Well… guess who is still writing at a crazily insane pace? This crazy 25 year old lady, that's who! Lol. XD But, for real, to all of you who are reading this, welcome to chapter 1 of Trials and Tribulations! This story is a sequel to the Aleheather fanfic Propositions and Conniptions. So *SPOILER WARNING*! If you wish to remain unspoiled, I recommend going back and reading the first fanfic installment before going on with this one. Just wanted to give the fair warning! As expected by those of you who followed Propositions and Conniptions, this fanfic is going to focus on Alejandro and Heather finally trying to date and try being in a serious relationship with each other properly after FINALLY being honest and acknowledging their past issues with each other. However, where Aleheather goes… there is still of course drama and hijinx to follow between our favorite dastardly duo. But, in all seriousness, this fanfic will focus on ALejandro and Heather working on themselves and their relationship as well as navigating all the things that go along with a relationship (mainly families). I really wanted to expand more on Alejandro and Heather's personal lives in this fanfic as well as themselves as a couple in a serious relationship. So, I'll stop blabbering and let you all get to reading. This begins several hours after the final chapter of Propositions and Conniptions with Heather giving Alejandro a little ritual humiliation payback for tricking her into dating him from the previous fanfic. Also, I decided to start this off from Alejandro's POV so I hope I can continue to do these characters justice. Hope you all enjoy! :)

(Alejandro's POV)

I was trying to maintain my focus on the road… as difficult as it was right now for me to maintain my focus and my composure.

Slowly I glanced out of the corner of my eye for a moment as I looked at Heather and still just taking her in.

Particularly since she looked completely… stunning. Not that she never does look anything less than stunning from my perspective, but she really did look especially exquisite this evening.

She was dressed in a dark purple knee length, sleeveless dress with a pleated skirt, a pair of black strappy heels, and wearing a set of earrings and a necklace that matched the tennis bracelet I gave her… which by the way she was still wearing.

She was looking out the window, almost surveying the buildings and in a way I just still couldn't believe she was here with me.

After we had our discussion earlier and Heather laid out her terms, I couldn't care less.

Honestly I was just ecstatic that she finally told me she loved me and wanted to be with me in general. And more than anything I was intrigued to see what she had in store for us this evening.

Since one of her 'terms' was that she wanted me to take her on a couple dates on her terms to make us even, which I thought was fair enough and I'm not one to back down from a challenge… especially if she is the one issuing said challenge.

I can handle what she has to throw at me.

It's only a few dates and as much as she is one of the few people who can make my focus slip and with her past track record in mind plus from what I've already experienced… I was still feeling up to the task.

The price of being with Heather in exchange for going along with a few dates of her choosing seemed more than reasonable to me.

And who knows?

If I play my cards right and make the right plays this evening… there could be something more to come later tonight for us, perhaps? We do have the whole house to ourselves after all, so I'll stay hopeful and diligent on that score.

For now, I'll just stick to doing whatever she wishes and just enjoy her company.

Despite me probably being alone in this opinion, but I genuinely do just enjoy having her here with me after not seeing her for over a month.

Even though I will admit, I am already intrigued thus far to say the least.

She told me to 'dress formally', but so far I had no idea why? We just got into the Ottawa city limits and the first place she had me stop was a corner grocery store and she was in and out with a carton of eggs in a matter of minutes, still making me quirk up an eyebrow at her in intrigued confusion.

Then she told me to go to a particular street that just looked like mostly a block of apartment buildings thus far.

I kept my course until she just said, putting a hand on my shoulder, "Pull over for a second."

I continued to give her an intrigued look as I inquired, "Very well, but… this area is just apartments and that restaurant you said we were going to is several blocks away. Unless you fancy a walk together and to that I have no objection… but I'm definitely sure I can find closer parking."

"Oh no, this is just a stop by while we're in the neighborhood thing. It's nothing… Just pull over and follow my lead." She explained vaguely, a determined look in her eye as a slight smirk tugged at the corner of her mouth.

