I went out with a guy about a year ago, who was a bit older and more established than me. To paint the picture, he owned a $2 million apartment on the UES (no not the UES-er) and wore a $10,000 watch, while I was living in a two bedroom apartment with a roommate. I didn’t date him for the money, but all of this is imperative to understanding how the events of our short-lived relationship unfolded. So we went out a few times and each time I had a lot of fun. For our third date he invited me to a nice dinner on a Saturday night. Up until this point we hadn’t had any sleepovers and our two previous dates were during the week, meaning I was wearing conservative, work attire. I was really looking forward to finally having a date in which work clothes and a cab ride home at the end of the night were not part of the equation. For the evening I planned on wearing a strapless dress so I decided to get some sexy strapless lingerie to go underneath. The date couldn’t have gone better, and by the end of the night we could barely keep our hands off of each other – I was dying for him to take me home. When we got back to his apartment and started hooking up he couldn’t find the zipper on my dress so I unzipped it feeling sexy and excited to reveal the black lace corset I was wearing underneath. To my surprise, when he saw my lingerie he said “why do you have so many layers on?”rather than “wow that’s hot” and jumping on me like I would expect any warm-blooded male to do. I was speechless and mortified…and totally turned off. I just wanted to put my dress back on and slink away I was so embarrassed, but I refused to be that girl, so I ignored his comment and continued on with where we left off. Within seconds his pants came off and there in the front of his boxers was a huge hole. No joke, probably 3 inches long over his right thigh. I was disgusted! Here I am in $200 lingerie (which he had the nerve to negatively comment on) in his $2 million apartment and he couldn’t buy a new pair of $5 boxers. Was he serious!? This is a 43 year old man- why did he not have fresh, clean (yes, I am assuming they are dirty if they are ripped) underwear?! After seeing that I did not want to touch him and got stiff and awkward. Let’s just say the night did not end to his benefit. My point, gentlemen, is that women really care about under garments for both you and themselves. We really don’t care if you wear boxers or boxer briefs (tighty whiteys are never a turn on, but I have seen some black and grey briefs that were hot – although I wouldn’t encourage wearing them the first time you are going to be with a woman), but whatever you are wearing should be clean and in tact. I mean, if you are that close to getting laid, why would you mess it up by not having normal underwear?! And I can assure you that women put a lot of thought into their bras and panties, so take a moment to acknowledge how good she looks in them- just simply say “wow” when you see her in them. Believe me, it will go a long way!!!
If you are looking for a good pair of boxers or boxer briefs, see my recommendations below. General rules to follow when buying underwear is to stay within the blue family for boxers and for boxer briefs stick to grey or black.
- For the classic boxers I would check out the Tommy Hilfiger solid vineyard woven boxer or Calvin Klein classic woven boxers
- For the classic boxer briefs, Jockey or Alfani
- For a higher-end brand boxer briefs, check out the Hugo Boss cotton boxer brief or cotton boxer shorts
- For the preppy guy, I would recommend the Vineyard Vine catboat boxers or the bonefish boxers (stick to the blue family, rather than the pinks and yellows)