pursing his MBA and is not sure how he can afford to pay for the rest of his advanced degree. Dana is in the executive training program of a well known Silicon Valley tech company and the VP loves her. (Karma is that bitch, ain't she?) Anywho, Nick says he wonders if he was too hasty last year. He wonders if there's any of the old Nick-n-Dana sparks still smoldering that can whip back up into a fire. (Okay, I got dramatic. Ya'll know I write romance.) 

Dana says she'll think about it. And walks away. Since then, he's going full court press. Sent flowers to her job, dropped off her favorite takeout to her door, left messages on the phone and sent her the digital equivalent of this generation's mixtape via iTunes. 

Dana says she never got over Nick and her question to us is... have we been through this, do we have any insight and what should she do.

Hey Dana! Yes, we've been through this. The abrupt "deuces" followed by lack of closure and then later yonder they come back 'round with Le TapBack. There are so many posts about re-visiting the "ex-files" on here that you could pick anyone of them. They all basically say, "There's generally a reason why you broke up in the first place but... Do you." However, I actually have a few other thoughts: 
1. What happened to him not wanting to be tied down or held back?
2. What's his hurry?
3. Why don't you date around? If Nick is the one, he'll be the one today, tomorrow or next month.
4. I know men don't always apologize for the shiggity they do but um... he got to do better than "Hey, what's been up, pretty lady?"
5. Lastly, double-check his motives. You're doing well. He is on some struggle. Is he looking for a girlfriend or a sponsor? I'm just asking.
Dana, the game is the game is the game. Decide whether you want to play and if so, is he the one you want to play with. Those are my abbreviated thoughts. BougieLand, whatcha got for Dana?

The Long-Awaited Follow-Up to the Henry & The House Invaders #AskABougieChick


In early March, I posted a story about Henry. A divorced man with two kids whose ex-wife had hoodwinked and bamboozled him into allowing her to move back into his ancestral home and brought along her new, younger, unemployed boo thang.

Since then, quite a few things went down. Henry called his lawyer who called a judge. All agreed that foolery happened. In the meantime, Henry sent Andrea (the ex) and Curtis (young boo) to Vegas for a weekend with a pre-paid credit card. He knew they would be there until the money ran out. Henry wised up.

While they were gone, he moved them out and moved them to (you will love this)... Curtis' mama's house. The kids admitted that they didn't want to live with their mother and Mr. Curt any more. When Mama and Curt rolled their broke behinds back from Vegas, they were greeted with changed locks and temporary court orders. Until Andrea could provide a stable environment where the children felt safe, Henry would have custody and Andrea would have supervised visitation.

Henry's lawyer also advised him to move his house and assets into a trust. And that he should tell Andrea that his assets revert to his sister in the case of his death. Whoa. Lawyer said he didn't put it past old girl to disappear Henry in hopes that all of his assets would go to the kids and she could control them as mommy dearest. Now that's some hot mess.

In better news, Henry is dating the legal secretary from his lawyer's office. He was there so often, they started eating lunch together everyday. That's one cloud with a shiny silver lining. So... all's well that ends well? Henry has one last question for us, "Anything I should do different this time around?"

Yes Henry. One, take your time and communicate. Two, if it feels wrong, it ain't right. And three, talk to your kids. They tend to have great radar about people. Good luck sir...

Any parting words for Henry?

