We are going to have an honest discussion of dating and underwear. I have asked Bikinisnthongs to join me in this debate. We are approaching this from the gay side of the issue, but we think all guys will see similarities in our journey.

UNB Tim – Welcome to the talk. I invited you to this because I love your honesty and perspective on underwear. I haven’t dated in 11 years. Now I want to venture back in the waters of the dating pool. When did you last seriously date?

Bikinisnthongs – Thank you for inviting me!  I last dated was about three years ago, but it was a bit unconventional.  I met a married gay couple and joined their relationship.  It ended when one asked the other for a divorce.  What are your plans for getting back out there?  

UNB Tim – That sounds like a fascinating time. I have met more people dating couples in the last year. I guess it’s a trend in the gay world. I call them a “thruple.” I’m not sure that is for me. Well, the plans are the issue. I hate online dating with a passion and the so-called “Dating apps.” It’s always “Looking?” “X pics?” and all-time favorite “Let’s fuck.” For the time being, I am asking friends if they know any single good guys. So far the response is “You wouldn’t like the single guys I know.” Another WTF moment. Who are my friends hanging out with? It’s a chore! Wish me luck I will need it! But let’s talk about underwear and dating. We have had many offline conversations about underwear. What do you consider “date night” underwear? Does it change due the date (such as the first date vs. 5th date)?

BnT – “Date night” underwear for me is any pair that makes me feel sexy and comfortable.  Usually, that’s a bikini or thong, but I have also worn more conservative pairs like briefs or trunks.  I will admit that I have tailored my underwear choice to the preferences of my date, rather than wear a pair that would make me feel the most comfortable and sexy.  What do you typically wear on dates?

Tim – My “Date night” undies are more about me than my date. I know that may sound selfish but its what I have always done. And I do things in reverse. The first date I wear something super sexy, well to me. On the date I know I’m wearing something awesome. It gives me a bit of a confidence boost. It’s rare that I get naked on the first date. As the dates go on and the “pants come off moments” I wear something, not over the top. A nice bikini or something. However, since I last dated, running an underwear blog is not a topic of conversation early on. For the most part, guys find it cool and it makes wearing sexy undies, not such a shock. I’m curious, why do you tailor your underwear to what your date likes?

BnT – I think I’ve done it to wear what would please them or not turn them off.  I have dated several guys who didn’t like thongs or bikinis, so I didn’t wear them while with those guys.  I actually had one guy laugh at me when I got undressed and was wearing a bikini.  I felt sexy, but a little humiliated.  I wore briefs when with him from that point forward.  He wasn’t a great guy, to begin with – I know that now.  So lately, I wear what I want.  If the guy doesn’t appreciate it, then it’s his choice not to be with me, but I won’t change what I like to wear any longer.  Have you had any bad experiences with a guy you’ve dated not liking the underwear you were wearing?

UNB Tim – Glad to hear you are wearing what you want! I think we all should. I can’t think of any times I dated that someone said a negative comment to me. I’ve always tried to get the person I date into what I am wearing. I guess I bring them in and let them help me pick new undies. My longest term relationship he would actively suggest things for me to wear. Which I loved! I haven’t ever found a partner/boyfriend who was also into underwear like I have been. They seem to be rare. Which is odd considering I run an underwear blog! Anyone reading out there single LOL. Let’s talk first dates! Say you meet a guy, and you agree to go out. Like I said I go for something super sexy and fun on the first date. I’m to the point where I am not after a quick fling, and it’s very rare we get naked on the first date. I have worn skimpy bikinis, Cocksox CX01’s, Jocks and such. What is your typical first date pair/style?

BnT:  I am always super nervous on first dates!  I tend to pick a pair that makes me feel sexy, yet is comfortable and familiar.  It’s rare that my date would get to see them on a first date (maybe that’s why I don’t get many second date invitations?  LOL), so the pair I wear is just for me.  The style I wear somewhat depends on what we’re planning and what I will wear otherwise.  If we’re going to be active in some way or my pants will be more fitted, I wear a thong – one of my Gary Majdell Sports thong or a JM Skinz.  Otherwise, I might slip on a classic black bikini – I have several from N2N and even one from Andrew Christian that I like.  

