How to Have (and Ruin) the Perfect One-off Date

There comes a time in a woman’s life when she wants to have some romance, but she doesn’t want a relationship and she doesn’t want to drag out the connection. This can be accomplished in a number of ways. She can turn to a “friend with benefits”, she can chat up an actual friend she has had her eye on, or she can go to the internet and land a date.   Often times these strategies can go horribly wrong. Your friend with benefits wants to become more than friends. Your actual friend gives you the cold shoulder. Your internet companion flakes on you before you even have a chance to meet up. However, every now and again the stars align and the perfect opportunity for a one-off date presents itself. Ladies, please take this opportunity.

Viv: I had the perfect one-off date last week with Steve. You may recall that I went out with him a while back and we discussed our ethnic ambiguity over a few drinks. Well, after a couple weeks of sporgulating (he is not a prompt texter) I managed to get him out again on a quiet Wednesday night in the neighborhood. He was aware that my time in town was limited, and after some mild chit chat about race and pornography he asked me why I wanted to spend some of my precious last moments in town with him. I wasn’t expecting this question and so I hemmed and hawed a bit and said that I just liked meeting new people and that this kind of behavior wasn’t unusual for me. After a bit more thought I added that I was having pretty emotional goodbyes with my friends, and that it was a pleasant diversion to be out with someone I didn’t know well. In sum, I could have fun with him without crying and enjoy the city I love so much. He let it go after that.

After a couple drinks he asked if I wanted to go for a walk, and while crossing the street a few blocks later he asked me if I wanted to go have a beer at his house nearby.   We both knew what this meant.   He added that I didn’t have to come home with him if I didn’t want to, and I replied that I was aware of that, but I wanted to go anyway. So we went to his place.

And here the date took an unexpected turn to the romantic. Steve’s house is not your usual bachelor pad full of random furniture, dirty dishes, and big screen TVs. It was a beautiful home with lots of comfortable and amusing features as though it had been decorated by a precocious middle aged Italian lady. A few of his roommates were home and they were in the mood to hang out, so we had a few beers on his large back patio. It was odd enough to actually hang out with real people in a relative stranger’s home (as opposed to making an immediate retreat to the bedroom), but odder still, Steve brought out guitars, and he serenaded us with his favorite songs from our 90’s youth. He doesn’t have a great singing voice, but this didn’t stop him. He was genuinely charming. It didn’t feel like a show for my benefit. It felt like a sincere moment of shared enthusiasm amongst friends. We all laughed.

After his roommates went to bed a few hours later we made out in the kitchen. He was a warm kisser. Then he showed me his room, and then we had sex. It was short and sweet and comfortable. I realized I didn’t want to stay the night and wake up with him at 6am (when he had to be up for an early meeting), so I told him I liked him, gave him a few kisses, and hopped in a cab. I smiled all the way home and texted him goodnight.

Sloan: Three years ago, I met up with this British advertising guy, let’s call him Jack, after we messaged back and forth a few times on OKCupid. He was incredibly funny and smart and handsome. We hung out at one of those places in NYC that don’t have a sign on the door and you have to know about it to even notice it’s there. For the whole night, Jack kept me laughing. Our conversation ranged from what stand-up comedians were our faves to how most ads are just god awful to his sneaker obsession to our worst first-date stories. By the end of the night, it felt like we had known each other for years and were good friends, even though we had only met a few hours earlier.

When we left the bar, neither one of us wanted to go home yet, so we went to a pizza place. At some point, over our pepperoni and veggie slices, he boldly said that he wanted to take me home, but that he had friends visiting from Italy and flopping on his couch. We had a short conversation about where we were both at in terms of relationships (neither of us wanted anything serious) and what we wanted (good conversation and good sex).

I took him home and we had some of the hottest sex I’ve ever had in my entire life. I’m serious about this. Because we connected so well, we both relaxed and thoroughly enjoyed ourselves. There was no awkwardness or self-consciousness – just pure pleasure. He slept over and we had morning sex, which, as a side note, I’m not usually that into, but for this guy I made an exception. (I’m tempted to describe the sex because it still stands out in my mind, but I won’t because that’s not the type of blog this is….but suffice it to say, Jack was what my friends and I used to call “sex on a stick”.)

