Dating And Heeling, When Do You Mention It?

[HighHeelLover86]

I've been thinking about this on and off for years and thought it would be a neat idea to ask various opinions on the matter, so here goes. Lets say you are single and looking to find a date. Lets also add that you don't have the intent of a one night stand or short-term fling in mind, or in other words, you are seeking a relationship. Finally lets add that you are doing internet dating or some such thing that would mean your initial contact with said potential date would not be in person. At what point would you mention/discuss your heeling habits?

Not being that thrilled about going out to find new potential mates, I date online frequently or use personals. I never directly mention my love of heels in my profile but I often make sly references to it, such as using a screen name like "HHLover". I also feel that since my goal is a serious relationship, and possibly my life partner, that I should mention my passion sooner rather than later, even though I know it has cost me some dates before. Just so you can get a better bearing on the question I personally am straight but the question applies to any orientation.

I look forward to your feedback.

[Stilletto2004]

The first time I met my wife I was wearing shorts with pantyhose. I really never had to break it to her that I wore hosiery. From there the discussion went to 'what else do you wear' Heels and skirts, that's it! I told her of my prior life as Jennifer, but how I really didn't like fake boobs, wigs, and makeup all that much. Just the clothes. Call me a waist down crossdresser I suppose. But the thing is, I don't consider it crossdressing, I consider it my option to wear what I want. I never want to present as a female. I don't wear heels to feel feminine, I wear them because I think they're cool. Just like I think my truck is cool.

[HighHeelLover86]

Thanks for sharing Stilletto. When I decide to tell someone I'm interested in about my passion, which can include wearing things other than heels but not often, Its usually even before we've met. I just feel that I'm obligated to let someone know upfront about who I am, in all honesty. Since I don't heel publicly I never had the opportunity to "show" my interest until things get a bit more serious and we start getting together privately.

[Shafted]

She needs to know as soon as humanly possible. Don't make the same mistake others here have. Is all you need to do is read the past stories and know that what I'm saying is true. If she has an issue with it, then she's not for you. You part ways with no damage.

[gallux]

When I first met my wife, I did not even think of telling her about my heeling, it was still not a big thing for me at that time... I tried to give some hints to her some times, such as shopping a whole day with her at a female shoe only mall, twice, telling her my tastes and all... but I froze when she asked me: "You do like heels too much... you don't like to wear them too, do you?"... I just denied quickly, the way she asked was too inquisitive... after that, never again I had some opening to talk about this... to her, I am just a "heel in female feet lover" If I were to meet her again, or any other woman, I guess today it would be different... in the first opportunity I would shoot something more incisive to see the reaction and then spit it all to her... it is too bad to live hiding this topic... horrible thing when you cannot do what you want... it is like "being in jail"... And I agree with Shafted... don't commit to the same mistake I did... the more you are involved with the woman, the more difficult and less opportunity you will have to reveal this...

[HighHeelLover86]

My heart goes out to you gallux. I would whole-heartedly agree Shafted. Since I rarely ever meet someone new without exchanging some form of communication for a while first these days, nine times outta ten I mention it before a face to face meeting. Also even if they sound accepting of it, if I were to wear heels on a first date I would ask them about it first just to make sure that I didn't go to fast with it if they have any hesitaiton on how they feel about it. I have found that if you go slow with it and are clever and caring enough about how you approach the subject, more often than not they will at least accept it and at most love it. I have never been in a relationship that I was not at least minimally accepted, even if i was restricted to private heeling only. I guess I'm one of the lucky ones.

[ilikekicks]

If your doing the ' online dating ' entity, why not put a comment like ' I enjoy freestyle fashion ' in your info/comments? Many women ( or men ) wont even know what such is and it might even spark up a conversation to get to know one another? As Shafted said, ' As soon as humanly possible ' is the best way to go about it. No baggage or worries right from the start. Does it possibly chase away a few prospects? No doubt. Better they arent around if they cant fathom something as simple as what you have on your feet or what you wear. There are ways to use your choice of footwear to your advantage when dating. I mean, how many women can actually sit with a guy and talk about footwear? Thats a whole area of conversation you can jump right into. Most men.. they would fall on their face ( without the stilettos even on their feet! )

[HighHeelLover86]

I concur ILK. I try to reveal it before a face to face meeting if at all posssible. My big thing is that my heeling started out as purely a fetsh ans even though it has/is evolving into a fashion for me, its still very much a fetish too. That can make the discussion somewhat more touchy.

