His Take: “How Do I Put the Moves on a Woman?”

I am a happy, well-adjusted bisexual woman in my mid-twenties. Since I began dating in my early teens, I’ve been in a mostly steady stream of long-term, monogamous relationships with men. I’ve always been attracted to women too, but my experience with the fairer sex is limited to a few random (mostly drunken) sexual encounters — no actual dating. My amazing boyfriend of three years told me early on that he would not consider it cheating if I wanted to see women too. I recently decided to take him up on that, and with his blessing, I set up an account on a dating website. Overall, this has been a good experience. I’ve even developed a great connection with a beautiful girl I’ll call “Sarah,” who is also new to dating women. We’ve been on several great dates and exchanges lots of flirty texts and emails. I know she is in to me. However, we’ve only kissed a few times, and I think we would both like to take things further, but neither of us is quite sure how. As a pretty girl, I’ve never had to make the first move before. The man has always taken the lead (at least in the beginning of a relationship). Best I can tell, the same is true for “Sarah.”

So here’s my question for you guys: how the hell do you do it?! I’m not asking for step-by-step instructions for seducing a lady (I’ve got a pretty good idea what I’m doing, thanks!), but I would love some advice on how to get over this weird shyness and just take the plunge. This is something most guys figure out how to do in high school, and here I am, an adult, too intimidated to lean in for a kiss until she’s walked me to my car! Any tips to help me unleash my inner Casanova? — The Tension is Killing Me!

MATT: Let me get this straight (pun intended), you spent 300 words talking about the understanding boyfriend, the drunken experimentation, and going online to source out some lady bits; you carefully note that you’re already versed in seduction (hilarious detail) then—drum roll, please— you finally get around to asking your big question: how to get over this “weird shyness”?

Let’s skip the self-esteem, sexual identity, open communication (with “Sarah”), fidelity chat we could have and instead address what you’re really asking for: Permission. Permission to get down and dirty with your gal pal? GRANTED. Permission to, quite possibly, not be very “good” at it? GRANTED. Permission to totally dig it? GRANTED, baby. If you’re certain she’s down for some lady fun, find a time and place that’s mutually comfy and safe, take off your pants and go exploring…You’ve come this far, right?

So? Actual tips? Okay, fine: Take plenty of lotion along on your all-girl picnic, hand-warmers (essential), an open mind, a squeaky-clean body (without a ton of perfume, thanks), a list of questions, lots of time, some candles, and a sense of humor. Go ahead and bring Sade for the soundtrack; she works for almost any occasion. Oh! And don’t be afraid to go basic: “Truth or Dare” and “I never” are both excellent games, if you ask me.

JAREK:In high school, we all had raging boners 18 hours of any day, so we *had* to do something. As such, we just went for it. We got shot down a lot, but sometimes we didn’t. It only takes riding a bike so many times before you no longer worry about falling off. That’s the hump you need to get over. The biggest fear in making a move is thinking that the other person is “better” at this stuff than you and that you are going to end up looking like an inexperienced idiot. You both appear to have the same experience with this sort of thing, so she is likely just as nervous as you are.

Knowing that, the most important thing is for you both to feel comfortable in your situation. Go back to the basics of feeling comfortable when you’re exploring intimacy – lights on or lights off, bed room or living room, music or TV in the background. Have a drink while you two get comfortable in front of each other, just take the edge off. It’s not called liquid courage for nothing. Once you’re there, communicate. “Is this okay?” “Do you want to keep going?” If you’re engaging yourself with the other person, she isn’t going to feel rushed or violated or uncomfortable, and neither will you. You can progressively move your way up to exploring new things, and you’ll be doing it together.

JMagic: I’m going to let you in on a little secret: guys never figure “it” out. If by chance some guy did there’d be this mythical 10-page-or-less book containing that info that would sell out all over the place and the only way to get your hands on it would be to take out a second mortgage and know some secret handshake … maybe I just haven’t learned the handshake yet.

But seriously, every guy, including your current boyfriend reaches a stage in the relationship where he wants to take it further but the awkward nervousness and fear of rejection make it difficult to do so. Now, the ‘Casanovas’ of the world have just learned to better contain said awkwardness and use it to their advantage. Others simply fumble their way around and find out, or are still searching many years after high school.

