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hgfictionwriter · 3 days

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Maybe This Time - Part Three

Jessie Fleming x Reader

Summary: Jessie and you finally get some 1:1 time together (thanks Janine!). You work to build new memories together, but hurt from the past needs to be addressed.

Warnings: None. Temporary, very light angst, but mostly sweet fluff.

A/N: Part two and one. Part Four will likely be the finale.

"What do you think? Should I go for it?"

Jessie smirked as she saw the screenshot you sent her of her jersey in the Thorns' site shopping cart.

"I don't know. I thought you said that was too big a commitment."

"I did. But I was rather impressed at the last game. And we went for drinks after, I finally got to meet Janine – so you know, points for that. And if I think about it, I'm like an OG fan. But if you think I should get a different jersey..."

Jessie laughed under her breath, her smirk now a full blown smile as she read your message while she ate lunch. The conversation she'd been on the periphery of carried on as she ate another bite before typing out a reply.

"Oh yeah? Post-game drinks were a hit, huh? And you know, my stats are only getting better with each game 😉 And let's be honest, I'd be pretty offended if you got someone else's jersey. Except Sinc's. Because, you know, GOAT."

"Oh, well, say no more. You had me at 'stats' lol. Done. I'll pick it up before next game."

"Lol I figured. My plan all along – I know how much you love stats."

"You know me so well. I have to say, I'm kind of tempted to modify the jersey. Add some sort of patch or stitching, 'Yay sports!'"

Jessie laughed out loud, less discrete than before.

"Don't you dare lol. I've taught you better than that. But hey, if you ask nicely, I could actually sign it for you 😎"

"I'm sure I have an old group paper kicking around with your signature on it. I need to be able to wash this thing lol. What else can you offer though?"

Jessie swallowed her food hard, the bite getting caught temporarily in her throat with a wince. Okay, no signature – how humbling. However, there was an opening.

She stared at her phone temporarily before a loud clearing of someone's throat caught her attention. She lifted her gaze with a curious frown on her face to see Janine staring expectantly at her. Jessie instinctively tilted the phone inwards towards her body.

"I don't even have to spy to know who you're texting," the blonde said rather self-satisfied. Jessie looked around, heat building in her face already as she hoped Janine was the only one focused on her.

"Yeah?" Jessie retorted, attempting to appear as unfazed as possible. "You should be pleased. You keep pushing me to text her." She cracked a smirk. "Now that you don't think she's the devil incarnate for 'stringing me along' in university."

"Oh I don't think you need to be pushed," Janine teased with a wicked grin. "And I never said she was the devil incarnate." She lifted a hand to her chest in exaggeration. "I merely questioned things. But you're right," she relented, "she's quite lovely. And she gives you butterflies, and she makes you blush - more than usual - and you try to act all nonchalant and it's just too adorable for words."

"Uh huh," Jessie muttered with a flat look. Janine leaned in excitedly.

"And I have to say, I got the sense that she and I could riff off of each other and just tease the heck out of you, so that really sealed the deal for me."

Jessie rolled her eyes. "Oh yeah, that's exactly what I need in my life." She'd never admit that it actually excited her that her best friend and you could get along so well. If – and it was a huge 'if' - anything evolved between you two, it was key that you got along with her friends and family.

She started thinking about how well you got on with her parents and sister – you'd met before during your days at UCLA and they loved you. She also remembered how disappointed they'd seemed when she eventually told them that you two didn't speak anymore.

"Well, since you're so invested," Jessie went on, rolling her eyes facetiously once more as she opened her phone again and turned it to Janine, "what should I say?"

Janine squinted as she leaned in to read and it only took a moment for her expression to light up. Before Janine could say anything, Jessie snatched the phone back and placed it on her lap with a frown.

"I don't want to hear it," she pre-empted the girl.

"What?" Janine said innocently with a mischievous glint in her eye. "I am totally supportive of the flirtation between you two." She ignored Jessie's look of complaint and cut off her protest. "Her shutting down your autograph is pretty hilarious, by the way," she said with a marginally apologetic look. "Not smooth on your part – you know she's not impressed by your elite football skills. Don't lean on your Jessie the Footballer identity."

"I wasn't," Jessie nearly hissed, trying to keep her voice down and avoid drawing attention. "I was joking. Half joking."

"You were flirting, or at least attempting to. She left you an opening here though. So, you should ask her out."

"I'm not asking her out," Jessie pouted, her shoulders rounding as she scooched closer to the table. She huffed upon seeing the scrutinizing look her friend gave her. "We're still getting to know each other again."

