If you’re not laughing and having fun together, then you’re not doing it right.

Summer time is just about here, and I have kicked up my dating activity a few notches or so. For the past year, I have been on a couple of dating sites, with mixed results. A lot of endless conversations that go nowhere, a LOT of first dates that don’t turn into second ones, a lot of guys who ‘just want something casual” (i.e., to sleep with me once, and then ignore me forever – no thank you), 2 short-lived relationships, and a couple of dates that turned into friendships. So, while ultimately, I am looking for the real thing – love – I am quickly finding out that this dating thing is a numbers game. It might take a long time for me to find “the one” who is out there for me. I used to be very impatient about that. Now, I am still a bit impatient, but I am trying to change my perspective and take this opportunity to meet a whole bunch of interesting (and sometimes not) new people. There has also been a lot of kissing, which I have no complaints about. So in the meantime of love coming along, I am taking a positive outlook, and just having fun.

One of these ways to “have fun” in this dating world, is to start a ‘friends with benefits” situation. Now, I’m pretty sure that everyone below age 90 knows what friends with benefits, or “FWB” is, but just in case you have been living under a rock for the past few decades, and there’s no Wi-Fi under that rock so you don’t have any internet access – “Friends With Benefits’ is the term for when two people who are friends, decide to start sleeping together. Now, hopefully you have figured out by now, that the “benefits”, is the wonderful sex that takes place between the two agreed upon parties. Now, I will not pretend that finding the perfect person to have a “FWB” situation with is easy. It’s not. It’s complicated. It is very easy to screw this up. A lot of factors have to be there, in order for this to work. First, you have to both be friends with one another, and also be attracted to each other. Also, you both have to be single at the same time. Most importantly, neither party can have stronger feelings for the other, because once sex gets involved, there is always the danger of falling in love with this person. So you have to be pretty confident that this person is someone you love as a friend, and respect, but that you won’t find yourself confusing intimacy with actual love. So, if all of these parameters are in place, and both parties agree that this is something they would like to do, it can be pretty damn enjoyable. And very satisfying.

My First Friends With Benefits Tryst

Recently, I was texting with a guy I had met a couple of months back on one of the dating sites. We had gone out on 2 or 3 dates together, and although there was definitely chemistry and attraction there, for reasons too boring to get into here, we ultimately decided that a long-term relationship probably wasn’t in the cards for us. So we decided to stay good friends, because we do like each other. And then one night, we started texting back and forth about our turn-ons, and just sort of being lightly flirty with each other. And then he said: “You know, it would probably be really good if we ever slept together.” And then I found myself saying: “I could go for that.” To which HE said excitedly: “Really???” To which I said: “Hell, yeah. Friends with benefits. I’m single right now. You’re single right now. Why not?’ And our FWB was born. A few days ago, we had our first ‘tryst’, when he picked me up and invited me to spend the afternoon at his home. We had a really great time, and plan on doing it again fairly soon. So, if you can find the right person for this, and it is tricky to do that, it can truly be a blissful thing. Here are 5 reasons why:

1-SAFETY AND MUTUAL RESPECT

Sure, one night stands can be hot, in theory. In reality though, having sex with a total stranger that you just met and don’t really know at all, is actually potential for something quite dangerous. You could be dealing with a stalker or a creep, or someone who might force you to do things you aren’t into doing, or just someone who doesn’t share the same turn-ons as you do. This is one of the great benefits of FWB. When you are friends with the person you are about to sleep with, you actually care, really care, about what turns them on, and what doesn’t. My friend and I spent the couple of weeks before our tryst, texting and calling each other to find out more about what the other likes. He flat out asked me: “Okay. So tell me everything that turns you off, so that I don’t do anything you don’t want to do.” We told each other: “This is what I like. This is what I don’t like.” (We found out that we both hate feet, which was humorous.) We started to build up the foreplay for weeks, sharing sexy images with each other through texts. It was lovely, and very arousing. So when it came time to get to the fun part, it was wonderful. Having sex with a friend is a great feeling, because the entire tone is always filled with respect, and you know and trust each other, and when you know this person would never bring harm to you, then you are willing to open up even more, and be more adventurous in bed. Which, for me, is something I could never do with a total stranger.

2- NO STRESSFUL RELATIONSHIP EXPECTATIONS

This might be my favorite part of the FWB thing. Yes, being in a committed relationship is a wonderful, beautiful, and lovely thing. But there is something to be said for just having some intimacy, simply because it feels good and feels nice. And not having to feel guilty about that. It is pretty cool when you are comfortable enough with each other to get vulnerable and get naked, but you don’t have to think about ‘where your relationship is going” with this person, or how you can’t stand their mother and that will never change, or whatever else. FWB takes all the stressful parts that sometimes happen as a result of sleeping together, out of the equation. It’s a truly beautiful thing.

