It wasn't all that hard for Angie to find out more about May Parker, including where she worked. With that bit of information she started formulating a plan. What was a bit harder was finding out if and when May ever left the office during the day. That took a bit of her acting skill and a few tricks she'd picked up from being married to Peggy Carter for several decades. Once she was able to gather the information all Angie had to do was call Natasha and ask her out to lunch. The restaurant Angie picked was just down the street from May's office building, and just so happened to have the Thursday special that May treated herself too on the one day of the week she bought lunch instead of bringing it from home. If Natasha hadn't been able to make it on a Thursday, Angie's back up plan was to ambush May in the park. Apparently on nice days she had her brought from home packed lunch in the park. The receptionist at May's office was really chatty when the office was slow.

They hadn't been sitting at their table on the sidewalk patio in the front of the restaurant very long when Angie dared a quick smirk before shifting her expression as she seemingly just happened to glance over the top of her menu in time to see who was walking their way. "Angel, isn't that your friend?"

Natasha looked up and over her shoulder and an instant smile bloomed on her lips. That smile only grew brighter when May smiled back and waved. "Hey May."

"Hiya Nat." May greeted as she walked up to the black iron fence separating the patio from the busy sidewalk. "Hello Mrs. Carter. It's good to see you again."

"Hello dear." Angie greeted brightly. "What a wonderful surprise running into you here."

May smiled. "I work nearby, I was just heading here in fact, for lunch."

"Well in that case you just gotta join us, hon." Angie beamed at the younger woman.

May was quick to protest with a shake of her head and a hand held up. "Thank you Mrs. Carter, but I don't want to intrude."

"My little Christmas angel has promised me the whole day together." Angie beamed. She was generally thrilled to be spending the day out with her little girl. It had been awhile since they'd gotten the chance to just hang out and enjoy each others' company. "I'm sure she wouldn't mind sharing for an hour or so. Would you, angel?"

"No, of course not." Natasha replied, still smiling at May but giving her mother a bit of side eye. Something in Natasha's gut was telling her something was up, she just couldn't put her finger on it yet. "If you have the time to stick around May, please, join us."

"Well, if you're sure." May replies, returning Natasha's smile.

It was taking all of Angie's acting skill to keep from wiggling excitedly in her seat as they waited for May to enter the restaurant and make her way to their table. As soon as May was seated, she and Natasha easily began a conversation when May asked if she was crashing a Mama and Nat date, or if Peggy would be joining them as well. Natasha explained that two days a week her Mum volunteered at the V.A. working with vets. Peggy might have taken an early retirement, but she still kept herself busy, active, and in service. Angie asked about Peter, and May gladly talked about how he was doing. Even teasing Natasha that the next time she got Peter hyped up on sugar she could stick around and deal with his hyperactivity and the pending cranky crash.

When May asked what their plans were for the rest of the afternoon Angie finally had the opening she was looking for. "Shopping. I'm treating Nattie to a new dress for my opening night next week." She smiled warmly. "One of the shows I originated back when Nattie was a baby is getting a revival. I was the lead back then, but this time around I'm playing the mother role." Angie's expression lit up as if she had just had the most randomly sudden brilliant idea. "May dear, you should come to opening night! I would love it if you would come as my guest. In fact I insist. You'll be Nattie's plus one."

And there it was, there was the reason Natasha's instincts were picking up something fishy. Her mother was playing matchmaker!

"That's sweet of you Mrs. Carter but…" May began.

"Please, hon, it's just Angie." Angie cut in, and then before May could try to refuse again Angie was already making plans. She and Peggy would treat the girls to dinner before the show, and then afterwards they would join them for drinks at the after party. Angie talked so quickly and so much that May's lunch hour was over and she had to get back to work, and since she didn't have time to refuse in a polite way she agreed to go.

Once they were alone and Natasha was sure May wouldn't backtrack she crossed her arms over her chest, sat back in her chair, and glared at her mother.