I have also tried to influence my boyfriends’ underwear choices, with varied success.  I’ve had the most luck when taking smaller steps like introducing them to new brands or a new fabric (other than the typical 100% cotton, K-Mart special boxer briefs) that aren’t super expensive.  Once they get a feel for the improved quality, then they’re more likely and eager to try more and experiment.

How long do you typically wait before trying to make influence a guy’s underwear choices?  It may be a little different for you since you run this blog.  😉

UNB Tim – I’m right there with you with second date invitations. I was the king of first dates. Well, since I haven’t dated since I started the blog. My last really serious relationship was in 2006. UNB began in 2008, I’ve had first dates but nothing really serious. After a few dates when I know it’s getting serious, more than let’s hang out. I start having the undies talk with them. Especially if they are wearing underwear from big box stores. Those have to go or even worse boxers. I mean nothing kills a mood for me more than getting to sexy time and see baggy no form boxers on a guy. I remember asking one “seriously, this is what you wear to a date you know you’re getting lucky?” The sad thing was he didn’t see a problem with it. Undies were to come off not be worn for your partner.

After we have a talk, I break them in pretty easy. I mean, I”m not going to buy them a thong right off the bat. If they are wearing boxer briefs, I get them some nice CK boxer briefs. Something tighter and has a form to it. If they respond positively. So far, all the guys I have changed undies have, then I suggest and buy smaller things. I have had past boyfriends go from boxers to briefs but never had much luck getting them into bikinis or thongs. Occasionally they will wear a jock but its always something secondary. When they have worn something sexy its been like an anniversary or my birthday because they know I will love it. But it’s never in their regular rotation.

I’m curious as to how the blog will figure into the dating thing. I’m pretty upfront and honest about it. For the most part, guys are impressed that I built something on a passion of mine. I have had very few think its weird or strange. I have had more of the “OMG I love underwear too” after I tell them. It’s like having a love of undies is a thing we should hide. So my question back to you is how much of an influence have you had over guys you have dated? Have you had any luck getting them in thongs or bikinis that you love?

BnT:  My influence has been limited, unfortunately.  The last guy I dated started to wear some sexier briefs, but I never got him to the bikini or thong stage.  We’re still friends (and soon to be roommates), and sometimes I’ll catch a glimpse of what he’s wearing, and it’s the more fashionable briefs. I don’t know if he wears them when he’ll be around me or I’d he’s changed his preferences completely.  He did lose a bit of weight so maybe these pairs fit him better.  I’ve never really asked him about it.

My very first real boyfriend (over 20 years ago) did make a dramatic change, at least temporarily.  He went from loose boxers to sheer mesh bikinis pretty much all on his own.  They were the sexiest he could find at the local Target.  Ha!  I still sometimes wonder if he’s gone back to boxers or settled somewhere in the middle.

I have had more luck with a friend with benefits.  We decided to include underwear as part of our fun one night, so I put him in a thong.  He loved it.  He ended up borrowing a few of mine until he could buy some of his own.  We still chat occasionally, and he’s pretty much converted to wearing thongs all the time.

What’s a guy’s typical reaction when you try to get them to try a thong?

UNB Tim – Nice, well me it’s pretty much hit or miss. I think it’s more miss than hit. I have had better luck getting guys in bikinis rather than thongs. I”m trying to remember when I got a boyfriend in thongs. I can’t recall. I think it was more friend with benefits. Which makes no sense the boyfriend should be more open to wearing what turns you on.

Most boyfriends have looked at me like I was crazy for suggesting a thong. I think it mirrors the society in general. Thongs are viewed as feminine. Which I don’t get how a pair of underwear is feminine but that’s another whole discussion. Handing a boyfriend a thong and say wear this, and they give you a strange look. I am the kind of person I like to do things that my partner will like. I expect the same in return. It’s very much give and take with me. I think I have grown and not the same person when I dated before. I know what I want and the next guy will be open to wearing whatever because when they do, they get rewarded big time!