The best way to do it is … to do it. Plain and simple. Part of the joy of a new relationship is being in the exact same spot you’re in right now. You can both feel it. You know you want it. But the so-called rational part of you wants you to keep waiting until the obvious ‘open for business’ sign turns on. Not gonna happen. Especially since you haven’t been in this spot before. So, tastefully, dive right in and make your move. Sure, you might get rejected, but who cares? From the way you describe your relationship with your boyfriend and woman you’re dating… you’re having your cake and eating it too. Enjoy it and try not to put too much thought into it.

DENNIS: Short of directing you to the world of pick-up artists, my suggestion entails two basic components: 1) body language and 2) baby steps. Pay attention to how she responds when you’re being intimate. Is she pulling away? (Bad sign.) Is she leaning in? (Good sign.) Combine that with what I call baby steps: Don’t stick your hand straight down her pants right away. Instead, move your hands over her body and see how she responds. Start with the “safe areas”… hands, arms, upper back, you know, places you’d naturally have your hands as you’re kissing her. Then, move them to slightly more risque areas… her hips, legs, small of her back, neck. Again, notice how she responds. If she moves toward you, or even reciprocates, then keep progressing. If not, slow down, hot shot. Once you feel that she’s sufficiently comfortable with you touching her (believe me, you’ll know), then you can move on to the, ahem, private parts.

And wow, that just got really graphic, didn’t it? I think I’ll let you finish the seduction from here, mostly so I can go take a cold shower now.

* If you’d like to ask the guys a question, simply email me at wendy@dearwendy.com with “His Take” in the subject line and I’ll pass your question along to them.


  1. Love Matt’s answer!

    1. absurdfiction says:

      I think Matt’s answer was unnecessarily condescending. The LW is asking for TIPS on how to overcome shyness in a new romance, and he gives her “permission” to do so? Who the hell is he to give her permission anyway? And the snarky comments about sexual identity, fidelity and lotion were kinda off the mark too. The other guys actually answered her question, he just made a long, vaguely offensive joke of it.

      1. I felt like she was a bit rude… “(I’ve got a pretty good idea what I’m doing, thanks!) Oookk then?! Eh.. either way I just wish the LW luck.

      2. I agree with absurdfiction, he doesn’t seem to get it. She already has permission to move forward in her relationship with the one person who matters, her boyfriend, she doesn’t need his. She wasn’t asking for permission, she was asking for some tips on how to initiate a sexual relationship not fueled by alcohol and hormones. She’s actually dating this girl, not randomly hooking up with her, there’s a difference.

      3. absurdfiction says:

        Exactly, cmarie!

      4. WatersEdge says:

        Agreed. Either he didn’t understand the question (which WAS- how to make the first move, which was NOT- how to initiate “an all-girl picnic”). He actually sounded offended by the question, which I honestly don’t get. Way off the mark, Matt.

      5. BoomChakaLaka says:

        That’s not what I got from Matt’s answer. I thought Matt’s answer was addressing the fact that she knew she wanted to do this, but maybe she needed a push. There could definitely be an aspect of guilt in this that we might be overlooking.

      6. I don’t read any guilt in her words. She’s not asking if it’s right, or if it will change her relationship with her BF. If she hadn’t even mentioned her BF it would never occur to anyone that she would be feeling guilt. It reads, to me, that she’s just starting to explore a more emotional relationship with a woman and wasn’t sure how to get past the awkwardness she never felt in her past, drunken hookups. Being sexual in a real relationship, with someone you actually car about, is different than just “hooking up” and it’s reasonable that she would be nervous. It’s her first foray into dating as well as Sarah’s and anyone who has felt nervous about getting physical in a new relationship would understand that.

  2. I really like all of these answers, and all for different reasons.

    Maybe we could have a “Queer Questions” section, like “His Take”? Queer women are about the only answer segment that you don’t already have, Wendy (since you are straight and the guys here are straight and gay), and it would be a perspective that I, the LW, and others would surely appreciate. (BTW, here I’m just using queer as shorthand for LBTQQIA, since the acronyms can become unwieldly.) Anyway, those are my two cents, and I do actually like the guys’ answers, too. (And yours of course, Wendy!)