Ask a Bougie Chick - Hoodwinked, Bamboozled and Led Astray


I know it's been forever and a day since I answered any of these and I apologize. I do. Life gets in way of well, life sometimes. But this one had me so nonplussed that I had to respond quick, fast and in a hurry. Here we go (buckle your seat belts):
Dear Ms. Chele,
I came across your blog when a buddy of mine submitted a letter about two years back and you gave him some solid advice as well as some tough love. You like to say that when people write in they already know the answer to the question and that's probably the case here but I still need some cosigning. 
I'm Henry, 46 years old, living in the Inland Empire east of Los Angeles. I was married for 15 years been divorced for about nine months. Equal fault divorce, we didn't take care of the relationship and when things got bad we let them slide. I ignored her, she ignored me. Well it was time to walk away even with two kids, a boy (9) and a girl (7) between us. The divorce wasn't too bad. To get it done, we split custody and I caved on alimony and child support but kept the house. The house has been in my family for three generations left to me in my grandparents' will, wasn't giving it up no matter what. Plus we just finished remodeling it..
Four months ago, Andrea told me she was having trouble making rent at her townhouse in Pasadena. I gave her a little extra to get her caught up. Two weeks ago, she said she was being evicted and could she and the kids come stay with me. Everybody said I should tell her that I would take the kids while she got back on her feet but I didn't want to do that to the kids. I said okay everybody could come back for six months but after that, she would have to leave the kids with me if we wasn't back on her feet. She agreed. 
Two weeks ago, they all pulled up and there were two guys with them. I thought they were movers. I gave her the keys and went to work. When I got home, one of the guys was still there. I asked what he was still doing there and he (Curtis) said he lives here now. She brought her new boyfriend to move in. He can't be 30 years old and has moved into my grandmother's house. 
I didn't want to make a scene in front of the kids so I pulled her into the kitchen and told her that he had to go. She said they are engaged and he'll go when she goes in six months. Ms. Chele, I was so mad I had to walk away. Finally I said they had a month and then the two of them had to go. I talked to my attorney and he said I shouldn't have let her back in without getting a new arrangement from the court but that I needed to do that now. My sister said I need to watch out that I don't leave for work, come home and find all the doors changed. Andrea doesn't work and doesn't look like Curtis does either. He works out all the time. Isn't that crazy? The kids don't like him and neither do I.
What would you do if you were me?
Henry 
Wooooosahhhh.... deep breath in. deep breath out.

Henry? Do you mind if I call you Hank because it's about to get personal. You have been hoodwinked, bamboozled and led astray. 

*pausing for church organ riff and for Sister Somebody to cut a step in the aisle of Bougieland waving a lace church hankie*

You say your ex-wife gets alimony and child support but ran through your money even when you gave her extra and then she politely sashayed back with the kids and her boo-thang into the house your beloved grands left you? The hell you say?!

Okay.... Let's first admit to ourselves that you got got. The ex-wifey Andrea done played you like a fiddle. But it happens. Shake it off. Let's also concede that she's probably been seeing Curtis (or someone like him) for more than a minute. She was having trouble making rent because she's flossing and she has Curtis to pay for as well. Pasadena is not cheap and I doubt Curtis is either. Lastly, let's understand that the one thing she did NOT get in the divorce was the house and she wants it. She wants ev-ery-thing. Ev-ery-thing? Ev. Ery. Thang.

You, Hank - are too nice for your own damn good. What would I do? Lemme tell you - Have your attorney file some motions. I'm not a lawyer, I don't know what kind but surely there are some that can work for you in this instance. NEXT - Find a reason to get Andrea and Curtis up out your house for a weekend (like THIS one coming up) and call some movers to pack up and drop off all dey shiggity over to the Extended Stay Spot where you can pre-pay a single room for them for a week. Not a month, not several weeks, one damn week. Hank. It's time to put a little gangsta in these here negotiations. 

It does not sound like Andrea or Curtis are disabled unless we are counting shady and shifty as a legal disability these days. Get a court order. Put them out. Change your locks. Keep your kids, your house and your money where they belong - with you. But what do I know? I'm not a relationship expert, married or shacked up with a buff 20-something. Let me turn it over the crew...

Bougieland... what say you? Please talk to Hank. I am unable...

Ask a Bougie Chick: "Don't Wanna Be a Playa..."