3-YOU ALREADY KNOW EACH OTHER’S “STUFF”

Friends have most likely, at some point, had long talks about each other’s pasts and insecurities and whatever else. In this case, my friend knows that it had been 7 months since I had slept with someone. He also knew that I am not in good shape and overweight, and that I feel extremely self-conscious about him (or anyone) seeing me naked. He also knows that I have been through a sexual trauma, and so there are certain things in the intimacy department, that are ‘triggers” for me, and bring me right back to that night. So he knew to stay away from those things, because it would not be a fun experience for me. Because we are friends, we had discussed all of this leading up to our afternoon delight, and it made a huge difference. I also knew things about him, which I won’t say here in order to protect his privacy. By knowing these important things about one another, it made the sex so much more carefree and open. We were both able to fully relax into it, and into the knowledge that we had each other’s backs.

4- You Can Discuss PRE-GAME

When getting ready to have sex with someone you don’t know well, (one night stand situation or just casual sex with a date) you are probably much too nervous and anxious to include laughter as part of the equation. And when you are being intimate with someone you are in love with and in a relationship with, sometimes that can turn into a lot of intensity that makes the sex feel very heavy and serious. And that is great. But there is something to be said for sex that is just really FUN. The kind of sex where you are turned on and being silly, at the same time. Where you can laugh easily, and just generally be at ease throughout the event. Our tryst this past weekend, and everything leading up to it, was very much this way. A few days before our intimacy, I started to get really nervous. So I decided to just tell him that. I sent a text saying: “I’m really nervous.” He asked me why, and I said “because its been awhile, and also I don’t feel comfortable naked. I don’t feel sexy or attractive right now.” He assured me that he would do whatever it took to make me feel wanted and sexy, and that he would do whatever I needed to help me relax. So that morning, I sent him a text, which was basically a list of what I required in order to feel relaxed and less self-conscious. First, I didn’t want to be naked and show all my fat and stomach rolls, so he suggested that I go in his bathroom once we get to his house, and change into whatever makes me comfortable. I decided on a long thin button down black sweater, and undies. Next, I told him to please put the air-conditioner on in his bedroom, because I didn’t want to be sweating profusely while being intimate. That is NOT sexy. Then, I asked him to please pull down the shades and make the room as dark as he could. Lastly, I wanted a shot or two of whiskey before we began. Our text exchanges when coming up with all of this, was beyond hilarious. He adhered to all of my demands, while also making funny as hell comments in the process. “I have a liquor cabinet, and I’ll make you whatever drink you like, but I have to say no woman has ever required downing shots before bedding me.” When we walked into his bedroom, he shivered and said: “Jesus, it’s freezing in here!” Then he made comments asking me if it was dark enough for me, and that if he made it any darker, we wouldn’t be able to see what the hell we are doing. I couldn’t stop laughing, and this set the tone for the afternoon, which was equal parts very hot, and also extremely fun. And because he was kind enough and patient enough to put up with my weird requests, which I thanked him for multiple times, I WAS very relaxed, and I had such a great time. I joked with him about how hilarious it is, the things a man will do, in the pursuit of getting laid. “You ain’t kidding’, he laughed back. Personally, I think sex should be a ton of fun. If you’re not laughing and having fun together, then you’re not doing it right.

5- AFTERWARDS, A DINNER DATE

So after being in bed all afternoon, and having multiple orgasms, courtesy of my awesome friend, he turned to me and said: “I’m starving. I’m taking you out for dinner.” Who is a fat girl to argue with a nice dinner? So, he chose a really nice steakhouse, and off we went. He ordered prime rib, and I had one of the best Rib-eye steaks I have ever eaten in my life. Salads, dessert, wine, champagne, and wonderful, post-bliss conversation. I got to enjoy myself for an entire day, with someone I respect and truly like, and I didn’t have to feel like I had sacrificed any integrity or self-respect to do it. In fact, it felt good. It felt well-deserved. It felt great. We were proud of ourselves, and we were happy. The best part of great sex with a great friend, is this: We held our glasses in the air, and we made a toast. “Cheers. To us. To feeling awesome. And to a successful afternoon. We had a good day.”

I can’t wait to do it again.

Next time, I might even let him keep the lights on.

And I’m definitely ordering lobster.