    1. fallonthecity says:

      I think that’s a good idea!

  3. “raging boners 18 hours of any day”

    Not a bad mental image

  4. Great answer from Dennis!

    1. fast eddie says:

      The big risk when you start touching those special body parts is that she’ll start squirming to the other end of the couch, grab her purse and jog to the door, never to answer your phone calls again. There’s no way to avoid this gamble. I had some success with offering to give a massage which often resulted in her arousal.

  5. you’ve got to be kidding me. we’ve talked about situations like this before on dear wendy. just because the plumbing is different, doesn’t mean it’s not cheating. your boyfriend may be “alright” with this, but fact of the matter is, you’re cheating on him. i don’t expect your relationship to last. be in love with a man or be in love with a woman. but pick one. i’m sick of people saying they’re bisexual and using that as an excuse to have double the relationships.

    1. BoomChakaLaka says:

      Whoa, whoa, whoa, rock. Calm down with the disrespet. Different strokes for different folks. There are relationships where both parties can agree to see other people. It’s called Open Relationships. Anyway, the LW didn’t ask about whether or not her bf was comfortable with it, she asked how to seduce a woman. Stick to the question at hand, and stop judging.

      1. kerrycontrary says:

        I agree with boomchakalaka (your pseudonym makes me giggle). If they are in an open relationship then that’s their business! If she was sneaking around then yes I would consider it cheating, but the guy says he’s fine with it so why don’t we believe him?

      2. Totally! If LW’s boyfriend really isn’t o.k. with it or hasn’t thought it through, well, that’s HIS problem, not hers. She’s been totally upfront about it, and as far as we know she hasn’t promised him any threeways and he even helped her create a dating profile! If for some reason he later on decides it is cheating, then they’ll have to revisit it, but you can’t place the blame on her. She’s made her needs known and he’s given her permission to explore them.

    2. Wow! Really? Not everyone is in a closed minded relationship! Her boyfriend is ok with it, and this is something that is becoming widely popular and accepted. Layoff this LW. She is asking for advice, not to be critized by some close minded, attitude having, mean spirited person who sounds like they are just upset with her sexual orientation.

      1. I kind of agree with rock…it is like asking for tips on how to cheat on your boyfriend, even though I guess its not technically cheating since he says it’s okay.

        But you have to wonder…would he be equally okay with it if she wanted to pursue a relationship with another man? And if not, what is different with her pursuing women?

        Ultimately, IMO, if she feels the need to be out dating other people, male OR female, this relationship is not destined to last.

      2. Wow Emjay, I normally really like your comments but this one feels so condescending towards people who are in committed exclusive relationships.

        “Not everyone is in a closed minded relationship!” –
        I am not a closed minded person or in a closed minded relationship because I expect my bf to be faithful. I completely agree to each their own and that if this couple is open that is fine, but don’t disrespect my relationship style!

      3. I think emjay was speaking more towards a close-minded attitude, not generalizing that all monogamous relationships are close-minded. At least that was the way I took it…

      4. cmarie you are correct. I am in an exclusive relationship as well. I am not bashing the exclusive people by any means. But if you read rock’s comment I was talking more along the lines of how I percieved rocks comment. It is by no means bashing anyone’s relationship what-so-ever. So i do apoligize to the people who have misunderstood my comment, and I could have probably worded said comment better.

      5. Hana read my reply to cmaries comment and i hope i clarified. Like I said (and many people on this site know I use my personal experiences ALOT in my comments) I apoligize if you mistook what I said but, I too am in an eclusive commited relationship, and we are both faithful. I should have worded better.

      6. its ok. I have worded things poorly on this site too and took a lot of heat for it. And like I said, I normally love your comments. 🙂

        I agree with what you were trying to say too… Now if only I could undo my thumbs down lol. I would change it after the explanation!

      7. I just re-read your original comment and I totally misread it too, so disregard my comment, too. It’s weird how wording can get so misinterpreted, sorry about that, and thanks for the clarification!

      8. I agree with most of your comment, but closed relationship ≠ closed minded.

      9. For clarity- that is a not-equals sign, as in, closed (monogamous) relationship does NOT necessarily mean closed-minded people are in it… if you disagree then you have either been exposed to some pretty lame monogamous people, or you are ironically closed-minded yourself.