[AZShoeNut]

Howdy, Well, I told my wife on our third date. I was looking for something long term when I started dating my wife. I didn't know exactly how I was going to tell her but I knew it had to come up earlier than later. On our third date she was wearing some boots with about a three inch block heel. They were not something that I would have found amazing. She kept apologizing for the sound, the height, etc. I replied with "no problem," and then later "really, no problem." Even later in the evening back at my condo we were on the couch and she apologized for the solid thud that they made heel hit my leg. I said something to the effect of, "Really no problem. I have to tell you that I dig high heels. Let me be clear, I really dig high heels. I own several pairs and I like to wear them." It kind of took her aback. We continued to have a nice time that evening and she went home. A day or two later when I talked to her again she said that she thought about it, remarked about the qualities that she really liked about me and decided that the qualities that she liked outweighed this unusual aspect about me. She decided to see how things would go from there. So, In December that will have been 10 years ago. She accepted it at that point and was fairly open minded about things all along. When I started to want to wear my heels out and about then everything got pretty complicated. As I made efforts to try to bring public heeling about I would hit a solid, dead, hard wall. At points I thought that if I wanted to wear heels out and about that I could lose my marriage. Last September - October I started wearing my heels out and about - mostly for coffee in the morning before work. She did not warm up to it very quickly however she did start to warm up. At Christmas she gave me a gift certificate to the coffee house where I wear my heels. That was the first vote of support that I received from her. Still not sure where things will end up. I did ask her if she wanted to join me at the charity walk at the end of February and rather than saying no right away she said that she would think about it. I personally doubt that she will however it is still evidence that she is still warming up to it. I wish that I had been more aware of how my interests in heels would grow and change and expressed that in the beginning. In more recent discussions with my wife about my heels I have pointed out that I was up front with this from the beginning and she replied pointing out that in the beginning I did not include going out in public as part of the deal. At that time I seriously never thought that I would go out in public in heels but now it is pretty darn important to me to do so. So, I guess that if I had to sum it up from my experience, I would say get it out on the early and be clear that the experience can be somewhat open ended. Best, Larry

[HighHeelLover86]

Thanks so much for sharing larry, and all of you thus far. I think I'm a wee bit backwards from you in a way Larry. I use to wear heels in public quite a bit but fell out of practice due in no small part to some incidents that occured. i have a trememdous desire to do it again but I'll admit, it would be a lot easier to have someone in my life backing me up. I'll also admit, as I have done in a few other posts, that I may be more open than some about "coming out" as it were, because a part of me really does enjoy that initial shock factor, no matter how small it may be. A scenario often played out in my head is after things move along enough that we routinely meet privately, if I haven't really told her yet i might say something like, "I really admire those shoes/boots you're wearing, what's your size?" and carry on from there.

[Bubba136]

A good rule of thumb that you might find helpful would to tell any person about your high heels when it becomes obvious that your relationship is going to be more than the normal/standard boyfriend/girlfriend dating friendship. Any lifetime relationship is built on trust. And, should your partner discover, or find out after the fact, the entire rest of your life might be forever altered. I met my wife on our first day at college. Told her about my heels around Christmas break. Took her until March to sort it out to the point that she was "comfortable" with the idea. That was three children and 7 grandchildren ago.

