My Last First Date

To Those with Courage to Ask

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"Mr. Billings, you have an appointment with a possible new client this morning, and she's here. Samantha Johnson."

"Monica, give me five minutes to straighten up my desk--actually, is there a conference room available?"

"Would you like me to put her in 3?"

"Perfect. I'll hit the head and be right in."

When I entered the room and saw her, I thought she looked familiar.

"Hi, I'm Jack Billings."

"Samantha Johnson. Please, just call me Sammi. No 'e.'"

"Sammi, call me Jack. Have we met before? You look familiar."

"We have, although I'm surprised you remember. Abbie was my closest friend. I was at her funeral--actually, I was at your wedding as well. Other than that, you and I never crossed paths."

Her mention of Abbie filled my eyes with tears. Although it had been three years since her death, grief never leaves one entirely.

"That's why I recognized you. Sorry not to have realized you're the Sammi I heard so much about all those years."

"I suppose it's because of Abbie I'm here, but I need to come clean and let you know I'm not interested in becoming your client."

"That's fine. What can I do for you?"

"You can go to dinner with me."

"I thought Abbie told me you were married. Didn't she go to your wedding? But why wasn't I there?"

"My husband, Bill, died of a heart attack last year. If I remember right, one of your children was sick when Bill and I married, so you stayed home and sent Abbie."

"That's right! Jack Jr. had a fever, so I stayed home. You have a good memory. But I'm so sorry to hear about Bill--wait, was he a real estate attorney?"

"He was. Did you know him?"

"This is such a small world at times! Bill and I were both invited by a state legislative committee to advise them about proposed changes to the state's real estate code. I never connected him to you, and he probably didn't know about Abbie. I saw the obituary in the state bar magazine. Losing a spouse is a terrible experience, isn't it?"

She was wiping away some tears. "Nothing can prepare one for it."

I helped myself to a tissue as well.

"We can catch up on a lot of things later. Why are you asking me out--my answer to your invitation is yes, but why me? Is this your first date, since Bill passed?"

"About a month ago I realized I needed to move on. I have two young children, 13 and 10, who need a father, and I need a husband to love. How's that for a 'before a first date' discussion?"

"I know the feeling. Being a single parent takes a lot of courage and hard work. I have a 13 year-old daughter who had her first period last year. On my watch."

Sammi was laughing. "Let me guess. You had to run to the store for tampons and then stood there staring at all the choices."

"Exactly! However, six months before Abbie died, she talked with Allie and explained what was coming, so at least Allie wasn't terrified. Abbie even showed her how to use a tampon. I'm so glad I didn't have to cover that with Allie!"

Sammi was laughing so hard she was wiping away tears.

"I'm sorry. I shouldn't laugh so hard, but the images are fabulous. I guess once you handled that, nothing else rattles you."

"Helping her buy her first bra was nothing. I hope there's nothing worse lurking out there! But, Sammi, I still wonder why you are asking me out for your first date."

"You'll learn I'm very direct, maybe too direct at times. For years Abbie told me what a wonderful husband and father you were. You come highly recommended by one of my best friends ever. Neither of us can predict whether love is in our future, but a part of me hopes you will be my last first date. But, Jack, there's one question I need to ask. Does it bother you at all that I'm black?"

I paused, looking into her eyes, wondering why she would ask.

"I think the best answer I can give you would be to say that when we go to dinner, you will become, in that moment, the most beautiful woman I have ever dated. And, yes, I'm including Abbie in that history."

Sammi put her head down and started to cry. Almost sobbing. Since this was not an attorney and client meeting, I stood and sat next to her and put my arm around her. She leaned into me and sobbed on my shoulder.

"Sammi, what's wrong? Did I say something to hurt you?"

She was struggling to regain her composure. After wiping away a lot of tears, she told me something remarkable.

"My parents raised me with a clear understanding that I was to marry a black man. They said black girls who married white boys were despicable. Last month, when I started thinking about you, that came to mind. I realized I unconsciously feel those prejudices, even if I don't believe them. It's something I still need to get past. That's why I asked."