"Fine. Don't define it as a date, then," Janine dismissed with a wave. She leaned in, folding her arms on the table. "Ask her to go for dinner."

"Basic," Jessie remarked as she sat up and crossed her arms in disapproval. She frowned. "Plus that's too date-like."

"Fine," Janine said curtly. "How about a hike?"

Jessie hummed and hawed, unconvinced. "Maybe someday. Doesn't seem right at this point though." Janine rolled her eyes in exasperation.

"Well, what did you two used to do back at UCLA?"

Jessie shrugged. She saw the frustration Janine was telegraphing at how unhelpful she was being and jumped in. "We went to drop-in art classes sometimes."

Janine held a hand up to the sky. "Thank you. Finally – something I can work with. Okay! Let's find a drop-in class for you two to go to then." She pulled out her phone and started browsing before shooting a look at Jessie as an aside. "Oh, and dinner's too date-llke, but an art class isn't? Okay."

Jessie grunted and pulled out her phone as well to look.

"Here," Jessie announced after a couple of minutes. "This'll work. She enjoyed painting."

Without further consultation, Jessie began to type out a message to you. She bit back a laugh at how Janine's head was bobbing around periodically trying to peek at the message from across the table.

"Don't send it yet! I want to see it," Janine pouted.

"You are not writing my messages for me," Jessie told her pointedly, but gave a heavy sigh as she turned her phone for the blonde to see. An affronted look crossed Jessie face as Janine let out a guffaw and snatched the phone out of her hand.

"No," Janine simply said with a wag of her finger before she started typing. Jessie reached out for the phone, but Janine turned her body away. Jessie clamored more, but stopped as soon as she noted some of their teammates glancing their way. She shrunk back into her seat, a hand rubbing the side of her face as she spoke in a harsh whisper. "What are you doing."

"Jeff. Relax. I would never lead you astray," Janine assured her. "And this is so very satisfying for me since I never got to help you with any of this during uni. Cause let me tell you, if I had been involved, you two definitely would've been living happily ever after."

Jessie breathed in exasperation. "Please. Give me my phone back."

"Okay, okay. Here," Janine said, all humour from her tone gone as she now offered Jessie a sincere smile. "Read it over, but I think this is good."

Jessie gave her a lingering stare as she took back her phone and let out another withering sigh before reading.

"Funny you should ask. I was thinking about how much I missed art classes together. How about I take you to one of the drop-in painting classes across town when I'm back from Houston?"

Jessie lifted her gaze to meet Janine's and she studied the blonde for a few moments before relenting with an inaudible sigh. It was better than her original "I don't know. Paint class?" reply. She hit send and released another heavy breath as she tucked the phone away once more.

"You're welcome," Janine said with a saccharine smile. Jessie gave her a fake smile in return, pulling a laugh out of the girl. "Hey, let's remember which one of us is engaged and which one of us is perpetually single."

"Ouch," Jessie said with a light laugh.

"I'm just teasing," Janine went on. "I genuinely hope this turns into something for you. Considering you've only come back into each other's lives, what, like a couple months ago? You two seem pretty solid already. And you seem happier."

Jessie wanted to give a dry retort of some kind, but Janine was right. You two talked every day now and the chemistry you had in university was still very much present. And the depth you once had in your friendship was something that was quite easily and naturally being broached again. Even if you'd both grown and changed, the cores of who you were still aligned well and fit together. Too well.

She'd more or less dismissed the spark of emotions that came up during your initial interactions as some sort of emotional muscle memory, but the feelings were proving to not be fleeting or diminishing.

If anything, her feelings for you were growing. And this time they felt different, too. Heavier, deeper in some way. She was a more realized person now, as were you, and it made the connection between you more substantial. Less juvenile.

Her phone buzzed. She opened her lock screen.

"That sounds like a lot of fun! Let's do it."

————

By the time your paint date night came around, Jessie was nearly buzzing with anticipation. It wasn’t an official date, of course, but she hadn’t seen you since that night after the game, and truthfully, it felt like it had been too long.

She was early - as usual - but as she rounded the corner to the building, she bit back a smile upon seeing you waiting. You were always early too, which she appreciated.

“Hey.” Jessie greeted as she approached. Again, she had to tamp her smile when you beamed back at her.

“Hey, good to see you,” you said as you stepped in for a hug, which Jessie reciprocated. “I love your shirt,” you continued when you stepped back.

“Oh,” Jessie said with a slight frown and a mild laugh as she looked down at herself in question. “Thanks,” she said as she gave a shrug and fought off a blush. She looked you up and down, not entirely discretely. “I like your outfit.”

