OCD Family vs. Dating Relationships

[Maximus2019]

This is something I should have sought help on years ago, and am finally doing so now.

As a back drop I have a daughter who is 16, and I've been living with her mom more like friends for the last 8 years. We've discussed separating when she is 18 and finished with high school. Over the past three years or so, I've wanted to have relationships with other women. The challenge is that I am still living with my daughter's mom and spend a lot of time with my daughter, and it's hard to be in a regular dating relationship under these circumstances. I took an interest in a lady who did web design for me a few years ago (I'll call her Ella), and we went out on a date. I think she didn't want to continue with me because of my situation, and ended up getting married and divorced.

The second background fact, in addition to the part about the situation with my daughter's mom, relates to my younger brother. He was only 14 when my parents decided to have an open relationship, and they seemed to prioritize their outside relationships over me and my brother (I also have an older sister, but she was in college at the time and not as affected). My brother was affected the most, since I was already 18 which is a less difficult age than 14. Anyways, my brother ended up hanging out with the wrong crowd, doing hard drugs, being in rehabs, almost dying, etc. He lived like this for about ten years. Eleven years ago, though, he stopped doing drugs and hasn't done them since (he still smokes pot, etc., but none of the deadly stuff). He is a legendary skateboarder in our city, and has skated since he was six. I got him into it when we were kids.

Despite my brother's recovery, he still has financially struggled and currently lives in my mother's basement. He's been there for the past ten years or so. Only just recently did we get him new floors and renovate his place. He currently works as a delivery driver for Amazon and likes his work.

My father got re-married and has two children - my half sister who just started college and my half brother who is only one grade older than my daughter. I feel like my father has allowed my brother to struggle unnecessarily. For example, my brother has had a hurt ankle for a while, and my father never offered to pay for him to see a physical therapist. I told my brother to find a PT to help him and I will pay for anything that is not covered by insurance. My father also never offered to renovate my brother's place even though the basement where he was living in was unfinished and had a dusty smell (my mom recently got extra rental income which she is using to renovate). Last June, I paid for my brother and I to go on a skate trip to Colorado- it was our first trip away together without our parents (not including camp), and our first trip away together as adults. I thought that this is something I should do at least once a year which will be good for his health and good for me as well.

The third back drop (and this might or might not be a bit controversial and I hope to separate this part of the post from the part about OCD below), is that to be able to have a relationship despite the situation with my daughter's mom, I realized the best option for me at this stage, at least until my daughter graduates, is to have a "sugar daddy" relationship ("SD relationship) with a woman (I don't like the term, but it's the best way for me to describe it). I offered Ella (after she got divorced), to be in an SD relationship (I’ve never used that term in speaking with her), where I would help her with her rent and other finances as part of it. She agreed and we've been off and on in a relationship for the past 4 years.

Here's the struggle/OCD part which has been my greatest mental struggle for years: I am constantly conflicted about spending money on Ella vs. saving money to secure my brother's future, go on trips with him and my daughter, etc. The struggle also involves me conflicted about the mental energy that the relationship with Ella takes (even though we only meet a couple times a month). For example, my dad has wanted me to help him revise his estate plan, which involves him leaving money in trust for my brother. I feel that if I have a relationship with a woman I wont be able to concentrate on helping him with his estate plan and we will do it wrong. I keep changing my mind on whether or not to have a relationship with a woman where there is a financial component involved (or even if there isn't one). One day I will decide that I will fully focus on my daughter and brother for two years as well as on saving up funds to secure our futures, and only after that can I be in an SD relationship. I will commit to that decision, but a week later will start feeling very deprived. Then I will decide to be in an SD relationship with Ella, but the guilt will come in that every time I give her money that that's less money I could've used on my brother and daughter. Then, I will try and solve the conflict by telling myself that I will have a concrete budget on how much per year I can spend on an SD relationship, but then that amount will never be satisfactory too me (it will always seem too low or too high) and it's a constantly moving goal post. I even had an unexpected amount of work earnings this year- enough to sustain an SD relationship for several years, but, even still, it hasn't helped my OCD. Now I just debate on what portion of that if any should go to my SD relationship and what portion should go to my brother and daughter. Ella is very fun to be around and we do a lot of things together that we enjoy like playing backgammon, having interesting conversations, doing stuff outdoors, etc., but it is also anxiety provoking due to my conflict over the financial aspect.