Today's letter comes from Dixon. Young brother out in Northern California going through a quarter-life struggle. Read and respond if you will...
Hi Mrs. Grant,
I found your blog because my ex had your book, Sweet Little Lies, on vacation with us in August. We ended up getting stranded and with nothing else to read (no offense meant), I picked up the book and read it. Really liked it. Your blog was listed in the back and I've been reading and catching up on some of your BougieTales and Bachelorette Chronicles. Some made me laugh, some made me shake my head but I liked how you kept it real. I'm writing in to see what you and the rest of Bougieland has to say about my situation. 
My girl (S) and I had been together for four years. We met after sophomore year, we both went to B-school for finance and we both graduated last May. I took a job in San Jose, she's in the City. Right after our summer vacation she sits me down and tells me that she wants to break up for a year so we can be sure we're really right for each other and it's not just like we're comfortable with other. She also said she wants me to "sleep around" and get some more experience in that area.  
I admit that dented the heart, the ego, the plans I had for the future everything. I don't want to sleep around. That's why I picked a girl I thought was great for the long haul and settled in. Like I did everything right and still I'm losing. Is she saying I need more expereince, am I seriously supposed to wait for her to do whatever for a year? Don't I deserve some sort of explanation? Anybody been through this before? Thanks for listening.
Dixon in Mountain View
Hey Dixon,
Mrs. Grant? Uh Grant is a pen name and I have no Mr. but I love the formality... Glad your enjoyed Sweet Little Lies, it's truly the gift that keep on giving. Feel free to buy the entire catalog... Moving on... 
I don't want to bruise your ego more than S already did but let me clue you in on some relationship code words: 
  • When an s/o tells you that they "want to take a break" that means they want to break up but either are a) too chicken to say it or b) too selfish to let you go completely. 
  • When an s/o says they want to see if you are really right for each other, that means they don't think you really are and last but certainly not least
  • When an s/o says they want you to sleep around? That's deflection because they already are.
(At least in my experience)
So I don't know what happened or why but S has moved onto the next but she sure has and you need to do so as well. You do deserve some sort of explanation, you may or may not get one. Don't put your life on pause waiting for it. As we've said in many posts before, you may not have done anything wrong or different. Things and people change. It's up to you if you want to check back in a year to see what's up with old girl. Chances are, she'll see the error of her ways before then and try to come back, it happens. Or in twelve months you can roll past her spot with your new boo, raise a glass of champagne up while Whitney sings "Learned from the best" blasting from your speakers. Whatever works for you. For now, keep it pushing.

BougieLand, agree or disagree? Any words of advice for Dixon? Been through it? Wrote a song about it? Do share...

Ask a Bougie Chick: Naive or Neurotic?


Today's letter comes from Kaylah. She's 22 and this is her first "serious boyfriend' ever!!! (She used the extra exclamation points.) Okay, Kaylah, I'm sorry for teasing. I know you are super-excited about the boo and just want some folks to level set your expectations. We are so here for you. BnB, it's a little wordy but bear with it...
Dear Chele (can I call you Chele? I kind a just did!!),
I'm 22, single, black and just finished my degree, a B.A. in Finance. I head off in January to start my MBA because what in the world would I do with an undergrad degree in Finance!! I don't know. Anyway, as you say, moving on...
I've been dating this guy. Isn't it always about a guy!? We've been seeing each other for close to a year. He's white which isn't really relevant, I'm just sharing. He's my first "real" like "serious" boyfriend!!! (read, first guy I've ever slept with, had serious feelings for, all that) His name is Corbin and he is awesome! He's gorgeous, smart, funny, popular, athletic. I'm kind of bookish but cute in a librarian kind of way. He's the outgoing one, I'm more introverted, I guess. Anyway, I think we match that way.
There are just have a few things that my girls have brought to my attention which I didn't think were a big deal but now I'm wondering. 
So when we first starting going out, I was a little bit overweight. Twenty-five pounds or so. He didn't seem to care and liked me for me. We didn't go out a lot just hung around my dorm room and stuff. I started working out just to feel better about me. I ended up losing about forty pounds and I like not worrying so much about my weight. I can tell from the compliments and looks that I'm looking my best. Finally got my natural hair to grow out in cute curls but you probably want me to just get to the point?! At this point we did start going out more but I don't think that's because I looked better. The weather was better and I felt more like going places. He doesn't like to talk about our relationship, we just know we're in one. And he doesn't like to flaunt our relationship so we don't hang around his friends much. My friends say that is a red flag too but I think he just likes being private.  
I'm getting to my point. Last week, I ran into one of his friends at a bar. He was kinda coming onto me and so I said, "You know I'm with Corbin, right?" He said he didn't know and was I sure Corbin felt the same way. Then he intimated that he was interested if Corbin and I weren't together. I told Corbin this and ever since then, he has definitely made a point of introducing me to his friends as his girl. Maybe it's more of a white boy thing? I asked him what he thought was next for us and he kind of turned the question back around on me. Now I'm wondering if he's in this or if I'm just convenient or what. Not sure what to think. Am I being naive or neurotic? Any advice?
-Kaylah in Florida
K (can I call you K, yep, I just did) ~ Girl. That's a lot of energy and angst you've got going there. My first bit of advice would be for you to take a deep breath. Woo and sah. Now, this is your first boyfriend. You gotta kinda feel your way around this one. And by that, I mean you need to ask direct questions and get direct answers. Questions such as "What is this and what do I mean to you? Where do you see this relationship going next?" It's not anyone's job to guess. 