"Oh, don't look at me like that." Angie huffed at the girl while reaching for her glass of iced tea.

"Like what?" Natasha grumbled. She wasn't quite pouting but it was close, if she weren't so annoyed and slightly angry, she'd be pouting.

"You've got the same look on your face that your mother gets when she's, as she says, cross with me." Angie replied.

"What the hell was that, Ma?" Natasha demanded. "You're meddling!"

"I am not!" Angie argued and waved her hand in the air dismissively. "It was just a little matchmaking."

"Matchmaking is meddling." Natasha grumbled. "May and I are just friends, Ma!"

Angie snorted. "Please, angel, friends don't look at each other like that."

"Like what?" Natasha was starting to feel really called out and she didn't like it.

"Like you really want to know what she looks like under the long skirt and puffy top." Angie replies bluntly as she slips her credit card into the bill folder.

Natasha's cheeks blushed nearly as red as her hair. "Ma!'

"That's enough of that tone, little girl." Angie warned, fixing her daughter with a look that Natasha knew meant not to push.

Natasha grumbled, glared, and pouted even as she followed her mother out of the restaurant that she now knew was picked for its proximity to May's office. "How did you even pull this off? I mean, what were the chances May was coming to the very restaurant we were for us to just happen to run into her?" Angie just grinned at her girl all innocent like and Natasha groaned and rolled her eyes as she muttered, "Yenta."

"What was that angel?" Angie asked, giving Natasha a look. She was not afraid to give her grown daughter's rear end a smack in public if she didn't keep the sass in check.

"You set me up on a date with my friend without mine or May's consent." Natasha grumbled as she kicked at a random chunk of concrete on the sidewalk as they made their way towards the corner. "What if May doesn't even know it's meant to be a date? What if she does and she doesn't really want to do it, she's just doing it because you bullied her into it?"

"It doesn't have to be a date, Nattie." Angie said gently as they walked down the street together. "And I didn't bully her into it, she could have spoken up and refused."

"You barely let her get a word in, Ma." Natasha huffed. "And dinner before the show your treat?" Natasha continued, looking at her mother with a look that said she wasn't sure if she wanted to kill her or thank her. "You don't eat before a show, Ma. You eat after. And on opening nights, Mum brings you something to nibble on and whatever new charm she's gotten for your bracelet."

Angie's first opening night on stage Peggy had shown up at the shabby little off Broadway theater with a couple of chicken salad sandwiches from the automat, herbal tea with lemon and honey, and a beautiful gold charm bracelet with a single charm, a little diamond encrusted star. Every opening night since then Peggy had come to the theater with something light to eat, tea for Angie's voice, and a new charm for her bracelet. Angie smiled fondly, a look of pure and unwavering love in her blue-green eyes for her English.

Then Angie turned to her daughter with a straight face and said, "Really Natasha you're being overly dramatic about this. I swear I have no idea where you get your drama queen tendicanies."

Natasha stopped dead in her tracks and just stared at her mother before finally shaking her head, throwing her hands up in the air, and saying, "I'm putting you in whatever Brooklyn's equivalent of Shady Pines is."

Angie laughed as she linked arms with her daughter and tugged her gently back into a forward walking momentum. "I'll just burn it down with a hot plate and come live with you and May and Peter." She looked absolutely delighted with herself. "Where is your mother if you're putting me in a home?"

"A really nice condo in Boca because she doesn't meddle in my life." Natasha answered with a smirk as she laid her hand on her mother's hand which rested on her arm.

"She meddles, she just doesn't do it so openly." Angie laughs. They walked for a bit longer since it was so nice out and then hailed a cab to Bloomingdale's. While they're in the back of the cab Angie asks, "How long has it been since you were in a serious relationship, Nattie?"

Natasha sighed. She should have figured her mother wouldn't drop this. "I don't don't, Ma. D.J. I guess."

Angie frowned. "Sweetheart, D.J. was years ago."