You rolled your eyes affectionately and gave her a look. “You don’t need to reciprocate my compliment. But thank you.”

“I legitimately like your outfit,” Jessie retorted, her pitch rising and pulling a laugh out of you as you both walked towards the building. Jessie took a few quick steps and grabbed the door, holding it open. “After you.”

“Such service. Thank you,” you said, both teasing and appreciative. Jessie didn’t wink, but she did give a teasing lift of her eyebrows as you passed.

As the instructor gave their directions for the lesson, Jessie found herself distracted, glancing at you out of the corner of her eye. The whole lesson carried on like that, really. Jessie had to make a point to not fall behind as she’d uncharacteristically lose concentration. The worst, well, best, moments being when she'd lean over feigning critical assessment of your work when really she just wanted to be close.

By the end, she was decently satisfied with the forest landscape she’d painted. However, she felt it paled in comparison to the ocean sunset you’d crafted.

“I love your colours. And the little cabin you added is great,” you told her as you were both leaving, canvases in hand.

“Well good,” she said as she got to a clearing on the sidewalk and stopped to turn to you. “Consider it my gift to you,” she went on as she held it out to you.

“Jessie,” you said sweetly with a smile as you took it and looked it over more thoroughly. “That’s really sweet. Thank you. It’s beautiful. And bonus - I get my Jessie Fleming signature, but on a far rarer painting as opposed to a jersey,” you laughed. “And what a coincidence. I painted this for you.”

Jessie looked at you for a moment before a smile broke out across her face as she belatedly took the painting you held out.

“Thank you,” she said softly as she studied the image. She frowned in realization as she lifted her eyes to you. “Is this the same beach from our photo?”

You nodded. “It is. Nice eye.”

“Who knew you were so sentimental?” Jessie teased.

“Apparently not you,” you replied with a roll of your eyes, but gave a small laugh. “Come on. It’s been a while, but you know me better than that.”

Jessie was quiet for a moment as she took you in. She eventually nodded. “I know.”

A small lull fell over you both before you asked. “So, what now? Do you have to leave?”

“No.” Jessie spoke quickly with a shake of her head. “I don’t have anywhere to be. How about you?”

You shook your head in return. “Same. Well, it’s beautiful out tonight. Want to just go for a walk? We can drop these off at my car first,” you proposed as you held up the painting.

“Sure. Sounds great.”

After a short detour, you both began your stroll along the quiet, tree-lined street.

“Thanks for suggesting that class,” you said. “I don’t really get to paint or pursue creative hobbies as much anymore. It was nice to make a point of it. I can’t imagine you have much of an opportunity to focus on things like that anymore, hm?”

Jessie sighed quietly in contemplation and gave a shrug.

“Not extensively, no. But we do lots of team building, so sometimes we’ll do artsy things. And I can do hobbies and such in my down time, whether during the week or between seasons.”

She looked over to see you giving her a soft smile.

“What?” She asked.

“Nothing really. Just kind of crazy how everything turned out. You’ve achieved so much and your life is so impressive.”

Jessie was about to interject with a compliment for you, but you carried on.

“Are you happy with how things turned out?” You asked with a slight cock of your head.

“I-um, yeah.” Jessie stammered slightly, caught off guard by your question. “I mean, yeah it’s been incredible. More amazing than I could’ve ever pictured. And I know I’m very lucky.”

“You’re not lucky, Jess. You’ve worked exceptionally hard.”

She huffed lightly. “Yes, but luck is involved too. Lots of people work hard and still don’t get half the opportunities I’ve had.”

“I suppose,” you relented. “But you’ve made the most of those opportunities and haven’t taken them for granted.”

“That’s true. But look at you. You’ve worked so hard. And I know what you’ve been up against, but you’ve risen above and built a great life for yourself,” Jessie emphasized.

“Thank you,” you accepted with a half smile. Jessie knew the ins and outs of your family dynamics - something few people truly knew. You smiled more fully at her. “And look at us now. We both left LA and then found ourselves in the same city again and got to reconnect,” you finished with a laugh. "It sounds strange, but it really feels like in some ways like no time has passed. Not really, anyway. Like you and I were able to pick up where we left off."

You let out a quick sigh, giving a deep shrug as you did so. Your eyes remained trained on the ground as you two walked. "I mean, we talked the other week about my family and it just felt so different. Like, I've told recent friends or girlfriends my history and everything, and they listen and they 'get it', but it's not the same. That conversation with you – via text, no less – had more depth and weight than any comparable conversation with my exes or current friends. You were there. You know it – and me, I guess - inside and out. And even if I retell things, it's just not the same."

