Dating an Older Man: Or, The Faceless Randoms of Bygone Eras

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Hi Suggestive, I think I need some reassurance in my relationship (I’m female, 23 and he’s male, 46. We’ve been together for about 5 months). This is my first relationship ever and my partner has definitely more experience than I do. The part about his past that makes me feel the most insecure is knowing/hearing/imagining all the past sexual experience he has had. He’s always told me that I’m the first one he’s been in love with and with me he has the love and the sex. It’s been hard to get that in my mind automatically because I grew up with and internalized a lot of sex negativity and thoughts related to that. I know he loves me and this relationship is far different than anything he’s had before. But my mind constantly runs with the thoughts of him and faceless randoms doing it. I wish I could rewire my mind and not feel this way but it’s so deeply ingrained in me! How do I begin to unlearn this and have it stick?

I might suggest that the frustration is not necessarily about the people he’s had sex with, but the fact that he simply has more experience than you do. That may be a problem that continues to regenerate over and over again within your relationship. Has he felt this before? Has he done this before?

 When dating with a large age discrepancy it can be a real downer if everything new and exciting is something your partner has already been there, done that. Of course, this depends entirely on your partners attitude about the situation. Some people have a joie de vivre that makes every situation feel thrilling and new. They are able to experience high levels of joy over and over again. Others wallow in a sense of I’ve already done this and waft disinterest to their parters. These are horrible people and you should avoid them at all costs. Just kidding. Mostly. Not really.

If we’re talking about sex, I wonder what his attitude towards your sexual relationship is. He assures you that he has the love and the sex, but do you feel that from him, too? (

I feel as though your brain is giving you a warning. If you are uncomfortable with something, listen to that discomfort. Do not try to rewire your brain. Why do you feel uncomfortable? What is your discomfort telling you to do? If it’s saying “I cannot completely be okay with this, even though I do not know why” that is a perfectly okay thing to feel. Sex positivity does not mean, and will never mean that you have to be okay with everything related to sexuality. It certainly does not mean you have to listen to your current significant other talk about previous relationships, what they did, who they were, etc.

There are some exciting things about dating an older man. He has some experience with what he likes and what he doesn’t like. But every person is different. He’ll be able to show you some things, but you’ll be able to show him some things too. Even if this is your first relationship – which – I think – we should take a second to talk about. This is your first relationship. I’m assuming you mean your first sexual relationship, but it could be your first romantic relationship as well. That’s a huge big fucking deal and frankly I’m not entirely sure that dating someone so far ahead of you in terms of experience is the best idea. I’m not saying it’s a bad idea or that it’s an impossible idea, but I think it presents several unique problems of its own.

Everyone enters into relationships in different places with different experience. This is how it’s always going to be in any relationship you’re in. But the first relationship you’re in helps you set the stage for the next relationship you’re in, and the second relationship you’re in helps set the stage for the one after that. Each relationship teaches you something new about what you want and what you don’t want. I worry that dating someone with so much experience may sway this process into his favor.

Remember that a relationship can and should be what makes you happy, what feels comfortable, what you want it to be. Someone who has been around the block a few times doesn’t get to choose what it looks and sounds like. Is this partner someone who you can explore different aspects of sex and love with openly and honestly? If so, revert back to question one : what does your discomfort tell you? If not, don’t look for any more reasons to stay with him.

Your question included not one line about what you want in your relationship together. Take a step back and think about that openly and honestly and alone and see where it takes you.

Best of luck!

Do you have a question about sex or love? Submit at http://www.suggestivetongue.com/ask and I’ll answer it on my blog!

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