I have to admit that at a quick glance, there is some crimson-flaggery wafting about. What's with his good friend not knowing he's in a relationship and more specifically, with you? How coincidental was it that he started taking you out in public the minute you got fine? If it's not relevant that Corbin (we would have guessed from Corbin) is Caucasian, why mention it... twice?  Waiting to claim you after one of his boys shows interest is not a white boy thing. It's a male thing. To him, your value is validated and enriched by his friend's attraction to you. Sucks and childish as all the damns but there it is.

I often say that people write in here when they already know the answer and just want validation. Kaylah, soemthing about the entire situ has you flustered. Step back and analyze that for a minute. What do you know and what do you think? Next, what do you want? Is this a relationship you want to take in B-school with you? And if so, why? You look good, you're about to be double-degreed, you're young, you're in Florida and more than one man has his eye on you. Just let that soak in while you decide what to do next. You decide. You. Don't wait for Corbin to tell you what he wants,you tell him what you want and he either steps up or steps to side. Go get your life, girl.

BnB, advice for K? Comments, musings, memories? Bougie brethren? Thoughts about Corbin? Do assist a young sister...

Is "once a cheater, always a cheater" a fair assessment?

Today I'm responding to a letter from Kian, a 27 year old gent from St. Louis. Let's have a look: 
Hi Michele, I'm writing in because I'm getting conflicting answers from the people I actually know and I've noticed that you and your readers tend to just speak plain. I'm dating an incredible woman, she's a little older, 32. We've been seeing each other for almost two years now. I knew she had been engaged before and it really didn't bother me. 
I just found out (not from her) that she's been engaged twice and both times the relationships failed because she was unfaithful. I'm not lacking in self-esteem and I have a healthy amount of ego. I mean to say I'm not worried about not being enough man for her or whatever that syndrome is. But as I start to consider asking her to be my wife, I'm valid in having a concern, right? 
Every situation is different but at the very least, I should discuss with her before fully committing? How much of a person's history can you really judge them for? A person with a history of infidelity doesn't necessary repeat the pattern or do they?
-Kian
Kian, that is discussion worthy at the very least. As a matter of fact, I'm a little confused that you asked others (and me) about this before speaking to her. It lets me know that you probably already had some reservations? Not a condemnation, just an observation. Yes, the fact that she cheated on her two prior fiances is troublesome and you would need to understand 1) if it's true 2) why she did it and 3) what has changed/matured about her that she wouldn't do it to you. As for how much of a person's history you can judge them on - well, none really. You can take their past into consideration but you really aren't supposed to judge them for it. Glass houses, rocks. Judge not... all of that. Realistically however, I understand giving a healthy side-eye to someone with a sketchy track record. You two have been together for two years though, any worries prior to hearing about her past two imploded relationships? Just something to think about.