As confused as I was about what she was alluding to… I wasn't going to question it further. I just shrugged and complied with a nod, "As you wish."

I was able to get a spot on the street near this building she seemed zeroed in on.

We sat there for a few moments until she cleared her throat and said, pointedly, "Um, excuse me? Isn't there something you should be doing?"

I saw her glance to her door, knowing I'd catch her meaning.

I smirked and nodded as I got out of the car and walked over to her side and helped her out of the car, seeing her smirk slightly when she thought I couldn't see and causing me to grin in satisfaction as well.

Despite her being resistant with allowing me to do this with her in the past… I was quite pleasantly surprised to see her accepting my chivalry this evening.

Knowing Heather, I'm assuming she was most likely doing this to make me work a bit on this date.

But, I was more than happy to comply.

Like I've told her prior, I happen to quite like being of assistance to her in a chivalrous sense especially. Not only because I feel like it takes her guard down with me… but, I also honestly do it out of respect for her. Because I really do thoroughly respect Heather very much, I always have despite my conflicting feelings for her I've had up until now.

Not that it matters anymore now since we're together.

Then I was brought out of my thoughts when she said, putting the egg carton in my hands, "Just hold this and follow me."

Again, despite still having no idea what was going on, I just decided to not question it and just do what she wanted to humor her. Partially to keep up my end of the bargain and also because my curiosity was at an all time high.

But this is why Heather has always fascinated me.

Though I am probably one of the few people who knows Heather and what she's really like at any remote capacity, she's still a total enigma to me. She always keeps me on my toes and I never have a complete read on what she'll do next.

Heather truly does make life more interesting for me and I do respect and admire her for that on a certain level… most times.

I kept following her until we stopped in front of this pretty upscale looking apartment building.

Actually we were near the business and stock exchange district of the city. I imagine a lot of the residents in this area are probably brokers, accountants, or business types who want to live within a manageable distance from work… even with probably a fairly steep rent an area like this comes with.

I watched her eyes scanning over the building, almost like they were counting, until her line of sight settled on a particular window in the middle of the third floor.

She looked to me and snapped her fingers and then waved her hand at me, wanting me to give her the egg carton back. I complied before she took and opened it and proceeded to set it on this concrete pillar behind us.

She proceeded to take out 2 eggs before handing one to me and saying, "See that room with the blue curtains? That's our target. Hope you still have a good arm?"

Though I was confused about what was going on and also why she wanted us to egg that particular window… I was determined to do what she wanted.

And knowing Heather, she had a plan and reason for this course of action.

Besides, I'm up for a little mischief this evening, though maybe juvenile. I just smirked and said, giving her a subtle wink, "Absolutely, I do. I have superb aim as well, mi cariña."

Surprising, she hardly commented and just smirked as she looked at the window again before elaborating, "Great. Just keep throwing until I say stop."

As much as I was still in a state of intrigued confusion, I nodded to her as we both started throwing eggs. Mine landed first and seemed to have caught the attention of the resident as I heard a slight 'shriek', even from the ground level, coming from the apartment.

But, I held to just continuing to follow her instruction until she said, holding up her hand in front of my line of sight, "Stop."

We both held off as we saw someone approach the window as I heard her say to herself, "Wait for it…"

Then someone opened the window as I heard quite an angry female voice say, "WHO in the HELL is throwing shit at my!..."

Almost instantaneously, Heather proceeded to throw the egg she was holding still at the window and then I saw her strategy of 'timing' succeed since by the time the window opened and this quite attractive young woman in probably her early to mid twenties stuck out her head, the egg hit her square in the face.

She froze up as I also froze up in slight recognition once I got a clearer look at her.

Though I've never met her personally of yet, I did recognize her from a family portrait and several other pictures I saw when I stayed at the Wilson's that first night.

The black, shoulder length, and layered bob hairstyle and sharing a fairly similar physical resemblance to Heather, though not exact. Mainly that she didn't have a slight cleft in her chin and had a bit more of a rounded face like their mother.

She was one of Heather's sisters.