Jessie nodded, watching you. It did feel like yesterday when she was sitting next to you on your bed, sobs wracking your body after one confrontation too many with your family. Normally, Jessie was so analytical and tentative about her physical contact with you, but the second you started crying she put her arms around you without hesitation and you leaned in, resting your head on your shoulder as she held you. That was the first time, but it wasn't the last.

Looking back on it, maybe your girlfriends did have good reason to dislike her.

"I know what you mean," she told you. "It's different. I mean, it's the same with you in a lot of ways. You were there for me during some critical points – big decisions in my life and you understood who I was and who I wanted to be."

You smiled at her fondly. You looked ready to say something and Jessie waited. A moment passed and you exhaled, saying, "It really meant a lot – having you in my life and the support you gave me back then. I hope you know that."

"I know," Jessie accepted with a smile of her own. "And likewise."

Her mind drifted. She should probably just leave things be, but not speaking her mind is what held her back all those years before. She needed to share her thoughts and feelings if things were going to be different this time. She took a breath.

"You know, I was really shocked when we saw each other here." She paused briefly. "I don't know. We hadn't talked in so long. I think I'd relegated myself to assuming we'd never see each other or ever talk again. Despite how important we were to one another at some point."

Her statement seemed to give you pause, the mild surprise evident on your face. You eventually glanced down at the street as you two continued to walk.

"Yeah. That's true, I guess," you conceded, your voice soft.

Jessie studied you, unsatisfied with the response you gave. She pushed.

"I knew we wouldn't be able to stay as close as we were. That was inevitable with us living so far away from one another, but I don't think I expected contact to fall apart as quickly as it did." You didn't reply right away and she went on with an ironic laugh. "We went from talking all day every day, to a few times a week with a video call scattered in there, to the odd message every couple of weeks, then just texts on birthdays and at Christmas, to nothing at all."

She wasn't sure what she was anticipating, but she didn't expect you to turn to her with a perplexed frown.

"Yeah. It did taper off pretty quickly."

Despite the time that'd passed, Jessie still knew when you were telling half-truths. She gave a bit of an empty chuckle. "What else are you thinking?"

You returned her laugh with a mild look. "I don’t know. I'm just kind of confused, I suppose." Jessie frowned.

"About what?" She questioned. Faint alarm bells went off in her head when you stopped walking. She stilled her movements as well and you turned to one another on the sidewalk.

You took a moment to gather your thoughts. You spoke with a smile that didn't quite reach your eyes.

"I know it was me who stopped replying right away to messages – I don't deny that – but you weren't exactly giving me a lot to work with." You took a breath, dropping your shoulders before you spoke further. "Honestly? It was kind of feeling one-sided. Yeah, you replied, but a lot of your replies were brief and noncommittal. And when I asked if everything was okay you just told me you were busy. Which," you let out a slightly rueful laugh, "is absolutely fair. You were building this brand new, big life. Which is exactly what you were supposed to do. I don't begrudge you at all. I don’t know." You shrugged and averted your gaze momentarily. "I guess things just started to feel off."

Jessie exhaled quietly as she processed your reply. What you were saying wasn't false. It had been so long it was easy for Jessie to just recall the end result – that you'd stopped replying altogether. That you'd given up on her; on the connection you'd both built for years.

Standing here now though, if she was honest with herself, it was true that Jessie grew distant in her messages - purposefully so - knowing it would drive you away. What was she supposed to do? You two were never going to be together. And being friends was so incredibly hard sometimes because it was never just friendship for her. There was always this bittersweet feeling to everything and now that you were on completely different paths, there was an inevitable conclusion. Yet, she struggled to cut herself off cold. So instead, she took the coward's way out.

Jessie scratched the back of her head. "I was busy," she repeated. She contemplated doubling down, but thought better of it. "And I guess I was finding it hard. We were building two very different lives."

There was so much more she wanted to say, but she couldn't. What would be the point? Her chest panged when you gave her a sad smile.

"I know," you accepted with a sadness in your eyes. "And I really wanted that for you. I just - it was hard to not feel like a nuisance. Like some obligation. So I just stopped writing."

Jessie's frown deepened. She knew all those years ago that she had to be hurting you, but she could lie to herself about it and focus selfishly on herself. Seeing you talk about it in front of her wasn't something she'd anticipated.

"I didn't mean for that," Jessie said. "And I never stopped caring about you," she compromised.