When he left, I remember thinking: “I’m probably never going to see this guy again.” And while I was mostly OK with that, I did feel a little bummed out. The sex was too good not to want a second experience. But it was clear that Jack and I had just had the perfect one-off date, so I wasn’t surprised when he sent me a cute thank you text and then I didn’t hear from him again.

Analysis:

Why are occasional one-off dates a good thing for our egos and how do you have one?

A good one-off can accomplish a number of tasks at once. It can remind us that we are interesting and attractive people. It can remind us that we are capable of engaging the attention of another for a few hours and of being engaged by another. It can make a drab week more exciting. The sun shines a bit brighter the next day. Food tastes better. And, most importantly, it can show us that we don’t need the promise of an extended relationship to trust another person in the moment. We can let go of our apprehensions and relax in someone’s arms, even if we may never see them again. This helps us chill out when we do finally meet people we want to see more regularly and seriously.

There is no one way to set up a perfect one-off, but here are some ideas: Choose a man you like well enough, but not someone you know well or someone from whom you have any expectations of long term romance. It helps to make sure this person is not someone you normally see in your regular life. Realize that you will likely never see this man again and be OK with that realization. Once you are on the date, be open. Make sure the person knows you are not expecting a relationship (Viv: I had a natural out because my move was immanent. It may be slightly more difficult to say “I don’t want a relationship”, but I am sure there are charming ways to make this clear). Make sure to share enough about yourself to make the person feel comfortable and relaxed. Don’t hold back, but don’t promise more than you are willing to give either. Be romantic yourself or let the other person be romantic with you. Do the goofy thing that seems silly but is actually fun. Go for a walk, sit next to one another in a booth instead of across from one another. Sing. Have dessert. And when the time comes, kiss with feeling and don’t be shy. Look them in the eye. At the end of the experience, thank them for their time and let them know they are appreciated, even for a very brief moment of connection.

Once you are gone, keep further communication to a minimum and remember the experience fondly. And whatever you do, don’t let yourself daydream about this person. Don’t imagine any “future” with them. It’s also not a fantastic idea to try to repeat the perfect one-off date. It’s a one-off for a reason. Just enjoy it for what it is.

Viv: Since this date with Steve I am currently having a case of the “do as I say, don’t do as I do’s”. It was a perfect one-off. I was grinning from ear to ear and I did not text Steve afterward…..until he texted me a few days later to ask how my packing was coming along. This threw me off. It was a one-off! Why is he texting me? And why is he texting me with something so benign? I assumed he might be putting the feelers out to see me again, but I wasn’t sure I wanted to ruin the glow from the last date. So I replied with something equally innocent and then started sporgulating. He didn’t reply for two days, and when he did it was only a bland description of his weekend. But by then I had been thinking about seeing him again, and I decided it wouldn’t be a horrible thing to try and fit him around Doug in my last few days in town. I had some windows open in my schedule, and so I texted him to see if he might have a window that could overlap with one of mine….. And now we are possibly going to meet up tomorrow.

I may have ruined this one-off for myself by asking for more. In the future, I will resist the urge to extend a perfect one-off with a man I don’t want to seriously date and just let it go without suggesting a future meet-up. My ego shouldn’t need more attention after one sweet date. But for now, I am sporgulating again, and really looking forward to another round.

Sloan: Jack is back. About a week ago, we got back in touch (oh, the joys of the internet era) and have been texting back and forth a little. He remembers every detail of that night we spent together and maintains that it was one of his best sexual experiences as well. Now that we’re both single again, we’re tempted to get together and do it again (and again and maybe again). But I’m worried that if I go out with him, I’ll get too attached. I’m not in the same situation I was three years ago and he’s still smoking hot and very funny and really smart and creative. I’m also not sure I want to ruin my memory of our perfect one-off date. There’s a little bit of pressure there now, built up over years of remembering that night – and each other – fondly. Then again, I’m not sure I can resist the temptation to go out with him again. If I do, I’ll be sure to post about it though (Viv: oh yes you will.  And what gives about not being into morning sex? That is the only reason to sleep over!).

