So, I’m coming up on being separated for 9 months now with no real divorce in sight (that’s a whole other blog). With several months of dating under my belt, I realize being “single” means different things to different people. Let’s jump into that one.

Rule 14: Set Your Own Expectations and Limits on What You Want

I think the more I’m out here being single, the more I’m exposed to the great variety of potential relationships in this world. As I’ve written before, I come from a very Catholic-based values mindset. With that, I was raised to think of romantic relationships as 100% monogamous, committed, and really for procreation – families. Now, I do not fault my parents or family for fostering that type of mindset. In fact, I do believe having a firm background in something allows for you to compare and explore the world around you more once you are comfortable actually exploring. However, as I mentioned in the sex post, it takes a Herculean effort sometimes to think outside of the box when it comes to relationships. The truth, however, is there are a multitude of ways to relate to others and really no defined way of doing it. Yes, there are religious and tax implications to relationship decisions long term. Yet, in the short run, I’ve kind of enjoyed the ability to be flexible in my world view.

I’m going to run through just a few options out there that you run into when you are single and actively dating/engaging others.

Conventional Dating – This is what most people want to hear about. Boy Meets Girl or Boy Meets Boy or Girl Meet Girl, whatever combination. The two go on some dates, like one another and then decide to lock in to an exclusive relationship with that other person (I’ll do a whole separate post on Exclusivity at some point). Conventional Dating naturally would lead to eventual partnership and potentially a marriage or long term relationship with real commitments – children, a home or formal marriage ceremony. I think most people out there in the world assume this form of Dating, and want the Happily Ever After like the movies. However, there are a lot more permutations.

Friends With Benefits or FWB – This is more and more common these days or it always has been but now it is in the mainstream consciousness. The idea here is two people like one another sexually, typically, and they decide to have sex on a regular basis or even on an on-call basis with no actual commitment or exclusivity. Why would someone do this? Well, people got needs…. and in lieu of getting emotionally involved with someone you may not care about or are unsure about long term, then getting regular sex is nice. FWB can lead to a conventional dating situation or it can end quickly if one of the people becomes exclusive with someone else. A short story here, I did formally try this once in my last single stint. I had dated a woman a bit, and really liked her, but as I often do, I held back on having sex (since I wanted to see if a relationship was in order first, yeah stupid, I know). After we lost touch, she reached out after a few months and stated clearly if I was open to “Benefits” which I said, “Sure!” We got together a few times, which was great fun, but typical Catholic me f-ed it up when one time she got sick – a cold. I stopped by with Chicken Soup, since I wanted her to feel better. Well, that violated the FWB code and I guess I was getting “too attached.” We never hooked up again. She got engaged about 6 months after that. I guess I was just a stop gap. Good for her. Lots of people have that person they turn to when they want some, and there’s nothing wrong with that.

Sugar Daddy/Mama/Baby – I went over this basically in another post, but to refresh, there are a lot of younger people that enjoy the stability and financial benefits of being with an older person (typically the older person has the financial stability). The two engage in sexual contact, but unlike FWB, there is an actual financial benefit/support to the typically younger party. In this “arrangement,” both parties can get what they want, however the dynamics of this can be challenging. Plus, the arrangement does not always include exclusivity or the prospect of a more long term/conventional relationship. As I’ve written before, I don’t think there is anything wrong with this type of relationship. However, like all of these situations, communication about what you want is pinnacle (more later).

Polyamorous Situations – In this situation, you enter into an open style relationship knowing that the other person is involved with other people sexually/romantically/energetically. I have encountered people openly Polyamorous often in this current single stint, especially with women I’ve met under 30. Sometimes, those women have also been openly Pansexual, which is attracted to anyone – man, woman, and transsexual.

