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TherapistJen, LCSW, CPC
Category: Relationship
Satisfied Customers: 3491
Experience:  Licensed Clinical Social Worker
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I am 48. Ive been dating someone, Rick, for about 5 months

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I am 48. I've been dating someone, Rick, for about 5 months now. He is 48, 4 months younger. Shortly after beginning to date he wanted to open a joint checking account, to build trust. I agreed and opened it with $300. 2 weeks after that his contract job ended. I began to put money into the account to help him out a little. His unemployment ran out. I began to put more into the account. He says he loves me and wants to move into together in September and get married. I have reciprocated the feeling, but am beginning to wonder. He has some OCD tendencies and tends to over worry about things, becoming very moody at times. We have had virtually no intimacy for the past 3+ months, which I'm trying to be understanding about, but bothers me as I feel like I am unwanted, although he tells me that is not the case. He is really sweet though, calls me several times a day, loves animals, and alot of the same music I do.

Someone I was seeing before him, Bill, contacted me and asked to see me. He is 54. I explained that I have a boyfriend, but I finally decided to see him anyway, as my sister says you need to be sure before you marry the other guy, if that is what you really want. The 54 year old (yo) owns his own home, his own company and is very smart. He is also very passionate.

My question is: Can I date Bill while dating Rick? Bill knows about Rick, but Rick does not know about Bill. I don't want to end it with Rick as he may improve and be the person I want to marry. I would like to date Bill because I'd like to get to know him better to determine if he is really what I want. I don't want to hurt Rick by dating someone behind his back. I already feel so guilty about the one encounter with Bill and a few texts I've sent Bill. However, Rick gives me no affection, and is just plain depressing me. But I care about him and want him to be happy, but I want to be happy too. Please give me your opinion. I don't know what to do. I would not want anyone to cheat on me though, but I have always thought of the other person in a relationship and have ended up paying the price for it in the end, so I'm leaning towards putting my own best interests first.
Submitted: 5 years ago.
Category: Relationship
Expert:  TherapistJen replied 5 years ago.
Hi. Welcome. I am a Licensed Master Social Worker with more than 20 years experience working with individuals and families on a variety of issues.

I am so happy you have reached out here and I commend your openness and honesty.
I hear that you are not very satisfied with Rick and that is are entitled to those feelings. There are some issues that could be getting in the way of the deeper connection. His financial issues, relying on your for money, ocd tendencies and lack of intimacy. This can lead one to feeling disconnected and I understand your predicament.

Now along comes Bill, established, secure and someone that you might want to re-connect with. Nothing wrong with that whatsoever and I also like how you are desirous of looking out for yourself especially since you have given over to others needs and desires in the past. I also hear you when you say you feel guilty and wouldn't want anyone to cheat on you and you will give that same courtesy to Rick.

So, I am with you in leaning toward putting your needs in the foreground here and spending some time with Bill. But, I do not believe you will be able to do that with a clear head or heart until you talk to Rick about your feelings in the relationship and your desire to date another person or other persons. I truly believe that once you do that you will feel the freedom to do what feels right for you and re-connect with Bill. From what I can tell about you, if you don't talk to Rick in advance then you won't truly feel free and you will feel that you are being hurtful to him and I don't think you want that.

So to simplify...yes go out and spend some time with Bill. Have a conversation with rick first and let him know of your feelings and desires. He most likely will not be happy about it, but that doesn't mean you aren't entitled to explore this other option.

How does that sound?
Customer: replied 5 years ago.

Rick is so vulnerable right now there is no way I could tell him without losing him and he would never trust me again.


So I'll just concentrate solely on Rick and if it doesn't work out with him, see if Bill is still around, after all, it has been 5 months since I talked to Bill before last Monday anyway.


I really think Bill is the better choice for me, on an intellectual and attraction level, but I don't know that he has any long term potential for me and can't figure that out without dating him. He did say he thought he could get serious with me if he spent more time with me.



Expert:  TherapistJen replied 5 years ago.
And I am not wanting anyone to feel hurt in this situation but I should point out that once again you are putting your needs away in the face of someone elses...makes you very loving but some self love would be good too.

I will support you in whatever way you are leaning in this. We are all vulnerable and that never changes. Let me know your thoughts.
Customer: replied 5 years ago.

I know my kids aren't happy with Rick, they say he is weird. My son has had an altercation with him resulting in a charge for Rick that he is on probation for until July.


Perhaps I could see Bill a few times without telling Rick, just to see if there is anything there. Maybe keep the physical stuff out of any time I spend with Bill so I can see if there is anything there other than physical attraction between us, then I would feel way less guilt. The plan was just to talk to Bill on Monday, but first thing he grabbed me and gave me this passionate kiss you would not believe...


What do you think?

Expert:  TherapistJen replied 5 years ago.
You made me laugh with the passionate kiss and I would not believe...I do you? You are currently living without intimacy and you are attracted to Bill.

I don't love to hear that news about Rick and an altercation with your son.

I will support you in whichever way you go...if you want to dip your toe in the water with Bill and keep that quiet then proceed in that sounds to me like you need to play this out and see what the feelings are. So, I am here anytime you need.
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