Advice for Tomboyish Woman Who Has Mainly Dated Other Women?

Wife_and_Mama · 2026-02-09T15:27:12+00:00

Early on, I'd just talk about your dating past and be honest that you're hesitant to share, because you only want monogamy. This will weed out anyone who has a problem with it. If you're dating traditional men, that might be a higher number than you'd like, but best to get it out of the way.
Apologize. Tell him he was right and that you wish you'd handled it better. He might not be interested, but it will at least end your own curiosity and close that door.
Different men have different tastes. It depends on what kind of man you want. Typically, I would suggest a woman with short hair be feminine in dress and style and a woman who dresses "masc" should keep long hair and soft makeup. You have to be true to yourself, though, because ideally you'll meet someone you'll be with forever. It's unfair to bait and switch and unrealistic to plan on wearing a costume forever. Decide how important this is to you.
Your career is wholly independent from whatever relationship cosplay is being pushed on Reddit. The captain/first mate dynamic is, for starters, really better fully embraced in marriage. But in dating, it's more about things like where to eat and whose car to take to the football game. In marriage, it's more about who gets the final say at an impasse. Even then, the reality of how that works in marriages greatly varies.
I would talk openly about issues, not who is leading. You have to train yourself to hand over the reigns. That's not really work he can do. If he shows initiative, reward, don't criticize. Early in a relationship, that could mean accepting his dinner and date choice, because he made it and you didn't have to, even if you're not really feeling like Chinese. In a marriage, it means stuff like keeping your mouth shut when he sucks at loading the dishwasher, because women who criticize get to load their own dishwasher.

Jenneapolis · 2026-02-09T15:55:17+00:00

Let's start off with - do you want a male led relationship and if so, why? Despite what you see here, you don't have to be ultra feminine looking to do it, it's not a requirement. But I am curious as to what you want out of a relationship in terms of leadership.

RedPillDad · 2026-02-10T03:33:50+00:00

How does a somewhat masc / tomboyish presentation impact SMV?

SMV for a woman is heavily skewed to physical beauty (hotness factor) because men are wired to respond to that. If you want more than hookups, pay more attention to RMV. This is a great forum to explore that.

Amping up the sex appeal can derail RMV. Fun gals can find themselves slotted into the Fckzone, never taken seriously. Especially true if they chase Chads. Being here means you're already trying to do better.

Tomboy versus feminine is a different metric than hotness. Sexual polarity has wide variance beyond masculine male, feminine female, as does attraction. Some strong males are attracted to delicate, feminine women and some are attracted to their female equivalent.

My suggestion would be to explore your feminine side while keeping that warrior spirit. You don't have to be locked into one predictable archetype.

Captain & First Mate means you both contribute, both capable of leadership and initiative. It's not a lopsided power dynamic. OP, you sound very capable of this.

teufelinderflasche · 2026-02-10T07:26:00+00:00

As a man, I would say most men would not have an issue with your experiences with women.

TheBunk_TB · 2026-02-09T22:36:23+00:00

Have you reached out to him?
Don't be combative and "nut check" him.

CountTheBees · 2026-02-10T00:13:18+00:00

Simply saying you are looking for an exclusive monogamous relationship will set the tone. I think there are a lot of men who want to "just have fun" and not get locked down to anything but you want to steer clear of those men anyway. If he doesn't have feelings early on he's not your guy.
Answered by others.
It impacts it a lot, by up to 28%! And men mostly prefer longer hair on women. But also your current style may help you vet for men that will be okay with your past and your journey. That might be enough of a reason for you not to care about the hit to SMV. Or maybe you will retain some masculine elements in your style but incorporate more feminine ones as well as your hormones change and you feel different, it is entirely up to you.
He has to earn your trust and respect first. Working for him/finances/etc is very much a marriage/committed LTR thing. By that point hopefully he will have resolved your qualms and you feel like he has made good decisions worthy of trust and commitment.
Not sure what the question here is. But most men are somewhat resistant to talking too much about their feelings or anyone else's. They will try to physically solve your problems rather than soothe your feelings.

AutoModerator · 2026-02-09T05:12:08+00:00

Title: Advice for Tomboyish Woman Who Has Mainly Dated Other Women?

Author AnimePleistocene

Full text: Hi, hope it's cool to ask a few questions!

Bit of background on me: as a little kid (pre-puberty), I was fairly tomboyish and liked to build model tanks and planes. Starting in my teen years, I felt awkward engaging in performative femininity and presented in a masc way. I was more attracted to women than to men and ID'd as lesbian.

In my early 20s, I learned that I had a hormone imbalance and started treating it. After I did that, my attraction to women faded and my attraction to men greatly increased. This was not an instant process. It happened over a period of months. It isn't a common experience, but it sometimes happens.

I would deeply appreciate help with these issues:

When should I tell men about my previous preferences / sexual history? I don't want men to think that I'm interested in threesomes, being someone's bi third wheel, etc.
I have dated one man (we met last year) and I found him attractive, intelligent, and easy to respect. However, I got defensive about certain things and we had a blow up over something he said on Reddit. In hindsight, I can see his perspective & I wish I'd handled it differently. I'd like to date him again, but I have no idea how to let him know its okay to pursue me. Any ideas on how to do that? I'd like to at least explore the possibility of dating him again.
How does a somewhat masc / tomboyish presentation impact SMV? I'm trying to wear brighter colors, but I still tend to wear jeans + jacket + have a pixie cut. It'd be fair to say that I look a bit like this: https://www.newamericanjackets.com/wp-content/uploads/2019/11/2019-Action-Movie-Charlies-Angels-Kristen-Stewart-Jacket-600x800.jpg
If the man is the Captain and I'm his First Mate, does that mean I assist him in any task assigned to me? Like if he says he wants help with his business should I go to work for him?
In my two LTRs (both with women) I was expected to be the de facto leader and simultenously be as emotionally supportive and empathic as a female friend. This was extremely difficult. How, in a relationship with a man, do you let him be the leader? Do you talk openly about this stuff?

I hope this makes sense & appreciate any thoughts!

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2026-02-13T13:23:56+00:00

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MovingForward2Begin · 2026-02-15T02:55:38+00:00

I would suggest working on the femininity. On average, men want feminine women. It is what it is like it or not. It sounds to me you have always rejected your femininity, why not try embracing it for a change instead?

Some men will care about your sexual past. I know I would. Some guy said guys wouldn’t care, but he is wrong. Do I want to have to worry about my wife being around women? Not really.

I would tell men you had those relationships because it was a confusing time for you and made bad choices, which would be the truth. Let them know that it is no longer your life and you repent of those mistakes. Again embrace your femininity so your man is not left wondering.

Title	Advice for Tomboyish Woman Who Has Mainly Dated Other Women?
Author	AnimePleistocene
Upvotes	13
Comments	23
Date	February 9, 2026 5:12 AM UTC (5 months ago)
Subreddit	Posted in /r/RedPillWomen
Original Link	https://old.reddit.com/r/RedPillWomen/comments/1qzvghq/advice_for_tomboyish_woman_who_has_mainly_dated/
Archive Link	https://theredarchive.com/r/RedPillWomen/advice-for-tomboyish-woman-who-has-mainly-dated.1573065 https://theredarchive.com/post/1573065

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