"I know." Natasha turned to look out the window and watch the world go by. "If I couldn't make it work with someone in a similar field of work to my own, then what chance do I have at making it work with a civilian?" She shook her head and turned to look at her mother. "I can't ask May to put up with me and my job."

"I'll be straight with you angel," Angie began, rolling her eyes when Natasha snorted at the word straight. "Lovin' your mother was always easy for me, but livin' with what she did for a livin' wasn't. I couldn't even begin to count how many nights I couldn't sleep because I was worried or scared to death wonderin' where she was, what she was doin', and if she were safe. There would be times when she was gone for days, weeks, even months sometimes, and I'd swear to myself I was done, I wasn't goin' to keep waitin' and worryin'; pacin' the floors every night waitin' on the phone to ring to hear her voice tell me she's ok, or hear someone else's tell me she ain't comin' home this time." Angie's voice cracked a bit. She felt her daughter take her hand and squeeze. "There were times when Peg and I fought about it, and a couple of times those fights got pretty ugly." Angie had to take a moment, to let the memories come and go before she could continue. There was still a bit of sting whenever she'd think about the early days, the days when Peggy was still in the field, and they were trying to navigate their relationship between missions and battlefronts.

Slipping her hand from Natasha's, Angie reached over and put it on her daughter's knee and looked into her eyes when she was finally able to continue. "But we always managed to settle things between us, we always came out of it stronger and still together, because we loved each other. There has never been a single second in my life with her, that I have ever regretted lovin' Peggy Carter. There has never been a prayer said where I haven't thanked God for leadin' her into my automat, and into my life. I thank him every chance I get for her, and you, and our life together." She smiled as she raised her hand to cup her daughter's cheek. "That's what I want for you Nattie, and my gut's tellin' me that May's your chance to have it."

"How does your gut know that?" Natasha asked, her voice soft as she took in everything her mother had said. She was and always would be in awe of the love between her mothers, and she would love nothing more than to have a fraction of that with someone. She just honestly didn't know how that could be done.

"Because you look at May the way your Mum used to look at me every time she walked into the L&L." Angie beamed as she recalled the look. "That look that says seeing her brings you joy because you're starting to have feelings for her, and then a few seconds later it shifts into a look that says, shit I'm starting to have feelings for her when I really shouldn't. You're Mum, she fought against the way she felt for a long time too, angel, but even the almighty Peggy Carter finally realized she needed to allow herself to be happy and to have a life outside of her mission."

"May has a kid, Ma." Natasha says softly. "I wouldn't just be asking her to live with what I do."

"And what were you?" Angie snorted. "A house plant? Stop making excuses, Natasha. Baby, you can have a life outside of what you do, you just gotta want it and be willing to work for it. And baby girl, I'm telling you, for what it's worth, I think you think deep down that May's worth working for it."

Back in May's office she sat at her desk looking a bit dazed and confused. She was replaying lunch over and over in her mind. She'd be lying to herself if she didn't admit that she found Natasha not only attractive but kind, sweet, funny, strong, brave, good hearted, and wonderful when it came to Peter. She may or may not have had a few passing thoughts about what it would be like to go out with her, and there may have been a night or two when she let herself wonder what it would be like to touch her, to be touched by her.

"May?" May's friend and co-worker said as she stood beside May's desk looking concerned. "Hey, May, you ok?"

May blinked. Turning her head to look up she said, "Hmm, what? Oh, Carmen, yes, yeah, I'm fine. Did you need something?"

"You looked like you were a million miles away." Carmen replied, shaking her head to answer the question about needing something. "You sure you're ok?"

"I'm fine, really." May laughed as she sat back in her hair. She bit her lip for a moment and then sat up again and said in a soft voice so no one would overhear. "I think my friend's mother just set us up on a date."

"May! That's great!" Carmen cheered. "About damn time, woman. Glad someone decided to be proactive in your love life, because you'd die an old maid if left to do it on your own."

May rolled her eyes. "I've dated, and it's not like I've been celibate since Ben died."