Since Ella lately has been not very available recently, I went on an SD website and met a lady I like a lot from Canada who is also doing a masters in math. We've so far just been communicating through text and facetime, but she is very smart, and I've enjoyed our conversations. I've been thinking of coming to Canada in the Spring to visit her. This is only adding to my OCD for the same reasons.

This conflict has been the biggest cause in my life of wasted hours and dithering. If I could resolve this, I'd have countless hours of extra time freed up where my mind could focus on other things. Paradoxically, I think I actually lose more money in wasting time being conflicted over the relationship vs. family struggle than I do from being in an SD relationship.

Any help here is greatly appreciated. I am hoping to finally move on from this struggle one way or the other. Thank you!

[Sallyskins]

Please, please, reconsider your relationship with this women Ella. And don't get involved with another woman on a similar basis. It amounts to prostitution. If she really likes and cares for you, she won't expect money or payment. Paying for sex - sex on its own or sex with company, as if it were a real relationship - reflects badly on you.

It's a really odd way of thinking about relationships, if you don't mind my saying so. The assumption that you can buy sex, or company, or affection, just doesn't wash. Also, it makes for a power balance inequality in the relationship. Is that really what you think of women - that they are there to be bought? Is it something you'd want for your daughter - to sell herself to a man?

Some men think these are real relationships. They are prepared to pay for the 'girlfriend experience'. But the women are not real girlfriends, and often feel nothing but contempt for their clients.

Kick the SD websites into touch. Go on dating websites where women are going to be interested in you, and not your wallet. Get out onto the dating scene to find a real relationship of equals.

I'm sure it can be difficult, staying with your wife until your daughter has left school, and it does make it difficult to date anyone else. It might be worth your while having a talk with your daughter - either on her own or with your wife - and asking what she wants.

It does appear that you divide your money up into 'duty' and 'fun' - most of us do that to some extent, and most of us rather grudge the money that goes on bills etc! But make sure that you prioritize your daughter (and not just with money) and act fairly by your wife. Enjoy being with your brother - by all means help him out, but remember that being a good brother to him can't be weighed in cash.

Stop measuring things - including other people - according to how much they cost. Most people past the first flush of youth come with baggage - emotional baggage, family, ex-partners, all sorts of things - and most women who want a genuine relationship will accept your baggage, as well as possibly having some of their own.

The OCD is another matter. Focus on doing right by your family and get your values straight. Then perhaps you can tackle the OCD.

[Maximus2019 in reply to Sallyskins]

I appreciate your detailed response, and you make some very good points. I agree that there are more ways to be a good brother than just by helping him financially. Sometimes my OCD causes me to get caught in feeling I have to be forced to help out a certain amount financially to him, though.

Regarding the relationship with Ella, you have some good points there as well. I agree that the financial component can be a problem. However, I am not sure that anyone who is involved in such a relationship means they are lowering themselves (either the man or the woman). It's a complex situation and there could be many reasons why two adults want to have a relationship like this, and the relationship could come in many varieties (with or without intimacy, virtual or in person, etc.). If the people are respectful to one another, and both adults are thinking clearly and making a choice entering into it, I think an argument that it's wrong requires further explanation to validate.

I will, however, reconsider the nature of the relationship with Ella. There was a time when I told her that money could not be a part of this for a while, and she continued to meet me. We've known each other for about 8 years (dated for the last four) so just ending things is not so easy (although I could change the nature of the relationship). One thought I had is just to put all relationships on break for a year so I can focus on family and other goals.

Thanks again for your help.

[Sallyskins in reply to Maximus2019]

There's nothing against helping family out with money, if it is needed and if it's a freely given gift without strings. But mostly families help one another with practical and emotional support - and this is what your brother is likely to need most from you.