BougieLand, what say you? Once a cheater, always a cheater? If they cheat with you, will they cheat on you? Would you date someone with a history of infidelity? Thoughts for Kian? Do share...

Ask an HR Chick: Getting Personal while Professional


Sometimes the Ask a Bougie Chick question wakes up my inner HR guru and I have to answer from both a bougie and an HR perspective. This letter did just that. Please read this letter from Nessa in Georgia.
Hey Chele,
I'm hoping you don't judge me too harshly. I did a stupid thing. It wasn't smart. I should just say it. I'm 33 years old and a married woman. I've been married for six years. I work for a Fortune 500 telecom company. A month ago I went on a business trip to Arizona. While there, I had a week-long affair with a co-worker from another department and office. He is not married but engaged to be. I could lie and say we fought it but the attraction was instant and we both just went for it knowing it was just a week.  
Like I started out with, it was stupid but it was also the best I ever had. Not to disparage my husband but I never knew it could be like that. Not just the sex but the instant camaraderie. I felt like I knew (I'll call him Gerald) for my whole life. But you probably don't care about all that. 
When I got back, Gerald and I started texting and talking every day. It's serious between us. My husband read the texts on my cell one night. He was mad as hell and confronted me. I told the truth. The next day he called my boss and told her what had happened. She told me to take a few weeks off and come back with my "life straight" - can she do that? Long story short, I'm probably going to leave my husband but I don't want to lose my job. What would you do if you were me? 
Thanks - Nessa P. in Smyrna.
Nessa. Girl. I don't want to judge but I have to ask - say what now? You were on a business trip and lost your mind. Then you came back and carried on to the extent that your husband found out, called you on it and told your boss? 

The guy you cheated with also works for the company and has a fiance? This sounds eerily similar to something else I heard recently. To both situations, I say - there's a lot of hot mess here and hasn't anyone ever told you not to sh!t where you eat?

I don't know if your boss can suspend you (with or without pay?), it depends on your employment policy. Was Human Resources called in? Usually, you are given the time off as an opportunity to clear up the hot mess so that your personal woes don't slop over into your professional life any more. Trust me, this is just as uncomfortable for your supervisor. 

First and foremost, you need to get your mind right. Marriage is serious, your continued employment is serious. You say what you and the fling boo have is serious. You're going to have to prioritize. You can NOT have it all. What's the fraternization policy at your office? If you and fling boo end up together will you work in the same location for the same executive? There could be conflict.

On a personal note - girl, what are you doing? You spent 5 days with Gerald and at least six years with your husband. Think about your next steps and choices before you do something (else) that you regret. As for what I would do? Besides not having the fling in the first place? Wow. Well, I'd take steps to safe guard my marriage and my job and let the rest of the stuff go. But that's just me.

BougieLand, whatcha got for Nessa?

At what point is enough really enough?


Today's letter comes from Arminta in St. Paul. She and her man Ken have broken up and gotten back together several times over the last decade. 
Hi Chele,
Hope this finds you continuing to be fabulous! I've been reading your blog for a while and I notice you've talked about one guy that you've been in and out of a relationship with for a while until you finally pulled the plug. I've been doing the same thing for a little over ten years. I'm wondering how you knew when it was time to let it go or just hang in? 
I've known Kendrick for years, we were drawn to each other from the start but there was always something off. Timing, circumstances, distance. Finally, we got together and it was awesome. We had a really good four year stretch a few years back that was amazing. We were both invested in each other and spending time until well - to be honest I don't even remember what it was that broke us up that time. Anyway, we've given it a try time and time again. We can't seem to stay away from each other. We've both taken breaks and during our time apart we've met other people. Ken was married briefly, I was engaged briefly, but ultimately we found our way back to each other. 
The thing is, I don't think we ever really fixed some of the things that broke us up before we just kind of gave into the idea of being together and gave it another try. This last go round, I am not feeling it 100%, I don't think he was really in it and we seem to just be marking time instead of moving forward. He's a great guy but I don't think I'm getting the best he has to give. I doubt I'm giving him the best I've got either. But I can't let go of everything we've been to each other and neither can he. Any advice from you and the Bougie group? Thanks, Arminta
Yeah, um. Le Ouch. You're kinda going Roberta Flack on me here - telling my story with your song. But in this case, let my life be your lesson. Get. Out. Now. Damn the love. Sorry. That's harsh but the truth of the matter is - love is NOT enough. More specifically, the dangling promise of some glittery future where your love is golden? Where love conquers all and everything else that is wrong fades to black? Shake it off. That whole push me-pull me, we love each other so deeply so why can't it work out? Run from that. 