"Yeah, but no one's ever made you look like that before." Carmen replied. "At least not from what I've seen."

"How do I look?" May asked, furrowing her brow. She and Carmen had started at the company together years ago and became good friends. They'd even started talking about starting up a non-profit of their own someday. Carmen had been there for May when Ben died, and as she navigated her new life as a single parent. She'd also been the one May had tested the hole coming out to thing on, and Carmen's responce had been to take May to a lesbian bar and even tried to play wingwoman for her. If May had a funny look about her, then Carmen would have been the one to notice.

Carmen smiled. "Happy, excited, scared to fucking death. Ya know, like maybe this could be something real, something good, something you want, and all of that terrifies you."

Something she wants. It had been a long time since May had gone after something she really truly wanted for herself. Biting her lip again, she thought about it and smiled. "I'm going to need a new dress. What do you wear to an opening night on Broadway?"

Carmen whisled, impressed. "We'll go shopping this weekend."

Peggy is sitting in her chair, her legs curled up under her, her reading glasses perched on her nose, and a new novel in her hands when she hears the front door open and close. "Love, are you home?"

"Yeah English it's us." Angie's bright voice calls out in reply.

"Us?" Peggy repeats as she looked up from her book and out towards the doorway of the living room. She waits the few moments it takes for Angie, and to her delight Natasha, to appear, and smiles happily. "Hello poppet."

Natasha smiles at her mother as she walks over and kisses Peggy's cheek. "Hiya Mum."

"Did you two have a nice day together?" Peggy asks, as she watches her wife flop onto the sofa while Natasha leans against her chair and crosses her arms. Natasha speaks in Russian and Peggy snorts a laugh.

"What did you just say about me?" Angie demands of her child before looking at her wife and asking, "What did she just say about me?"

"Angie love, what have you done?" Peggy asked her wife as she laughs while shifting in her chair so Natasha can perch on the arm.

"Nothing." Angie huffed, crossing her arms over her chest and leaning back into the sofa as she put her stocking feet up on the coffee table. "I just took a little initiative is all."

"She set me up on a date with May." Natasha ratted her out. At the surprised look on Peggy's face she asked, "You didn't know what she was up too?"

Peggy shook her head. "Of course not darling, I would have discouraged her otherwise."

"You didn't help her dig so far into May's business she knew what day and time May had lunch at this one particular restaurant on this one particular day?" Natasha asked her mother the master spy. She found it a little hard to believe that Peggy hadn't helped.

"It wasn't all that hard." Angie said dismissively and then quickly changed the subject before her wife could scold her for meddling in their daughter's love life. "Nattie hasn't had a serious relationship since she dated your ex's son. She needed a little push, so I pushed, I'm her Ma, it's my job."

"First off, Daniel and I were never ex's." Peggy replies. She rested her arm on Natasha' thigh and was absentmindedly rubbing her thumb over her daughter's knee in a soothing manner. "We were colleagues, and at one point, even friends until…"

"He decided to be a jerk about you not being able to return his feelings because you were in love with someone else, who just so happened to be another woman." Angie's voice took on a bit of an edge, still not over how Peggy had been treated.

"Water under the bridge, my love." Peggy said gently, giving her wife a smile that showed appreciation for still feeling the need to defend her honor. "Secondly," She turned her focus to Natasha, looking up at her daughter. "What about Matthew? That wasn't serious?"

"Murdock?" Natasha shook her head and snorted softly. "No, Matt and I were just killing time together, scratching an itch for one another. He's too hung up on the one that got away and he can never really have to do serious with anyone else. He'll try, lord knows he'll try, but it never works out."

"It will work out with May." Angie says with confidence.

"Ease up a little bit, darling." Peggy advises her wife. "You've set the ball rolling, now allow them to figure things out from here."