"So, it doesn't bother me you are black, but it bothers you I am white? I love it! If you don't mind me asking, surely at least one of your parents was lighter skinned, because you have a gorgeous brown complexion."

"Both are about like me. I suspect both have white men or women in their direct ancestry and there may have been some unhappy relationships mixed in there. Do you really think I'm that beautiful?"

"Sammi, you have two things that in my eyes make you the most beautiful woman I have met. Your skin color is exceptional. It puts pasty-faced people like me to shame. More importantly, you are extraordinarily beautiful, regardless of skin color.

"Now, before you get me to confess other thoughts best reserved for a more personal encounter, where are you taking me and when?"

"I'd like to take you to La Maison. Would Friday night at 7 work for you?"

"I can hardly wait. Are you picking me up?"

"Coming here and asking you out was far out of my comfort zone. Could I just be the girl now?"

"I'll pick you up at 7. Your home?"

"I'll text you the address. I can hardly wait, too. Thanks, Jack, for making this easier than I thought it would be."

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After Sammi left, Monica buzzed me to ask about setting up a client file.

"The firm will not be representing her, and there will be no billing for this meeting."

I sat in my office for several minutes, pondering everything that had happened. I thought back to one of the last serious talks Abbie and I had, just a week before her death.

"Jack, my children need a mother. Don't play the hero and worship my grave and try to raise our kids alone. As wonderful as you are, they will need a mother. Just choose carefully."

I haven't done as she hoped. Sure, I had gone out on four first dates. None of them made me want a second date. Today wasn't a date, but I felt closer to Sammi than the four women I dated once each, and I already know more about her.

I wished it wasn't Tuesday, with most of four workdays yet to go. I knew already Sammi was going to be on my mind.

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I wanted to make a good impression, so I planned to wear my finest suit. My shoes needed a good polish, so I went over to the courthouse, where there was an older man who had been shining shoes there for as long as anyone could remember.

"Jerry, how are you?"

"I'm good, Jack. Need that pair shined? Got a hot date?"

"Yes and yes, I hope."

I love watching a skilled man work. Jerry is as good as it gets with shoes. He told me once he learned his craft in the Marines. His brother is his partner in a shoe repair shop, and it's the best around as well.

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By Friday I was thoroughly aware that this date was different, at least to me. The days had dragged by, but I had not felt that way about prior dates. What was it about Sammi?

She lived about 20 minutes away, so I left just after 6:30. Her house was in a very nice neighborhood. Upper middle class all the way. It was a subdivision I had done the legal work on, so I had a good idea about the sizes of the lots and the type of construction. This was a higher-end area, only about eight years old.

With that thought I laughed at myself. Ever the real estate attorney!

I rang the doorbell. I was incredibly nervous. I'm never nervous!

Sammi opened the door, and I was speechless, something else attorneys are not known for!

"Jack, I'm so happy to see you. The week dragged by for me. Did it feel that way for you?"

"The longest week of my life. You are breathtaking in that dress."

Sammi was wearing a little black dress. Cut low enough to show a respectable and delightful amount of cleavage. Short enough for a lot of leg. Beautiful legs. I realized in that moment many women wear black stockings with a little black dress. Sammi's beautiful brown skin made that unnecessary.

"Remember earlier this week in my office when I said you would be the most beautiful woman I had ever dated? I underestimated your beauty."

"You are sweet to say that. I love a man in a suit, and you are strikingly handsome tonight. In my opinion we've checked the physical attraction boxes."

"I checked that on Tuesday. Consider it double-checked."

Sammi leaned over and kissed me on the cheek. "Yeah, that's true for me as well."

We walked out to the car, and I opened the door for her. I hold my breath these days when I do that. Some women want to get all feminist on me and insist on opening their own door. Like they feel a constant need to prove they don't need a man. Where's that attitude when they need a jar opened or a spider killed?

Sammi kissed my cheek again. "Thank you for being such a gentleman."

As we drove to the restaurant, I couldn't help glancing at her legs. Call it what it is. I'm a man, with a gorgeous woman.

"I'm flattered at the attention you're giving my legs."

"Sorry. Busted."

She leaned over and kissed my cheek again. "I think it's a great compliment. I doubt I will ever resent your lingering looks."