Dating After Divorce

Divorce.  Ugh.  Oof.  Sigh.  This experience comes in many shapes, sizes, and bittersweet flavors.  It can be positive and empowering or devastating and crippling, or more likely some confusing combination of those feelings.  No one has the same experience of divorce, and there is no magic solution for recovery in terms of jump starting or easing into your romantic life and moving on.  And yet the urge to connect with another person often rears its head at some point in the process of separation and disentanglement from a life partner.  Or the urge to have sex with someone who is not your spouse.  Or the urge to pay attention to something beyond your pain.  Whatever the motivation, we have found that dating after divorce is not at all the same as dating before we were married.

Viv: I was married for 2.5 years before I separated from my husband, let’s call him Harvey, though we were together for nearly 5 years.  All told it was a brief relationship in the scheme of marriages.  And yet the experience was still the most painful and challenging of my adult life.  In many ways I am still in recovery.  My official divorce is still pending and it is likely that I will be grappling with issues of trust for some time to come.  I have been separated for 10 months, and I have not seen Harvey in all of that time.

When I first met Harvey I was in transition.  I was in my late 20’s, fresh out of graduate school and about to embark on an adventure across the country in a new city at a new institution.  The world was my oyster, though if I am honest, I still harbored feelings for my recent ex-boyfriend (another 5 year relationship), and I was apprehensive about what the future would hold for my new life.  Harvey was my 8th date on a 10 date challenge I was doing for fun with my friends.  I didn’t think too much of him when we met.  He was handsome, but also a bit squat, hairy, and he seemed more nervous than most of the men I was dating at that time.  I would later learn that he suffered from anxiety and crippling insecurity, but back then I was puzzled by his nervousness.  He seemed to compensate for it by being overly enthusiastic about me, about my life, about my family, and about my friends.  He gushed about every aspect of my existence.  Despite my initial annoyance with this behavior I was flattered, and I let his desire for me sweep me away.  We began a cross-country relationship.  I discovered his adorable sense of humor and his deep seeded need for stability.  This seemed to match my own goofy sense of humor and love for family, friends, and community.  We fell in love, and I forgot about my initial reservations.

Harvey and I had a healthy relationship for 3 years, including our first year of marriage.  This is in large part because we lived on opposite coasts for most of this time, and when you have a lot of space from your partner you relish the time when you do see them.  We thrived in a way.  We did our best work.  Harvey’s commercial career in tech exploded.  I published in a top journal.  But after a while, despite my efforts, my nonprofit career stagnated.  I quit my full-time gig, which seemed to hold no real promise of change, in order to travel back to the other coast to move in with Harvey as man and wife (something he insisted upon), to support his rapidly growing business venture, and to begin to think seriously about starting a family.  What I didn’t quite get (It seemed weirder that I wasn’t living with my husband) was that in the process of moving in with him I became dramatically underemployed and dependent.  I was too naive to realize that this was a dangerous choice.

Our world rapidly fell apart after I moved in for good.  I was voraciously independent so I never felt comfortable with our arrangement, and Harvey did not have the capacity or maturity to respect someone who was circumstantially dependent on him.  We began to fight severely and frequently.  He stopped supporting my goals, he ignored my contributions to the household, and when I was lucky enough to win a prestigious research grant to temporarily work overseas, he was irate about it.  He felt that I wasn’t doing enough to support his stressful career choices and that I would essentially be abandoning him.  I left for the research anyway (after cutting the time I would spend abroad in half to try and accommodate him) in order to hold on to my career dreams.  He began to spend a great deal of his time with a younger female friend of the family (someone I introduced him to and who attended our wedding).  By the time I came home for a visit after about 6 weeks away they had already admitted that they had feelings for one another.  The marriage never recovered (despite counseling), and Harvey left me soon after my research season ended.  Yes, he left me.  I was too stubborn to quit and I was determined that I would not be the one to say the words.  I moved out after they were finally said, and a few months later I found out what I had already suspected: he and our friend were in a relationship.  He officially filed for divorce last month.