The first step to figuring things out was to determine whether this was actually a date. Once back in her apartment after having dinner with her parents Natasha must have picked up her phone fifty times with the intention of texting May. She tried over and over to compose a message, but had no idea what to say. Leaning back into her sofa she let her head fall back. When she turned it to the side she found herself nose to nose with Goose. "Don't suppose you have any ideas? Cause I'm actually thinking of asking Tony for advice." Goose meowed at her and she sighed. "Yeah, my family's meddled enough. I'm a big girl, I can do this myself."

Snatching up her phone Natasha texted, 'I feel like I should apologize for my meddling mother. She set us up to run into you.' She sent it, then set her phone down, and then went to the kitchen to grab a beer. She could hear the alert of a new message as she returned and made herself count to ninety before picking it up to check it.

'You don't have to apologize. I've got one too ya know. First time I brought Ben home my Ma told him my ring size.' May texted back.

Natasha snorted. 'I swear I can normally ask a girl out without my mama's help.'

'And I can tell a matchmaker to stuff it when I want to.' May replied.

'So, we both actually want this to be a date?' It took a few minutes for Natasha to hit send after tapping out her response.

May's reply was simple. 'Yes.'

Natasha had the biggest smile on her lips as her heart sped up and she let out a little whoop that made Goose jump off the back of the sofa and head into the bedroom. They spent about ten minutes deciding where to have dinner, though it was mostly May trying to convince Natasha not to punish her mother by picking an overly expensive restaurant. 'Hey May?'

'Yeah?' May replied.

'I'll make you cannoli if you tell my Ma to stuff it.' Natasha sent it with a wicked grin.

'Not a chance you brat!' In her apartment several floors up May was laughing. 'Didn't I just explain that I know how Italian mothers work? I ain't stupid!'

Natasha laughed.

The day of Angie's opening night Natasha left work early so she could get her hair and nails done. Natasha's hair was shoulder length these days and she had decided to put some curls into it, something similar to how her mothers used to wear their hair, but she didn't want to put the work into doing it herself so she went to a salon instead. Then she headed back to her apartment to get dressed and do her make-up. The dress she'd gotten while shopping with her Ma was a rich green that Angie had said brought out more of the green in Natasha's eyes. Doubling down on making her eyes pop because May had mentioned once that she loved the intriguing coloring of Natasha's eyes, she'd spent maybe a little too much time getting the perfect smokey eye with her green eyeshadows. The dress went to just below Natasha's knee and clung to just the right places to show off her curves. May was two inches taller than Natasha, so she was careful about picking out her heels, wanting to be at least close in height.

Several floors up May was slipping into a light gray halter dress that cinched at her waist before flowing over her hips and down her legs to her calves. She was nervous, more nervous than she had been over a date in a very long time. Which made it harder to do her make-up with a steady hand. She was also a little on edge because she hadn't told Peter she was going on a date, let alone a date with Natasha. He adored Natasha, but wasn't hot about the idea of her dating. He was young and struggled with the idea of her with anyone but Ben, and yet he wanted her to be happy and not alone. So until May was sure where this thing sparking between her and Natasha was going, May wasn't going to mention it to her nephew. He was spending the night at Ned's, so he wouldn't even need to know she was out, let alone with who.

Natasha stood outside May's door with one hand pressed against her nervous stomach as the other reached out to knock. She took a deep breath as she waited on May to open the door, and then let it out slowly. When the door opened Natasha was smiling and ready to greet her date, but as soon as she laid eyes on May she found words escaping her. She let her blue-green gaze rake over the other woman and then let out a soft, "Wow."

May blushed. She bit her lip through a smile as she took the redhead in. "Wow's a good word."

"May." Natasha managed. "You look amazing."

"Thank you." May's blush deepened. "So do you. I can see so much more green in your eyes."

Natasha smiled. The pair stood there for several awkward but oddly comfortable moments before Natasha managed to think and ask, "Ready to go?"

May nods, grabs her clutch and locks the door to her apartment. They head down to a waiting town car that takes them to a restaurant with a view of Broadway. It was a little strange at first, the uneasy nervousness between them. They talked all the time, enjoyed each other's company all the time, but this was something different. Tonight could go off in so many directions, and they were both well aware of that. It could turn out that they were just better off as friends, or the sparks they'd both felt could ignite into something more, or it could ruin what was a really good friendship.