When we arrived, I had no worries about opening her door. Plus, I got to watch those beautiful legs get out of my car. Not to mention her cleavage. And her gorgeous skin!

I am such a hound. I was surprised at these thoughts. I hadn't reacted to any woman that way since Abbie died. Actually, since I met Abbie.

We were seated and looking at the menu.

"Jack, please order whatever you want and don't worry about the cost. Bill had a large life insurance policy so I'm a wealthy widow."

So many things on the menu looked great, but we soon ordered.

"Sammi, thanks for having the courage to ask me out. I know that wasn't easy for you."

"I was about to say, 'You have no idea,' but you do. Men have always done most of the asking. Do you still get terribly nervous?"

"For a first date, it never gets easier."

"I have a whole new level of respect."

"Sammi, were you an athlete in college? Did you go to Northwestern, like Abbie?"

"That's where we met. I played a little basketball."

A little? I think I remember Abbie telling me it was more than that."

"Alright, I played a lot off the bench as a freshman, then started at point guard for three years."

"Other sports in high school?"

"Soccer and track. I ran the 100 and 200, sometimes the 4X100. Jack, where did you go to college and law school?"

"In Massachusetts. For both."

"Harvard? I think Abbie told me that."

"Guilty."

"How did you and Abbie meet if you were off in Massachusetts?"

"My older sister, Lauren, married Abbie's older brother, Matt. Those two conspired to introduce us the Christmas of her--and your--senior year. It was also my last year of law school."

"Was it love at first sight? I think Abbie described it to me that way."

"I'm not sure about love at first sight, but by the end of two weeks, we were both thoroughly in love. We talked on the phone a lot and wrote long emails to each other. I flew home to Chicago twice to see her."

"I remember that now. She was so in love, we mocked her. Three years later I fell in love with Bill and that ended my mocking! Jack Jr. was a honeymoon baby, right?"

"Nine months and two weeks after we married."

"We only had two children because Bill didn't want more."

"We only had two for a different reason. Abbie's pregnancies were difficult. She couldn't face another."

"Would you like to have had more?"

"Yes. How about you?"

"I wanted at least two more. I loved being a wife and a mother."

Our food arrived, so we started to eat. Soon our talk continued.

"Sammi, you and I seem to have a desire to talk about serious things most people discuss later. Maybe that's because we have a better sense of what matters most to us. If we married, would you want children with me?"

"I think you nailed it. We both know what matters. I've thought about that question this week, and my answer is a firm yes. How about you?"

"Love after ten years of marriage is much different from love on one's wedding night. Having children and raising children brought Abbie and me together in a powerful way. I would want that with you."

There were tears in her eyes. Seeing her tears made my eyes fill with tears as well.

"Look at us. On our first date and making each other cry, and not in a bad way!"

That made her laugh.

"Jack, I'm learning you're an easy man to love."

"Let me share a secret with you. I've had four first dates--not counting tonight--and no second dates since Abbie died. I'm hoping you will be my first second date."

"Yes, please ask me out again. Even if you want to take me to McDonalds, I'll be thrilled to go out with you."

"I think I can come up with something better. Would you feel comfortable spending a little time at your home or mine tonight talking for a while? I'd like to find out things we would enjoy doing together. Other than you mopping the floor with me at basketball!"

"Oh, and I was so looking forward to seeing you in your short shorts, white knees and headband! Jack, I don't want this night to end, and I'd love to talk more. If it's ok with you, your home might be better. My children are younger and probably less equipped to process mom dating."

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We sat on a sofa in my living room and talked about fun things we could do.

"Sammi, I want to do things together, but at some point, we will want to involve our children in some activities together."

"I agree, but I want us to be more certain about our relationship first. I worry about involving any children in a breakup they might feel responsible for. However, one experience I have not provided for my children is camping. It would also get them away from electronics for a couple of days."

"I like that idea a lot. In the meantime, what can we do together?"

"How about a picnic in a park, or renting a boat on the lake and having a picnic there? We could hike around the lake."

"I like those. Do you think it's too soon if we had a picnic at the park tomorrow? I really don't want to go through an entire week of longing to see you again."