So what do you do when you the guy you’re dating, won’t or refuses to wear underwear you think he will look great in?

BnT:  Personally, I think a friend with benefits is more likely to try a thong for someone because of the situation.  It’s easier for them to wear it for playtime, then put their own underwear back on after.  A boyfriend knows that you wear them all the time and probably feels like they’d want you to do the same.  

You touched on a good point. The stigma of wearing a thong is a lot of why many guys look at you funny when you ask them to wear one or when they find out you wear one.  I always try to explain to guys how much a thong is like a jock – which is quintessentially masculine.

If a guy won’t wear what I suggest, then I don’t push it.  I do try to get them to at least try it on, but if they resist I drop it.  I don’t want to risk alienating them.  But I do know that if they try them on once, it’s likely that they’ll try one again and maybe for longer than a quick modeling for my benefit.  The trick is to get them to try it on and make it seem like it’s their idea.  😉

Are there specific brands or pairs you think are best for a guy’s first time trying a bikini or thong?

UNB Tim:  There are some great starter brands out there. My last boyfriend, I introduced him to Mundo Unico. He liked the pouch of the briefs I wore. I think one of the best bikinis that fit great and aren’t too much of a leap are the ones made by 2(X)ist. They aren’t too pouchy or skimpy. They give a bit more coverage than the kinds we like. I think they would be a great first step for a guy.

As for thong, I would go with my all-time favorite thong. The 2(X)ist Y-Back thong. It’s one of the first ones I fell in love with and still have! And surprisingly 2(X)ist brought them back. It’s one we have consistently named on UNB as the best starter thong.

I was going to recommend a bikini from Calvin Klein but I couldn’t find it on their site. It was made out of the softest material and fit amazing. But I think either brand are great starter brands for any guy who is buying their underwear in six packs (or more) at a big box store.

To get a guy go full on bikini or thong has been hard. I have had better luck bringing guys in on trunks. Since most of them wore boxer briefs. It’s the gateway drug as I call it. They get hooked on the good fit then I sneak in a brief and then finally bikinis and thongs.

What is your big success story with an ex. Did you get him in a thong or did you have to use the gateway boxer brief?

BnT:  I have a couple of the 2(X)Ist thongs – I even thing I have one in cotton and one in micro modal when they first came out.  I agree that they are a good first thong; I just wish they had more color options.  I have a couple of 2(X)Ist jocks, but never tried their bikinis.  Maybe I should.  😉

I also think I have one of the CK bikinis you mentioned.  It’s one of the classic black bikinis I like to wear on dates.  Oddly enough, I think that is the only pair of CK I own!  

I kind of talked about my one “success” story above.  I got him to wear a better quality of brief – low rise, better quality material, even some “wild” prints.  I did buy him a thong; he wore it a couple times to surprise me in bed, but it never stayed on very long.    Looking back, I’m a little surprised he didn’t wear it more often.  He certainly enjoyed how much it turned me on to see him wearing it.  The fun he could have had teasing me with it.  Haha

Have you ever been on a date with a guy who was already wearing a thong or skimpy bikini?

UNBTim – For dating, never. All of my ex’s were never into underwear nor did they wear anything that readers of UNB consider good underwear. It’s odd, you think more guys would be into underwear but it seems to be a smaller subset of guys.

So to wrap up our discussion, what advice do you give guys about dating and underwear when you have a partner who is not into it?

BnT: Run the other way?!?  LOL.

No, seriously, if sexy (however you define that) underwear is important to you, have a conversation with your man about it.  He may not immediately jump to wearing thongs to the beach, but they might take little steps to improving what they wear.  If he is dead set on wearing loose boxers, then you have to decide whether you like the guy or underwear more!

Tim: I couldn’t have said it better myself


Tim is the founder and editor of Underwear News Briefs. He has been an avid underwear fan since the age of 14! He founded UNB in 2008 and has continued to broaden his underwear love over the years

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