"Are you overthinking this as much as I am?" May asked as she turned to look at Natasha as the city passed by their tinted windows.

Natasha laughed softly as she nodded. "Yeah." She took a deep breath and shifted in her seat so she was angled toward May a bit more. "I don't have a lot of friends outside my work. Hell, even my cousin Sharon works for the same company. So your friendship means a lot to me."

"Yours means a lot to me too, Nat." May replies with a warm smile. "If I'm honest, and this might be a bit much for a first date, but the last person I clicked with so easily was Ben. So, this is all a bit frightening."

"If we're laying the heavy stuff out on the table up front then, I've never come close to what you must have had with Ben." Natasha admits. "But I'd like to, it's just, well, I want just a fraction of what my mothers have." Natasha said honestly. "And so far, no one's come even close to making me feel a sliver of that."

"No pressure," May teases, but her smile is warm as she reaches for Natasha's hand. "Or anything." She laughs. "You talk about them like they're an epic love story."

Natasha blushes. "I always thought they were."

When they arrive at the restaurant they are shown to a table near the floor to ceiling windows and Natasha is instantly captivated by the way the lights of the Broadway signs outside reflect like multi-colored stars in May's dark eyes. They order drinks and gaze out at the spectacle view as they talk about the shows they've seen and the ones they want to see.

"Ma started taking me to shows as soon as I was old enough to sit through to at least intermission." Natasha's smile was warm and amused. "Some of the shows she maybe should have waited on." She laughed. "Cats gave me nightmares for years."

"I never understood Cats." May admits.

Natasha laughed again. "I don't think anyone really understands Cats."

"I was always way more into ballet than theater, and Ma couldn't have been more supportive and proud, but the look on her face when I was Maureen in my high school's production of Rent, I thought she was going to explode she was so happy." Natasha tells May when she's asked if she ever thought of following in her mother's stage shoes. Natasha is sure that her mothers would have prefered if she'd followed in Angie's footsteps rather than Peggy's, but that was a conversation for later. Natasha didn't want to deal with that particular truth just yet.

Over dinner they talk about what it was like for them growing up in Brooklyn. May looks at Natasha with wide shocked eyes. "How the hell did you grow up in Brooklyn and not play stickball in the street?"

Natasha laughed, and shrugged. "We moved to D.C. when I was ten?"

They decided to walk to the theater after leaving the restaurant since it wasn't far and they still had time. They continued to talk, but didn't feel the need to fill the silence when it came. When they first started walking they walked side by side, close enough to talk but with a comfortable distance between them. At some point May's hand had made it into Natasha's, and she couldn't help but smile as they walked closer together. When they made it inside the theater, and as they were shown to their third row center seats where Peggy waited for them, Natasha's hand had found its way to the small of May's back. Natasha greeted her mother with a hug and kiss to her cheek, and it made May smile.

As they settled into their seats May leaned in close and spoke softly. "This is the first time I've been on a date with a chaperone."

Natasha laughed softly. "Does she still count as one half way through the date?"

The show was amazing and Angie got a standing ovation with her wife and daughter cheering the loudest. Afterward the cast, crew, and invited guests gathered for an opening night after party. Natasha's hand barely left May's, which her mothers noticed. Natasha couldn't tell what Angie had been more proud of, her show or her matchmaking? By the time the pair makes it back to their apartment building it's the wee hours of the morning, and May is giggling from champagne and sleepiness. They linger in the open doorway of May's apartment, saying goodnight. May steps closer, removing any personal space between them. Natasha reaches out and once again places her hand on the small of May's back, drawing her closer. May reaches up and slides her hand along Natasha's jaw to the back of her neck as she leans in. Natasha finally gets to answer the question, what would it be like to kiss May Parker?

The answer is; that it's wonderful.