I didn't know which one she was or her name but there was not a doubt in my mind that my hunch on her identity was correct.

I actually don't know much about Heather's siblings other than she was the fourth born of five with Damien being her only younger sibling. However I did know she had 2 older sisters and an older brother who I have not yet met.

Heather's sister had her hands in the air as her expression looked almost mortified and on the verge of a vexed mental breakdown at the raw egg and egg shell sticking to and running down her face and hair.

"Look who's got 'egg on their face' now, huh Kelsey? That's for you bribing Damien into dumping Bruiser's litter box over my head at Thanksgiving while I was sleeping!"

'Kelsey', noted.

Slowly, it looked like Kelsey reached her hands up and attempted to wipe it off her face slightly until she looked down and narrowed her eyes, pointing to Heather and directing in anger in voice not quite the same as Heather's but definitely having similar inflections, "Seriously, HEATHER?! Ugh! I only paid him to do that because you dented my car for no reason, you sociopathic little bitch!"

I looked to see Heather roll her eyes and cross her arms as she countered through a scoff, "Whatever… Serves you right for your crap parking job next to my car in mom and dad's driveway since you parked WAY too close to me. Seriously? You live in the city and you still can't even parallel park or even just park correctly in a driveway by putting enough space between cars?"

"Oh, fuck off! What the hell are you even doing here and?!..." Kelsey started until she looked at me and her eyes went wide slightly.

Well, not exactly how I imagined this happening, but I can work with this.

I straightened up and grinned slightly as I introduced, putting my hand over my heart out of habit, "Ah, buenas noches! You must be one of Heather's sisters. Alejandro Burromuerto Ledvora, mucho gusto a conocerla."

She kept looking between the two of us until she looked and narrowed her eyes at Heather and said, "Heather, can you and your equally twisted casanova just get the hell out of here and continue your messed up little 'love game' somewhere else that isn't on my building's fucking sidewalk?!"

All of a sudden I felt Heather rip the egg I was holding out of my hand as she immediately threw it up at her sister with a beyond angry and annoyed look on her face.

On instinct, Kelsey ducked out of the way only to realize her critical error as the egg flew past her into her apartment and obviously cracked to pieces on her floor. Just based on my own assumption and the look on her sister's face also made that outcome pretty obvious.

I looked over and saw Heather smirking in satisfaction before remarking, "Hope you didn't have any plans, because I'd suggest you 'get cracking' on cleaning that up. That egg is going to take a lot of time to shampoo out of your carpet."

All I kept doing was watching on in intrigued amusement as Kelsey narrowed her eyes before grunting in annoyed rage before yelling, "Just… AGH! Just go to hell, Heather!"

"See you at Christmas!... Sucker!" Heather called back tauntingly, looking very pleased with herself.

After that, Kelsey slammed her window shut and turned away. We were in silence for several moments as I thought through that entire 'interaction'.

Well, that was quite… interesting.

I had not other time to ponder this as I looked down and just saw Heather grab my arm and continue to smirk in satisfaction as she said in a matching tone, "Okay, now we can go out to dinner."

We both just started to walk back to my car as I continued to process that entire interaction with Heather's sister as we walked back to my car, but I decided to think on it later.

Well, one thing is for sure that I must concede… Heather certainly does still keep me guessing.

2 hours later

We finished with dinner at this upscale Korean restaurant and now she was just giving me directions.

Though she was being very secretive about not giving me the exact address. Not that I'm feeling weary in the slightest, but I am still definitely intrigued. Mainly because dinner was also interesting… but never mind that.

Though I will say this was by far the most interesting date I've been on.

Mainly due to the fact that I can safely say I never egged someone's property on a date ever. But… even I found it quite amusing with Heather including me in on one of her little stints.

Eventually we rounded this corner and she had me pull over again until I looked over and saw what appeared to be a dance school/studio.