All this love and whatnot? Where's the ring? If a man wants to be with you, he will put his all into doing so. He wants you happy. He has plans for the future, he has plans to back up the plans and he makes your happiness and those plans a priority. Won't be all the back and forth. What you two have fallen into is known as a rut. A comfortable rut because you know exactly what you're getting. Your rut is so worn and deep it's now a ditch. What ya'll share may have been great once, now it might be good but either way, you owe it to yourself (and to him) to see what else is out there. Don't dwell in ditches, dance in a field of daisies. Okay, that's uber metaphorical and alliterative to boot but I know you feel me.

Listen, I know all about this. Seems like there's no one else who will get you like he does. Who knows your story and has those shared experiences. That level of ease is seductive as hell. You laugh together, the cocoa is still working. But guess what, there may be someone out there who treats you better, who also gets you and who wants to make new memories with you and he comes history-free. You don't even know how much better life could be until you find yourself living it and all of a sudden it's like - wow! Is this what it's SUPPOSED to be like? Girl, don't get me to preaching. Verily, I say unto thee - get thee gone. One of you has to break the chains, it might as well be you.

To answer your first question? How did I know it was time to abandon ship? I found myself reading over old journals where I was saying and thinking the exact same thing way back then and now. My resolution for this year was no more wasted time. Tomorrow ain't promised and life is too short. 

BougieLand, agree or disagree? Can you talk to Arminta and let her know your thoughts. Anybody know what I'm talking about? Do share...

Know when to walk away, know when to run...


Today's Ask a Bougie Chick letter comes from Alexia:

Ok...so there's a guy...let's call him Baggage (since he has alot of it)....our families are close...our aunts have wanted us to meet for quite a while. We finally met in October of last year at a party his family had. We talked briefly and I was so nervous that I didn't ask for the digits or any kind of contact info. About 3 weeks later, I realized my error and contacted him on Facebook saying that it was great to meet him and that I hoped to talk to him soon. He replied and said it was great to meet me and said that he was sure we would speak. 

About 2 months later after no talking a family member of his reached out to me stating that Baggage needed help with a familial situation. (I'm a therapist by trade). His ex wife...was causing issues as far as his children are related...I helped blah blah blah...we started to talk and, I thought, fall in like with each other. We talked about liking each other and wanting to go out (which to this day has not happened). We REALLY connect on so many levels it was too good to be true.

Fast forward to January of this year...his mom had an emergency health crisis...and he is now taking care of her...we went from talking nearly every day to talking very sparingly (like once a week or less). My question is...should I fall back completely and discontinue contact? Should I check in every now and then to see if he's ok? Should I be empathetic and give him space? I'm stuck. Please help.

Alexia - I'm confused. I don't see the connection. I say this not because you didn't mention details but because you two still haven't gone out. It is my unwavering belief that people make time for the things that are important to them. If dude is that much into you, he would make a way to see you, be with you, talk to you. Since he has not, my advice is to fall back and let it go.

Actually in this case where's there is a lot of baggage and drama plus you've got family blended into the mix? I almost advise you to sprint post haste in the opposite direction. Let me ask the crew - BnB, what say you? Should she hang around to see what comes next or keep it moving?