When I asked him if we could please do that next year, he got really hurt and didn’t even want to look at me or face me. He said he was sad he disappointed me, but then I got even more upset because I just wanted to let it go and go to bed. He kept saying he wanted everything to be perfect, which still confuses me. The whole night was honestly like he went on autopilot as he did the same exact stuff he does every year with his parents and just wanted to include me without checking if I even liked any of it. It wasn’t bad, but it was still lackluster and impersonal.
I think in the future if I want something like this, I just need to plan stuff. Is that too insulting? If not, how can I get him to understand going on autopilot isn’t going to work for me? — OverAutopilot
It doesn’t help that you’re sending mixed messages. On one hand, you told your boyfriend that it’s doesn’t really matter what you do for NYE as long as you’re together and as long as you kiss at midnight, and then, on the other hand, you’re upset that the evening was lackluster and impersonal. I mean, sure, you can fault him for not listening to you about the second point — although could you not just kiss him? Was he not with you at midnight? I don’t really get it — but he did meet your first criteria which was to spend time together. YOU were the one who told him that was one of only two things that mattered. If you wanted something special, you should have expressed that. You should have actively helped plan a special night. Honestly, if you’re taking a passive role in this relationship and letting him do the planning for things that are important to you, it doesn’t sound like he’s the only one who’s “going on autopilot.”
If you want him to understand that autopilot doesn’t work for you, start with the words you say (“I want something special”) and continue with the actions you take (help plan something special).
Yeah, you should not. Aim higher than some kid who wants you to give him oral sex in a car or behind a shrub or in the break room or wherever he has in mind three times a week. You’re a 50-year-old woman; it’s time to cultivate some self-respect. The draw of a much younger man is kind of defeated when the best thing he can promise you is that the sex will be quick!
And if a hotel is your preference, I’m assuming at least one of you is in a relationship (you?) and the other (him?) is either also in a relationship or lives with Mom and Dad. If I’m right, and you’re in a relationship, and it’s not an open relationship, make a New Year’s resolution right now to fix your relationship or get out instead of cheating with someone half your (or any age, really).
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.