How to be my Boyfriend

Reading time: 8 – 12 minutes


I am 39 years old now and I have never dated. I’ve never had to date. I just sort of bumble along and enjoy life, then suddenly I meet a guy with whom I connect strongly and then we discover we’d make great boyfriends and we give it a shot (and then I get dumped 10 months to 4 years later). That’s been the way I have found and held every boyfriend relationship, so far.

I’ve never been one who could “date around,” or go out with one guy tonight and another tomorrow night. It’s not that I have a weird judgment against dating around, but just that I don’t know how to do it very well. I think my heart is too sensitive, or something. I just feel really uncomfortable with the idea of “shopping” for a person, and I prefer for it to happen more organically; unexpectedly. I like the surprise of a wonderful rapport, rather than the search for it. In the meantime I get to work on myself in a way that may make me an even better boyfriend for someone, as well as being a better person for myself. So, “dating,” to me, reduces the magic of personal growth and surprise of life to an interviewing process of distraction from self, and is not a natural exchange for me.

Dating around means someone is going to be potentially chosen and many are going to be potentially rejected. I like neither of those options; at least, not with such an emphasis. I’d rather an experience of emergence, discovery, and playfulness (and potential friendship) than an experience of interview and assessment. The interviewing and assessment is going to happen, no matter what, so I’d rather it just be a gentle undercurrent than to have it to be the focus.

Even when I’ve met someone from online for a “date,” I always explain that my first meeting can’t really be considered a date. It’s just a meeting. It’s just a chance to hang out and get to know each other and focus on a friendship and from there we can THEN decide if we’d like to go on a date. I’d rather meet a potential friend than to lose that possibility because we are incompatible as boyfriends; I’d rather make a date with someone in person than to make a date with someone I’ve never met.

I don’t know why I prefer all of these things, but it’s the way I work.

Another thing I’ve always preferred is to never be too rigid in my expectations and wishes for what I would want in a mate. All of my fundamental basics that make up my identity are kept as MY fundamental basics and not something to wish from someone else, or to impose on someone else. I’d rather discover the fundamentals about another person and then create a unique world of combination. For the most part, my most successful and fulfilling relationships were rooted in the mutual respect and exploration of our different identities, even when fundamentals were at odds to each other.

SO… for 20 years of my life of relationships/dating I’ve not “dated around,” and I’ve experimented with flexibility of fundamentals….

….and now I am ready try something different.

I still don’t think I can date around (I just don’t have that in me), but I want to enforce a few things that I would consider “fundamental deal makers,” instead of being so flexible. In my flexibility, I find that I become very willing to be the invisible person in the relationship. It’s a certain sabotage that I’ve found in me as a pattern. It’s not that I deny the things that are fundamental about me, but that I feel a strength in my being able to set mine aside for the importance of someone else’s. While this IS a strength to some degree, it is also a contributor to the detriment of a relationship, because when your relationship with yourself becomes compromised by your emphasis on your relationship with someone else, you cut off your own air. You clip your wings while encouraging the flight of another.

And then you wonder why they leave.

So… I’ve decided to gently hold some of my fundamentals in strong consideration when a potential boyfriend now comes along, and that includes my current relationship that has blossomed out of nowhere. This is 20 years worth of experience that has helped me to discover what is truly important to me and I’m also secure enough with myself now that I don’t really feel a need to be so compromised in order to have a relationship. I’d rather be free and single than to feel lonely and invisible in a relationship. I’d rather keep my relationship with myself as healthy and whole than to divide myself into something more digestible for another person.

I’ve thought about this a lot.

Some people call these things “deal breakers,” but I’m trying to emphasize the more inspiring angle of “Deal Makers.” The more deal makers being fulfilled in a potential relationship, the more likely that relationship could be profoundly fulfilling for both of us. I would never IMPOSE these on another person, but I am brave enough now to let that person go on his merry way if he is not interested in similar, common grounds.