The feeling that you are losing the person you love (or in my case gaining the realisation that the person you loved and the person in front of you now are two very different people) is viscerally like having your internal organs ripped out one by one and smashed on the cement combined with the numbing sensation that you are watching all of this gore and violence from a great distance.  Your whole world is shattered.  You implode.  I also lost his family, my own family was hurt and confused, and my community of friends was thrown into turmoil.  The dust is still settling.  I have never wept so much in my life.  It was the kind of grief that consumes your whole body as when someone you love dies.  I gained new wrinkles and gray hairs.  In truth, I may never look the same again.  I have been forever marked.  It was a brutal initiation into adulthood and the unpredictable vicissitudes of life.

Sloan: I want to pipe in here to say that I’ve been divorced twice, but didn’t experience what Viv did. In both cases, I was in an open marriage and was dating at the time I divorced, so my experience is of a different, but equally complicated, sort. That being said, I am 5 months out of a relationship with someone. We lived together and I loved him desperately. When he walked out on me, I felt exactly as Viv describes so beautifully above – I was devastated and broken.

Analysis:

How will you know when you are ready to date again after your marriage ends and why is it healthy to do so?

As we mentioned, there is no formula for moving on from divorce or the end of any serious attachment relationship.  Each person has different needs, fears, and expectations.  The worst thing you can do is leapfrog from one bad relationship into another, or use another person as a security blanket to compensate for your loss.  That said, if you are in a healthy mental state, you are ready to move on, and you are wise about your choices, you can gain a lot of perspective from practice dating.

Practice dating is simple: You go meet someone for a beer or coffee, you chat with them, you flirt, you ask questions.  The point is to reflect on your own reactions to this other person’s mannerisms, behavior, opinions, and attitudes.  After the date you take time to assess a number of factors.  What annoys you about this person? What reminds you of your ex? What do you like about the person and why? Where are your points of vulnerability and anger? What are the things you find you most have in common with another person?  What are your own behavioral responses to the other person and why are you having them? How does it feel to be out on a date? In essence, practice dating means seeing a number of people while constantly reflecting on the experience, learning what your trigger points and needs are, and figuring out how to move forward via trial and error.

Sloan: Many people will weigh in on whether or not you *should* be dating after a bad breakup. I am of the opinion that those people are talking about themselves, not you. There is no magic number of weeks, months, or years. Every person is different.

For Viv and I, it has been important to practice date for the moment we’re ready to really be in something again. For others, they need solitude. Either way, dating again is tricky, but I for one am back on the horse.  (In a future post, we’ll explore trust issues and what it’s like to have sex again after a long-term relationship.)

Viv: Remember, there is always a bright side.  I don’t have to be committed to a man who doesn’t respect me, my dreams that I have tirelessly pursued for years, or the community I have worked so hard to build in the world.  I don’t have to be married to his insecurities.  I get to date again, and feel beautiful and sexy in spite of, or even because of, my new wisdom and new wrinkles.  I moved out of our apartment, and 3 months later (thanks in large part to the support of my incredible family, wonderful friends, and amazing therapist) I was on Tinder, swiping for fun.  A couple weeks after that I met a jolly man I could joke with, and we went out a few times and slept together on one warm Saturday night.  I also started dating 2 other men about that same time.  I only told one of them about the separation (he had gone through a divorce years ago so it felt safe).  Now I date all the time without commitment (something I never would have done prior to this marriage, when I was essentially a serial monogamist).  I experience real joy.  I can’t handle a committed relationship yet, but I am practicing for the time when I am ready to be vulnerable and welcome someone into my life.  In the meantime, there is laughter, learning, and sex.  I value these fleeting moments of companionship.

I may never see Harvey in person again.  That is sad considering how close we once were, but he earned his absence from my life.  The good news is that I landed another (much better) full-time position in a new city back on the other side of the country, and I am moving in weeks.  My independence has been restored.  My senses of identity and of my relation to the rest of the world are stronger than ever.  I’m back.  Brace yourselves.