      10. yikes. excuse me for having an opinion, but i refuse to let you get away with posting that the reason i made this comment is because i’m mean spirited and upset with my sexual orientation. sounds like you’re being a bitch just to be a bitch. that comment came from nowhere.

        fact is: like amber (below) said. i wonder how “open” the relationship would be if she wanted to date other guys, instead of dating women as well as her bf.
        the situation sounds like the bf is just a jerk who 1. doesn’t really love her enough to care whether or not she dates other people, or 2. is a perv who thinks he’s going to get a threesome out of this.

    3. JennyTalia says:

      I actually kind of agree with the cheating part. That’s the first thing I thought when I read the e-mail – that the boyfriend may not take her bisexuality seriously since he is so ok with her seeing women outside of their relationship. He may not realize that bisexuality includes actual emotion and it’s not just a Girls Gone Wild romp. But that’s just my unsolicited third party opinion, different strokes for different folks.

      1. ” He may not realize that bisexuality includes actual emotion ”

        exactly. He likely does not realize that his girlfriend may develop actual feelings and intimacy for this other person.

        Or, he’s hoping it will lead to a threesome.

      2. I had the exact thought as you, that he probably doesn’t take it seriously/didn’t think she would go for it/doesn’t understand it/thinks it will lead to a threesome.

        It’s great for him if he totally gets it and really is ok with it and I strongly hope thats the case. Hey, maybe he is bi too and gets a little man-love on the side as well. Or maybe he can bring another girl home if he wants. If that works for them, fantastic! Just don’t want him to be disrespecting his gf or the girls she brings home.

      3. Jess of CityGirlsWorld.com says:

        Agree, maybe it’s because I’m a prude or maybe it’s because the thought of sharing/exploring outside my OWN relationship gives me heart palpitations.

        I have curiosities too but there are other ways to explore them. Even a fling or an experimentation of sorts is different than “dating” another person. LW isn’t (just) exploring a sexual desire. She says herself that she wants to “see women too.” To further that goal, she’s met someone online, gone on dates, and developed a relationship that is about to become physical.

        I know, I know, that open relationships work for some people and I (try to) respect that. It’s just hard for me to make that leap to believe that a couple making this choice for the first time after being monogamous for three years (with presumably well-established patterns and expectations) are really prepared for the huge transition and emotional whirlwind this is likely to be.

    4. absurdfiction says:

      If everyone involved is happy with the situation, what’s the problem?

    5. The plumbing being different has nothing to do with whether its cheating or not.

      Pretend the LW started by saying “I’m a happy, well adjusted straight woman in my mid-thirties” and then proceeded to describe a situation in which her boyfriend was okay with her dating another man… If he knows about it, and is alright with it, it IS NOT CHEATING. Adults everywhere choose to be in relationships in terms that they define. An open relationship may not be for you, but for some it is exactly what they want and need.

      It is completely natural to be attracted to people other than your SO. For some, a relationship can only work with complete and total monogamy. They choose to be exclusive and are happy ans satisfied as such. For others, acting on other attractions is completely natural, acceptable behavior. It is CHEATING when it is done by one partner without the knowledge or blessing of the other. The deception is what makes it cheating.

      Bisexuality just adds another level of complexity to the situation. But this is a discussion on making the first move, so I’ll stop here.

      1. That’s true – it’s only cheating if it is done without the knowledge and blessing of the SO. On the other hand, knowledge by itself can’t be taken as a blessing.

        There are many relationships where one partner will disclose their intentions to see other people. Should the SO end the relationship if he/she isn’t ok with it? Of course. Does this always happen? Of course not. Emotional logic and rational logic can be contradictory – especially when it comes to sex and relationships.

        For the person looking to date outside of the relationship, there is at least some ethical responsibility to look out for your partner’s emotional and mental well-being and/or end the relationship if appropriate (regardless of what the SO says they want).

        Nonetheless, since there is no way we can know circumstances of the LW, it doesn’t really matter.