It's a myth that women always enter into relationships with men for money or other material gain completely of their own free will. Some may be gold diggers, but many assume that it's an easy way to pay their way to a university degree or support their family. And then they find out different. At the moment, some English universities are allowing escort agencies (better described as 'pimps') to recruit young women, allowing these agencies to have stalls at freshers' week etc. Some girls may be tempted, thinking it's easy money and then find out that it's dangerous and dirty work. Some may find it hard to get out of prostitution once they're in. It occurs to me that this woman in Canada, doing a Master's degree, may be trying to pay for her course that way.

I don't think badly of women who do this - but I do care for their welfare. It's not something they will want to put on their CV, or tell a future partner or children about. I'm afraid I don't think well of men who think it's all right to pay for sex, or that women are a commodity to be bought. Again - is this something you'd want for your daughter?

I also think that you're assuming that this is the only option for you at the moment. I'm sure there are plenty of women who would think it worth working around your current situation to have a relationship with you. If bringing a woman back to your home is difficult, you could go to hers, or go away with her - it appears that you are already doing this with Ella.

Sort out the relationship with Ella - does she have another source of income, like a job? It does sounds as though you're in two minds about her - considering other options while saying you would find it hard to break it off with her. Also, take her feelings into consideration - I get the impression that you haven't done that very much. Ask if she is getting anything out of the relationship with you - and I don't mean money.

Perhaps it would help to concentrate on your family - in particular, your daughter and brother. Keep an open mind about starting a relationship - many a relationship has come about from a chance meeting, or it could be someone you know already.

A relationship should be part of your life - not something you put into a box and use at your convenience. And surely you want to be with someone who genuinely wants to be with you for yourself, not what you pay.

[Maximus2019]

Thanks again for your response. I think there is a big distinction between someone who pays for sex and someone who, as part of a broader relationship, helps pay the other person's expenses (whether it's the man paying the woman or woman paying the man). I think there is validity to your view point. The issue is a big one though with a lot written about it. I have a feeling my issue isn't mainly about the relationship, it's about having a clear mind. I've had OCD about a million things, and now it's just latching onto this. My mental internal dialogue keeps telling me things like have the relationship or don't have it, and I change my mind a million times. This situation is hard to distinguish between the OCD aspects and the practical issues that you raised.

Also, some of the best times I've had in my life were with Ella. I feel that she's enjoyed spending time together as well. She could have been faking it, but it seemed real. To answer your question about my daughter, I can't say that if she were in her 30s like Ella is, and she was in the same kind of relationship with someone like I am in with Ella, that I would be upset about it.

[Sallyskins in reply to Maximus2019]

It sounds as though you could have a good relationship with Ella, but it would need to move away from the business arrangement side of things.

In a close relationship, particularly when people are living together, who pays for what and mine-and-thine do get blurred. But that's not the same as what you refer to as an SD relationship.

I think there are problems with this sugar daddy thing. The name in itself is unhealthy - in a healthy relationship it isn't a parent-child thing, but the union of two equals. And that it's usually an older man paying and a younger woman selling herself says a lot about the power dynamics and the sexual politics.

It does strike me that you haven't said much about your feelings for Ella. Relationships are, of course, about having the 'best times of your life' with someone but they're also about the workaday domestic undramatic stuff and whether you can get along together when the firecrackers aren't going off. I get the impression that you like the fun with Ella but the fact that you keep considering breaking it off with her isn't, I think down to the OCD, though having OCD myself I do know how it affects all that you think and do. I've also noticed that you ask yourself whether you should continue to meet her without considering how she'd feel about it.

I know the part OCD plays in decisions, and that it can interfere with decision-making. But don't put the blame all on the OCD. Relationships are complicated, I'll give you that! Doing the right thing means balancing your own wishes and welfare with your responsibility to others. Try to think about how you feel as well as what you want and remember that there are some things you can't buy.

[Maximus2019]

Thanks this makes sense, and sorry for the late response! I had a great meet with Ella like a month and a half ago and now she's ghosting me again like she's been doing on and off for the last four years.