[Steve63130]

It took my wife 20 years to be comfortable with the idea of me wearing heels, much less in public, and even then only heels that aren't highly feminine. I restrict myself to boots, clogs, and some sandals. No stilettos, but I do have a couple of pairs of booties that have a heel about an inch thick or so. I'm happy with the compromise and so is she, and we're going on 39 years together, so I think it's a workable solution. Steve

[HappyinHeels]

HighHeelLover86,

Lots of good advice here and you'd be wise to fuse it all together to make a better decision next time. Listen to Shafted, he's wise beyond his heels, and let any prospective partner know of your "expanded fashion tastes" as early on as possible..If someone cannot see the content of your character because they cannot see past your heels then they are too shallow to have the qualities you seek in a partner. Effective communication is the master key that opens the doors to fulfilling relationships. Tell prospective partners you are as willing to accept tattoos on women as they are to accept heels on a man. Effective communication is so important and confident people are almost always effective communicators. HappyinHeels

[niknhose]

I would agree with the posts so far, the earlier in the relationship the better. If she doesn't accept it then neither of you have invested months or years into the relationship. The last 4 relationsips I have been in, I have been up front with the women within the first couple of weeks. All of them were accepting of it. My last relationship is my current wife of coming up on 8 years. While she does accept me and the fact that I wear heels, she would prefer me to be more 'manly man'. Actually, I guess that would make it more tolerence than acceptance. I will take what I can get with her. My sister-in-law however is alot more accepting of it and has even threatened to take me out dress shopping. If I were to re-enter the dating scene again however, my heels would probably be the first topic of conversation or not mentioned at all becuase they already knew. Nikki

[HighHeelLover86]

I'm currently talking to a couple of people online and within maybe the first 24 hours of so I explain my tastes to them. It seems to be going fine so far. I wasn't really looking for advice for myself so much as trying to get a general concensus but all of you have great advice and I appreciate it all the same. I hope to here some more from you guys, being back here is truly giving me that boost I was hoping it would.

[hh_pe]

My view point is the same as everyone else, as soon as possible is the best. My wife has always been very supportive, but has set some rules too. Open and honest communication has always been the foundation of our relationship. I don't remember how soon it was after we started dating, but I do remember telling her earily in the relationship.

[Foxyheels]

I told MrsF within 10 days and got the reply "that's ok". Clearly I had been lucky and found myself an absolute gem and I am wonderfully happy to this day and regularly wear heels out and about with her, alone and at work. I sincerely hope I never have t go through the dating process ever again but if I did and had to join an on line agency then I would make it part of my profile. I would ensure anyone who communicated with me would know about it straight away. This would filter out the ones who would never accept it. I have found that most women love the fact I like shoes and shopping, yes they are surprised because let's face it, it is unusual but there are many who can deal with it logically once the initial surprise goes. Th other bonus is that most heel loving women tend t be very feminine which is jus my type. Very good luck on your search for a partner, as others have said the earlier the better as it's easy to walk away from a girl you hav only known a few days, I gets harder when it becomes weeks and months and then you make compromises to your character that could store up trouble for h future.

[HighHeelLover86]

Yea i'm considering going out in heels for the first time in public in years on a date i have friday with one of these women. nothing outlandish just my fave pair of chunky stacked 3.5 inch ankle boots. It would be a two fold thing and I feel might gauge the situation but I'm not sure

[Jimnj3]

At this point in my life I would just go out on the date in the heels you describe. They don't sound like they would attract much attention. Just be yourself and don't try to think in your head as to what will happen. It usually is just in your head. Just wear them as if they are everyday shoes and see how it goes and if she has any comments. This way she will see/know right off the start as to what type of style you have. Nerves get the best of us.

[SF]