Friend Zone – The last possibility I wanted to discuss is the Friend Zone. The Friend Zone is when you are interested in someone romantically, but the other person does not consider you the same way. So, there can be a lot of tension arising between these two as the expectations may not match or often times the timing for what the 2 people need are mismatched. Now, most people consider the Friend Zone a negative place. “Stuck in the Friend Zone” is the term. If you are constantly being disappointed, then I suggest making your feelings known. It risks the big hurt, but nothing ventured, nothing gained.

Friend Zone Can Be A Safe Place

Now, there are many more possibilities here, but I think you get the idea. The rule states that “Set Your Expectations and Limits on What You Want.” That is the key to all of this. If all you want is Conventional Dating with an eventual Conventional End being Marriage, Children and a Home together, then by all means put that out in the world. Be clear about it in your profile, on your dates, talking to your friends.

However, any one of the situations listed here can work with open communication – Rule 12 – Straight Forward Communication. The worst thing that can happen if you are direct and honest about your expectations and feelings is you get the answer you don’t want to hear. However, at least you know where you stand. It takes emotional courage to have such a discussion, but if it doesn’t go your way, then there are more people that will meet your expectations within your limits.

Remember, being single is just that, you are a Free Agent. You can do whatever you want to do. The trick is knowing what you want.

Ok, on to me right now, and I’ll keep this brief. As a guy leaving yet another marriage of now 7 years and relationship of 9 years, I’ve approached dating and being single very differently than in my 20s or 30s. At the moment, I’m figuring out what I want by exposing myself to almost all of the situations listed.

Conventional Dating: Of course, you know these posts are Dating By Wegs, so I love to go on dates, meet new women and explore the city. The only rub here is that I’m not 100% ready for the eventual goal of being in a committed, monogamous relationship right now. I know full well that at some point I will. However, I have tended to lock in early in the past and that has led to 2 failed marriages. I’m still trying to figure out why those failed and despite my unfailing belief in Love, I am taking a bit more time to give my full love to one person today.

FWB: I have not had any formal conversation with anyone about this one this time around. However, keeping things casual and getting regular sex definitely appeals to me. Maybe I’ll pursue this in the future.

Sugar Daddy/Baby – I’ve been on the cusp of this over the past several months. The truth is I’m like a Junior Daddy, as I just don’t have the financial strength to do this. Again, I see the benefits here, but I am much better at supporting someone emotionally than financially. Most people look down at this situation as a form of prostitution, which I can see that perspective. However, my experience is more of helping someone you care about when they need it over a transactional relationship. The challenge is setting that boundary and I expect more from someone I care about, and as such, it is not really for me.

Polyamorous – From a Catholic guy, this concept has honestly blown my mind a bit. I get it intellectually, and as a single guy, it really appeals to me that I can be with whoever I want. Yet, I still have not been able to completely buy into this approach, as I have not been able to emotionally be strong enough to be one of many which I will openly admit is hypocritical. On the flip side, the women I have encountered like this have been much more in touch with their sexuality, which as stated before, really connects with my “Sexual Being” side of myself. Oh the internal conflict!!

Friend Zone – I can speak with experience here that I have had woman I was very interested in and when the possibility of a Conventional Dating or Sexual Relationship of any kind was not possible, then I never heard from them. I would much prefer to have a continuous relationship with someone at some level over all or nothing. At the moment, I’m fine being friends with women because I do not have expectations for more and unlike the perception of the term, deepening a friendship that could lead to more is actually really appealing given my past failures.

So, this post is one of the first that I am not really following the rule 100%. I am figuring out what my expectations and limits are right now. I know the extreme limits – no SD-SB, no Poly, not ready for Commitment in Conventional Dating. However, the gray areas within all the rest is still wide open. For me, being more open has worked out to learn more about my limits and not be closed off to people I may not have met. After all, meeting new people is fun to me.

For yourself, as you date and go out meeting people, the goal should be to figure out what you want, expect and your limitations. Once you know those, then clearly communicate those and you will get what you are looking for coming back 100 fold.

Wegs