"I've managed to find a place I liked with an open ballroom. Since we've done all the more latin based ballroom dances more familiar to you earlier… you are in my court now. Hope you can waltz, foxtrot, and quickstep as well as you can salsa and Argentine tango." She started, a sly, teasing, and confident tone in her voice, as she practically sounded like she was taunting me.

But again… I was up for the challenge regardless.

I smirked and replied, just as confident, "Of course. Allow me to show you my capabilities first hand, mi ángel."

Right then I made my way out of the car and helped her out on her side, it wasn't even a second as she cleared her throat and looked at me expectantly with her arms crossed and a quirked up eyebrow.

I couldn't hold back a slight grin as I held my arm out to her.

As she linked her arm with mine, I couldn't help myself as I started, "Well, it's reassuring to see you're quite content doing this with me now."

She immediately rolled hers and scoffed as she responded, "Yeah, right? As if. It's called social cues. Us walking into a room arm in arm is a social symbol that we are together. So, don't get full of yourself just because of this."

I smirked and responded, "Oh, but you see Heather… you are asking an impossible task of me considering I have the utmost pleasure and privilege to be together and walk into a room with a woman as beautiful as you. Especially..." I slid my way out in front of her managed to pull her close as I smirked and rested my right hand on the side of her face before continuing, "... since I seemed to be lucky enough to have the most hermosa of the Wilson sisters as mi novia."

A blush came through on her face for a fraction of a second as I smoothed my thumb over her cheek, before she quickly pushed me away with a flustered look on her face.

"Ugh! Will you stop it?! Need I remind you who is calling the shots on this date?" She snapped, looking flustered as ever.

As much as I was trying to hide it, I couldn't deny how much I missed her… as well as missed seeing her reactions at my attempts to make her flustered.

Particularly, I quite enjoy making her blush as well. It almost makes me feel empowered to know I have the ability to do that to her.

But, I maintained my composure as I let her have it her way as I smiled and responded, "My apologies, Heather… I am most definitely at your service this evening. You have my word. So... shall we?"

I stepped out in front and held the door open for her to the dance studio entrance, motioning for her to go through first. She slowly relaxed and looked more satisfied as she remarked, walking confidently through the door, "That's better. And don't forget to offer me your arm again once you walk in."

I smirked and nodded as I said, "Your wish is my command, mi ángel."

We joined arms again as we proceeded to walk toward this ballroom where classical music was heard playing. I couldn't help myself as I glanced over slightly at her and smiled.

As much as I enjoy having her back and being together with her finally… everything isn't going to all go her way that easily.

Just you wait and see, Heather. Because I have some surprises up my sleeve as well… mi amor.

So… Heather using Alejandro to help her take a little revenge on her sister before actually going on their actual date just because they were in the neighborhood? Sounds like it tracks to me! As I've said, I do think it's a shame we never got to see more of the character's families in the show. So, I'm using the power of fanfiction to bring my head canons into life on how I envision Alejandro and Heather's respective families and their interactions within their family circles. In short, I hope you enjoyed the first family introduction of the fanfic with one of Heather's older sisters, Kelsey Wilson. Though I would concede that Heather would definitely be the most devious and sadistically twisted of her siblings… I don't see any of her siblings being 'entirely innocent' to any degree whatsoever either. After all Damien is a blackmailing little shit who constantly tortured Heather with pranks for the 'lols' when they were growing up. Basically, when it comes to Heather's siblings, next to Damien… Heather and Kelsey have the next biggest beef with each other. Kelsey, much like Heather, was a stuck up popular girl in her high school years. Mainly that Kelsey used to be the most popular girl in school... until Heather came into the picture after she had her 'glow up' so to speak after junior high and Heather completely dethroned her sister in her first year alone on all fronts like the iron fisted queen bee she ended up becoming. Lol. XD But like with most things, there is MUCH more to their story of their dislike of each other. And looks like Alejandro is trying to turn the tables somehow on Heather during her 'get even' dates. How you may ask? Stay tuned! ;) Anyway, thank you all so much for reading and constructive comments are always appreciated. Hope you all are staying safe and well during these times. :)

Stay classy as always!

Dexter1995