"Yeah. I never stopped caring about you, either," you reciprocated in a subdued manner. Despite her role in everything, Jessie was still harbouring hurt from all those years prior and she felt compelled to push on. Sure, she'd pushed you away, but you'd let her. She erased you from her life little by little, day by day and you allowed it.

"Funny how quickly things change sometimes," Jessie went on. She didn't mean to scoff, but she did. "You didn't even tell me when you and [y/ex] broke up. You didn't even tell me you were having problems."

In years past, Jessie was your sounding board for all your girl troubles. She remembered it well – it was painful. Having to hear you either swoon or – more often – complain about your girlfriends. Hearing how they disappointed or frustrated you when Jessie knew she could love you better. Just thinking back to it stoked a fire in Jessie's chest again. While she had genuinely loved you and cared about your well-being, she'd vowed to never get stuck in that dynamic again.

You cracked a smirk. "It just seemed frivolous to bother you with something like that at that point."

Another pang in Jessie's chest. "Well," she kicked idly at the concrete beneath her, "I would've been there for you if you ever needed me. I hope you knew that."

You sighed and gave a hollow laugh as you pushed your hair back, causing Jessie to get momentarily distracted by the way the rays from the street light hit your face.

"I know," you said quietly before meeting her gaze. "And I hope you knew the same about me. I know you're surrounded by people who love you, but," you shrugged listlessly, "I'd be there for you, too."

Before Jessie could respond you gave her another smirk.

"Besides. Though you never said anything explicit, I know you didn't like her. And by the end I could see why, too. No point wasting any of our limited conversation talking about her."

Jessie bit back a smirk, but knew her eyes betrayed her. "Well, I guess that's poetic. Your girlfriends never liked me and I never liked them."

Despite the mounting tension in your conversation, you laughed and gave her a nod. Jessie didn't return your laugh though. She gave you a solemn look.

"You always deserved better than them. I know some of them were just fine, some of them even good, but they didn't seem earnest enough and they didn't love you enough."

You were taken aback by her sudden proclamation. You opened your mouth to speak, but couldn't find the words.

Jessie never understood how they didn't worship the ground you walked on. She practically did, even if she didn't show it. While those girls showed they cared through superficial acts like a generic bouquet of flowers, Jessie listened. In many ways. It was obvious to Jessie that they didn't really get you – not the way she did. And if they were so in tune with you, then why was it her you came to when things were hard or you were scared or even hopeful. If she'd been your girlfriend, she would've given you everything you needed and more. They clearly didn't.

You eventually gave a soft huff and offered Jessie a quiet smile.

"You've always been very observant. And very thoughtful. I get it now. There's a reason I'm single now. I don't want to settle anymore," you told her.

Jessie was quiet before giving a nod of acceptance.

"I'm glad to hear that."

You both started walking again, though neither of you spoke right away. There was still a heaviness in the air, but it felt different now; hopeful.

"I'm sorry for how things ended," you said as she glanced over at Jessie as you two strolled through the quiet street. "You've always been really important to me – regardless of whether we were in contact or not. I don't want to say that I wish things had been different, because I really don't see the point in regretting anything, but I will say I'm very grateful that we've had this chance to reconnect and rebuild." You paused. "I've really missed you. I didn't realize how much."

"I'm really sorry, too," Jessie said, a smile spreading across her face. "And I agree – we can't change the past, but I also appreciate the chance to be friends again. I've missed you, too."

She swallowed as she contemplated whether to add more. The lull that naturally formed told her to forge ahead.

"And you were never a nuisance or an obligation. I'm really sorry it came across that way."

"Awww, Jessie," you said in a teasing voice, lifting your conversation up again. You paused your steps and Jessie stopped and turned to you in question. "Come on," you beckoned as you waved her over and brought out your phone. "We need a new photo together."

Jessie didn't fight it. Instead, she smiled at you and walked over to stand next to you. You leaned into her and Jessie found her hand naturally gravitated to your waist. It rest there before Jessie could even realize it, but before she could fret, you looked back at her with a smile before facing forward again.

You took the photo and immediately opened up your messages with Jessie to send it to her. Jessie belatedly realized her hand was still on you and she pulled it back, holding her hands behind her.

"There," you announced. "Now we can start rebuilding our collection. Portland memories – not just UCLA anymore."

Jessie laughed and held up her phone, pointing the camera at you.

"No, come on," you whined immediately and she laughed further.

"Hey, this is part of the deal," she countered. You huffed, but eventually smiled for her. "Just remember. This goes both ways. I get new photos of you, too."

She found herself giving you a wink. "I'll allow it."

#jessie fleming #jessie fleming x reader #woso x reader #woso imagine #canwnt x reader #portland thorns

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