    6. I re-read the letter. It does seem like the LW is trying to have a relationship with Sarah – one-on-one dates, without her boyfriend. Sarah is into the LW…

      I picked this one from Dan Savage – make sure that Sarah knows you are in a stable relationship with your boyfriend, and you will not leave him for her. If she’s into you emotionally, don’t lead her on. For your own sake, I hope you won’t fall for her, because that would most likely be the end of the relationship with your boyfriend.

      IMHO, emotional cheating is just as bad as physical cheating. Maybe even worse, since you’re slowly pulling away from your SO, as you get your emotional needs filled somewhere else.

      1. SpyGlassez says:


        I had the same reaction when I read the original letter: does Sarah KNOW that the LW is in a relationship? If not, she will probably feel betrayed when she finds out, especially if she thinks THIS is a monogamous relationship. Best to be open from the beginning with both of them, and be sure the boyfriend knows this isn’t just hooking up for some side action; as others have said, he might see this as just a physical action on your part and not understand the emotional ramifications of you being in two simultaneous relationships.

  6. BoomChakaLaka says:

    Great answers. This is an interesting one for His Take. I would have definitely put this on a Your Turn and take it from there. I don’t know how to seduce women, but I certainly know how I like it. Matt and Dennis pretty much have it about right.

  7. LolaBeans says:

    “Part of the joy of a new relationship is being in the exact same spot you’re in right now. You can both feel it. You know you want it.”..
    I loved that line from Jmagic. so true.

  8. Just relax and let what happens happen. She is just as nervous as you (same with a relationship with a man, and the begining stages before the sex starts), take your time and things will progress naturally. If you are in a hurry, I 100% agree with Dennis. Try out things that are not so “in your face” so to speak. And then see how it progresses. It might not happen the same day, but you will be letting her know you are ready to take that next step. 🙂 Good Luck LW!

  9. Skyblossom says:

    I think they all hit it but I especially like the advice from Dennis to take it slow and see how she responds. That’s great advice for anyone in a dating situation.

  10. This may be TMI, but I wouldn’t see how it’d be any different than “putting the moves” on a dude. I will say I haven’t had any lady experience. I mean, I AM a lady. And the way I enjoy being seduced is a nice dinner, candles, music (soft but not that corny stuff, something different and calm – do NOT put on some Norah Jones because that screams “hop in bed” at least to me!).

    Then you let the evening progress. I know it’s awkward at first, I think it is anytime with someone you like, but if you’re in the comfort of your own home, you can sit down, touch her (not creepily), and kiss her. If she’s digging it, kissing usually leads to making out, leads to other things. Generally if you listen to someone’s body language it’ll tell you if what you’re doing is reciprocated or if it’s time to tone it down.

    Good luck!

  11. Just relax and be natural. Being intimate with a woman is different than being with a guy on many levels but emotionally it holds the same level of shyness and potential for awkwardness. Set the mood but don’t force it. Find out little things that she likes that could initiate a safe intimacy. I love it when my partner touches my back, it’s safe but relaxing and it feels intimate because it’s skin-on-skin contact. It’s all about reading the signals but also being comfortable with yourself. If it feels disgenuine to you, it feels disgenuine to her so make sure you’re okay with what happening too. And don’t rush it, if there’s a connection it will happen eventually; there is no set timeframe.

    1. cmarie, can we be friends in real life? I feel like all of the lady-lovers in my own life are crazy, and sometimes I wish I had a sane fellow lady-lover to talk to/ask questions of.

      1. Sure! At least you have fellow lady-lovers. Where I’m from they are few and far-between. Yay for new friends!
        p.s. I love your icon, he just looks so gwumpy; it’s cute. *insert baby-talk*

      2. Haha, can’t say I’m a fan of baby talk, but I’m glad you like my icon. Email me at christyfromdw@gmail.com and I’ll respond from my real email so you have my contact information 🙂

  12. I personally like Dennis’ answer. Simple, to the point and clear. Girl needs to get over her fears and just TRY something.

    I think, perhaps, that LW needs to start making small moves sooner – is she reaching out and touching her hand across the table at dinner? Brushing a stray hair away from her shoulder? If you start with the really small things, it makes the big things easier – especially with all that sexual tension of it being your first time.

  13. I little off topic, but Matt looks EXACTLY like a guy I dated once who was also named MATT. Sounds like him too…..but it isn’t him….I think……

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