  • Socially graceful, friendly, and actually likes people
  • Loves reading together (quietly, or out loud to each other)
  • Loves being playful, in general, without thinking he is “too old” or “mature” or “too cool” or “too stupid” for silly playfulness
  • Loves color and brightness and appreciates toys as part of a home
  • Finds laughter to be an intimate bonding factor
  • Vegan, Vegetarian, or on his way to either of those
  • Sees animals as valid, feeling Beings who are not to be exploited, enslaved, farmed, worn, or eaten
  • Questions the very nature of reality and enjoys long, thoughtful conversations about such things
  • Finds benefit in discussing issues that arise as conflicts or differences or insecurities between us
  • Is naturally monogamous and finds that to be exciting, sexual, and sensual, and not a weird, resentful burden
  • Finds it thought-provoking, inspiring, and almost obligatory to question against mainstream conclusions about life, events, and truths
  • Finds insecurities to be something to soothe and heal, not to use against each other, or to feel are burdens
  • Is not religious, but spiritual
  • Is not political, but aware
  • Feels good about considering the impact of his choices on me, and does not feel burdened by that extra step in thinking
  • Does not smoke and understands why it’s a violation to be around it in public (I’ve added this one for two reasons: kissing a smoker is gross, sorry; and if you can’t understand why no person’s habits should be something another person should be forced to partake in, then you probably don’t have a clear idea about appreciating shared space; honoring shared space is NOT the same thing as taking away people’s right to choose and do what they want)

So, those are some of the obvious DEAL MAKERS, but here are some deadly deal breakers, because no matter how much is being fulfilled in my deal maker list, these are the things that can ruin EVERYTHING:

These are words that will stop my relationship with you in its tracks, or seriously derail us to the point of needing a very long recovery:

  • “What?! You have got to be kidding me! Animals are MEANT to be used for food and clothing! Humans are carnivores!”
  • “I really don’t see what the problem is if I feel like kissing another guy or flirting with him in front of you (or behind your back)… it’s JUST a kiss, for god’s sake. And we all need that extra attention from time to time.”
  • “I’ve cheated on you.” (or finding out that he’s cheated on me)
  • “I already know everything I need to know about myself; I’m not really interested in learning more.”
  • “Oh my god, get OVER it!”
  • “I lied to you.”

Those are just a few of the obvious deal breakers, but the list doesn’t include the even-more obvious ones of violating Honesty, Communication, and Integrity, which are basic ingredients to a successful and intimate relationship. If those three things are violated in any way, there is trouble.

And I’d like to point out that I DO understand the need for attention from others, even as flirtation and even while in a monogamous relationship, but there is a way to allow room for that without it being a violation to your honesty, communication, and integrity. I also don’t like the word “cheating,” but I guess it’s the only word to use to describe someone who tells you one thing and then does another thing. If you enter a relationship with me KNOWING what is important to me, and you stand strongly with me to encourage that mutual agreement, and then you cheat (on any level: emotionally, physically, etc), then it’s not about the act, itself, but about your level of integrity and honesty that has destroyed our intimacy. If want to have sex with someone else, then leave the relationship with me… FIRST. It’s just NOT for me to have that kind of a relationship, and I’ve been there, done that, and frankly, don’t need the experience again. You should have the guts to leave me before you would have to cheat on us.

I don’t need to impose my rules on you, but I’ve accepted that it’s okay for me to have some.

So there…

It’s on record.

3 thoughts on “How to be my Boyfriend”

  1. “This is 20 years worth of experience that has helped me to discover what is truly important to me and I’m also secure enough with myself now that I don’t really feel a need to be so compromised in order to have a relationship.”

    What do you mean? I told you not to make yourself invisible! That was me!

    -your abbe (!)

  2. Not that this has anything to do with dating and not that I mean to freak you out about moving to the Netherlands more than you already are, but you may want to get used to that smoking thing and shared space. There is no real smoking ban in Europe (aside from a few countries that have started to impose some laws), and bars in Amsterdam tend to be rather smoked out 😉
    I personally am not a fan of it either (I guess I do subscribe to your concept of shared space), but it is a reality here. James gets almost militant about it (even though he used to smoke cloves cigarettes like a mad man himself and would blow his smoke at people looking at him with disgust).
    Last but not least, concepts of shared space do differ across cultures, and lots of studies have been done about it. Weather and climate in general is supposed to have something to do with, for example….

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