"I feel the same way. Tomorrow is perfect, and I'll prepare the food for our picnic. What time do you want to pick me up?"

"How about 11?"

"Perfect. Jack, this was my best first date ever. I think that's a good sign."

I put my arm around her, and she put her head on my shoulder. I noticed I was able to look down the front of her dress. It was a wonderful view, but I thought a different position might be more appropriate.

"Would you mind turning this way, so you lay across me? That way I can look into your eyes."

"Did you just turn down a look at my boobs?"

"I suppose I did."

She turned and I held her with both arms. We looked into each other's eyes--and kissed. It was a long first kiss. Sammi moaned.

"I was sitting here hoping you would kiss me tonight. I was also a little scared."

"First time kissing another man?"

"Yeah, but it felt wonderful. Can I ask a question about something you said in your office?"

"Sure. What did I say?"

"We were talking about my skin color, and you told me I was beautiful. Then you said something about not confessing thoughts you had of a more personal nature. Do you remember that?"

"Yeah... Ummm..."

"You just turned red! You're embarrassed! Have you wondered about the color of my skin in places not normally visible?"

"I know I'm just turning more shades of red, but yes. That's what I was getting at."

"Interesting. On a different subject, do you prefer milk chocolate or dark chocolate?"

"I grew up liking milk chocolate, but now I prefer dark, no higher than 75% cacao. Why do you ask?"

Sammi sat up and put her mouth to my ear.

"The next time you eat some dark chocolate," she whispered, "that's the color of my nipples."

"What if I had said milk chocolate?"

"My areolas and my lower lips."

We kissed again. This time our tongues introduced themselves and got well acquainted by the time we needed to breathe again.

"Whew! Jack, you are having quite an effect on me."

"Same here. We should probably call it a wonderful first date and get some sleep. I'll see you at 11, but in the meantime, I'll have sweet dreams about kissing you tonight, and dark chocolate melting in my mouth."

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I dreamed about Sammi that night and woke up with an erection. It was only 6 am, but I was not likely to sleep more. Not with her on my mind. I could still smell her perfume.

I made a light breakfast for myself and then showered. I skipped shaving. It was Saturday!

I was at Sammi's home at 10:45. She was ready, and a cooler was on the driveway.

"Morning, Jack. Did you dream about me last night?"

"I did. How about you?"

"I had a wonderful dream that we were walking somewhere holding hands and stopped to kiss."

"Did you run away at that point?"

She was laughing. "No way! I had my hand on your butt pulling you tight against me. You were hard. It was a hot dream!"

"Have you given any thought to our next date? I assume there will be a next one."

"Jack, I have something to confess. I'm already addicted to being with you, and I don't want to wait until next weekend, but we can talk at the park."

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When we arrived at the park, we were not quite ready for lunch, so we left the cooler in the car and walked down one of the paths through the park.

We were holding hands.

After about 10 minutes, we came upon a bench, so we sat.

"Jack, I have something important to talk to you about, but I'm a little scared to bring it up. Would you put your arm around me?"

"I'm happy to. Fire away. Surely you must sense I'm not likely to run away."

"I know, it's just that this is a big deal for me. When Bill and I fell in love, I wanted to have sex with him, and he knew it. One night we sat together, much like we are now, and he said he wanted us to wait until marriage.

"He said he wanted us to be able to teach our children the safety and peace of mind that would come from waiting. No unintended pregnancy. No being taken advantage of and then dropped. No unwanted reputation. And so on.

"Then he said, our love would be more special if we waited. It made so much sense to me, so we waited. Our wedding night was incredibly special.

"Jack, I know you worry about Allie. It's one thing to tell her what she should do and not do. It's another thing to tell her to do what you did. Same thing for me and my two children."

She stopped talking and turned her body to look into my eyes.

"Jack, do you love me enough to wait if I ask you to?"

I kissed her.

"Sammi, Abbie asked the same commitment from me, so I'm happy you brought it up.

I want you to know I'm not pretending to love you so I can get you into bed. Everything you've said makes sense to me, and I want to be able to say that to Allie! I think we will need to make some rules for ourselves, so we don't make it impossible to resist."