I have worn women's shoes (flat sandals) since I was a teen. When I met my (future) wife she well aware of my "habit." As we got to know each other better I even bought her some matching sandals that we wore together. She did ask me why I wore women's sandals and I just told her that I liked them, and she accepted that. We got married and I continued to wear women's sandals and buy her sandals as well. I never really noticed or had a passion for heels until 1996 when I made a trip to Argentina. There I noticed the women wearing goreueous heeled sandals that were elegant and classy. One of my (female) traveling companions (it was a business trip) was into shoes and she was always commenting on the high heels that the Argentine women were wearing. She even bought a few pair. This experience got me paying attention to high heels more. When I returned to the US I found myself one day browsing a shoe store (like I had done since a teen) looking for some flat sandals. I saw a few pairs of heeled sandals that looked nice - and in my size. I tried several pair on and from that moment I was hooked! The look and feel (I had NEVER worn heels before) of the sandals were fantastic. I bought one pair - I actually still have them - and on the way home was thinking how am I going to tell my wife, what is she going to think, how is she going to react?? I did not tell her about my purchase for a few days, as I thought this through. I decided the best way to tell her was to just - tell her. When she was in the front yard gardening, I put on the heels and walked out and asked her what she was doing. She initially did not see the shoes for a few seconds, then looked at my feet and asked what I was wearing. She wasn't angry, but definitely a bit surprised. I told her that I saw these sandals, and liked them. That was the beginning of my high heel experience with my wife. Since then I have been a happy heeler with about 25+ pairs of heels and a wife who accepts my heeling. Frankly, she isn't 100% in favor of me in heels but understands that it is something that I enjoy. Now I buy her heeled sandals too and she loves it! Heck, she has even bought me several pairs of heels!! So, short story long, try and tell you g/f wife, whoever - the truth as soon as possible, keeping heeling a secret will probably just make things difficult. I do understand and have sympathy for the folks who have a spouse or significant other that is adamantly against heeling, hopefully those issues can get worked out over time.... Anyway, I'll shut up and post this, take care all. Hare Krishna, Crash Pads, and Power to the People!! sf..

[HighHeelLover86]

Update...

All seems well with both women that I'm interested in seeing. If fact one has hinted at maybe thinking its cool, or even hot! both seem to have a genuine belief that everyone should be who they are and not care what anyone thinks so score and score. The one I have a date with Friday insists I wear my aforementioned boots. So now to try and get past my housemate (aka my aunt) without a snide comment. This could get interesting!

[Amanda]

If you're preferred dating method is via dating websites and you wish to find a woman who percieves male heel wearing to be "hot", you should consider posting a profile picture of yourself in heels. That way you would efficiently screen out all those women who didn't fancy the idea, therefore saving both of you from any awkward moments or embarrassment.

[Amanda]

Actually, I would recommend against posting a picture of you heels online. Then the whole differences between the IDEA vs. REALITY of a man in heels will kick in. Instead of her responding to all the information that constitute Real World Communication like non-verbal body language (the artistic motion of your body when you walk in heels, your better posture when you wear heels), voice tone, voice pitch, voice volume and speech rates, and general public non-response to a guy in heels (the experience that most people don't really care, it doesn't kill true status you may already have), you unjustly subject her to the flat, one dimensional data of her own imagination. It's not fair to you or fair to her to discern the possible furtherance of a relationship upon speculative imagination. It's better for both to do so based on real world experience. The long term benefits of truth in this case outweigh the short-term effect of any possible social embarrassment.

Spoilsport

[HighHeelLover86]

Thank you guys and gals for being so supportive. I am so SO glad I came back home to HHP. I can't express how thankful I am that all the feedback and all the advice and thoughts shared on this post and throughout the site have truly given me that extra push I was seeking in my quest to truly LIVE. To find people that are truly compassionate in any light is a rarity in my life. Its been a hard night of introversion in case you guys were wondering why I might be a bit emotional right now. Tiffany, a woman I've plans to start seeing from a dating site, have been talking for hours every night this week. A full on perfect match so far not just regarding my heels of course but also in so many other ways. It might sound funny but after the conversation we had tonight, like we've had the last four nights, I sent her my Amazon wishlist full of heel choices I've picked out. She left a very pleasant e-mail this morning with a few choices of her own, not only for her but for ME TOO. I'm just gonna take it day by day so don't think I'm ready for the "I love you"s already. At this point though. Its such a perfect fit that if she asked me to take things to a serious relationship right now I don't think I could say no. If months and years from now I find myself with her I can't say I'd be unhappy. Anyway I'm gonna end this post before I ramble another two or three paragraphs. Hopefully I didn't sound too much like a high school freshman lol.

[Jimnj3]

I wish you good luck! Sounds promising! Keep us informed, please.

[Foxyheels]

Spoilsport

As I mentioned in my post I totally agree with you Amanda I would be up front about to filter down any replies to those who were instantly ok with it but as I said I hope I am never in a position to have to be looking for a partner.

[Steve63130]

Amanda and Kneehighs, You both bring up interesting points, and I'm not sure your positions are mutually exclusive. There may be a middle ground. When a guy says he likes to wear "heels," what he means could be interpreted in so many ways, because there are so many kinds of heels. One scenario is that he could take a pic of himself in block heeled boots, for example, that would not put off any but the most conservative women. The caption or accompanying description could mention that he likes shoes with a higher heel without going into detail. Once he meets the woman in person, discussion could move in the direction of more femme shoes, if the woman seems comfortable with it. But I'm afraid that if the initial photo is of a guy in stiletto pumps or plats, then I agree that Kneehighs statement about idea vs reality will kick in and I suspect most women will go "Ewwww." But, on the other foot, that could be a wonderfully efficient filter for sorting out women who can't accept guys in femme heels. Surely there would be one or two women who see that photo and think a guy that wears stilettos is a super confident dude, and confidence is sexy! And we all know that Kneehighs is living proof of that! So my thinking (and you get what you pay for! lol) is that you could go any way you want, with no mention of heels or with a photo of you in stilettos (at either extreme) or with a photo of you in more conservative heels (middle ground). Steve

[Histiletto]

The shock of men wearing heels has lessened due to the media articles about guys wearing heels, some of the celebrities performing with stiletto heeled males, and many of the internet sites like You Tube and tumblr have pictures and videos depicting males in "women's" high heels. Many of the internet comment sites have a lot of posts concerning high heeled men, the men wanting to wear high heels, and/or the participant's perception on men in heels. So the idea of men wearing heels is not as foreign to social thinking as it was even ten years ago. Much of social attitude adjustment towards men in heels has to be credited to this very forum - The High Heel Place, for we have both female and male members, world wide, expressing their desires for heeling privately and publicly. So telling the girl of your dreams about your desire to wear heels isn't as monumental for the relationship as it use to be, because of the social awareness being available for all to consider. Once everyone understands the desire for wearing high heels is and has been as common to men as it has been and is for women, the better relationships will be able to proceed successfully. Of course, the way it is dealt has to be done with intregrity, with as full a disclosure as possible, and with a sense of humor before either one becomes emotionly connected so that everyone can understand the situation they are deciding whether or not to become totally involved with. The question of one's love and loyalties often comes with this situation. The male heeler can't deny his connection to or desire for heels isn't important for it is a part of his personality just as much as his demeanor, talents and other yearnings for fulfillment. Female heelers also have similar personalities that hold the wearing of heels just as important. The soulmate has to see that their position also has great importance and that having a relationship is going to be beneficial for both of them. There is such a thing as the attractivenes factor, which lets two individuals know they want to be with each other before any promises come into play. This is a key for beginning relationships, but the continuation of the courting rituals and effective communications with loving interactions bring the joy meant to be part of these evolving commitments. Obviously, the wearing of heels hasn't been an only female desire. It is a personal choice that brings satisfaction to the one choosing. Anyone that cares for another person wants them to enjoy life and if wearing heels or any personal adornment desires are part of their personality, those that care would want them to share in their joy. Notice that this is also not gender specific, for women as well as men have desires and needs to be satisfied. Society may have tried to segregate the wearing of heels through its rules and decrees, but this hasn't and doesn't remove the desire men have.

[HighHeelLover86]

So much love and so many great and intelligent comments thank you. I was planning on wearing my fave boots on my date but apparently my feet have gotten bigger. On a disappointing side note this means that's virtually all my heels now may not fit. A very sad sad day indeed. The good news is that my date and i both share a love of the high heeled shoe and even the same tastes so I think at least the heel thing is going to work out just fine. The rest seems to be great too but i am trying to keep myself grounded for the time being. She did suggest that should we both want another date after tomorrow night that perhaps we'd both enjoy a trip to one of the larger cities in our region to go to Torrid and indulge in a little bit of shoe nirvana. At any rate I'm uber excited I promise to keep up with the updates. Oh and for anyone who likes sexy shoe picks I found a Facebook page called Shoe Box Porn that's full of them, just FYI.

[Bubba136]

Be aware. Don't take it to fast. If it seems to good to be true, it probably is. I do wish you good fortune,though.