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You Asked: I Can't Tell if He's Kidding!

You Asked: I Can't Tell if He's Kidding!

Dear Sugar,

I recently met this guy who seems too good to be true. He's extremely attractive, exactly my type, intelligent, funny and single! We have been on a few dates but have only kissed. Everything seems to be going well, but one thing has been confusing/bothering me. Since one of our first dates, he has been making jokes and comments regarding having a small penis. I asked my friends about it and they figured he was just saying that because it is in fact big, and he wants to make me curious. He made another comment yesterday (probably his fifth) and I just couldn't take it anymore. I questioned him as to why he keeps talking about his small penis and asked if this was a normal joke topic among guys. He told me it wasn't a joke, it was in fact the truth. He said he'd rather I know now, before we have sex (which may happen in the near future) so I'm not surprised.

This attitude is confusing and totally unattractive. I don't know what to think — I've never dealt with a man with a small penis before and definitely not the insecurities that come along with it. I don't know how to react to his jokes, which continued immediately following our "talk." This is odd behavior to me and I'm wondering if this is a normal coping mechanism for guys lacking below the belt. What can I do to make him feel better about himself? — Perplexed Pam

To see DearSugar's answer,


Dear Perplexed Pam,

To be honest, I'm just as confused as you are! Since you're still in the getting-to-know-you phase, I would think that he'd be doing his best to show you all his good attributes, not wasting time cutting himself down. If he is in fact small, the only reason I'd think he'd continue to talk about it is that he's trying to lower your expectations so you're not disappointed when your relationship progresses to the next level.

I completely understand that his self-deprecating humor is both confusing and unattractive, so I think another little chat is in order. Tell him that talking about his penis size to soften the blow is actually doing the complete opposite. This is obviously an insecurity you cannot relate to, so keep reassuring him of your feelings and the next time he makes a jab at himself, try to stop him before he has a chance to finish. We all know the old saying, "It's not the size of the boat, it's the motion of the ocean," so hopefully his size, whatever it truly is, won't be an issue when you two finally become intimate. Good luck.


Join The Conversation
SeaAre86 SeaAre86 8 years
I'd have to agree. Girls do this a lot.. Although.. I think that we have a more subtle way of going about it. Coming from a guy, it's not surprising he's concerned about his penis. I mean, seriously, that is a guy's everything. I guess it'd be a little soon to bring it up.. but then again, how do you really bring that kind of thing up so it's comfortable? I think it'd be awkward and strange either way at first.
suelynn6 suelynn6 8 years
After 6 months of sex, I am still having a problem with my boyfriend, i love him very much but i do not enjoy intercourse with him because his penis is extremely large and fat making me uncomfortable and in pain sometimes.
thelorax thelorax 8 years
My friend dated this guy who would always crack jokes around our friends about his small penis...and according to my friend, it was actually very small. My personal experience...another guy who consistently would joke about his small penis...and it turned out to be on the larger side of average. He'd been scarred by an ex who told him it was small, and he believed her. So it could be either!
cokerad cokerad 8 years
I totally agree with karlotta, tell him to pull it out (if it comes out that far, ha ha ha sorry), so you can either tell him "It's fine stop grinding on your effed up insecurities" or "Okay, you're right, I can barely see it (followed by a "So see ya!" or "But it's fine")."
cubadog cubadog 8 years
For someone you are just dating to talk about their penis this much during the sweep you off your feet stage would be a huge turn-off and bad taste. That is a sure way not to see me again or to want to pursue anything with you!
karlotta karlotta 8 years
Next time he makes a joke, I would just tell him to whip it out and get it over with. I understand where he's coming from (and I dated a guy with a tiny penis, it was horrible for me, I had such trouble reaching orgasm - he probably felt really inadequate!) but he's being obnoxious. So tell him - hey, you want to lower my expectations? How about you set them straight right now, and show me what you've got. That should shut him up.
snowysakurasky snowysakurasky 8 years
"third time its just plain annoying and everything after that is just in bad taste" i agree! this guy seems very immature, how ever old he is. insecurities are not an excuse to be lewd with a lady that you are dating. i might even say something like, 'I'd rather not talk about genitalia for now, thanks, besides, how do you know you'll ever get the chance to sleep with me!?" and if girls make jokes about their small boobs, i do not think that is too appropriate either. if i really liked the guy, size would not be an issue, i think. one of my friends slept with a guy with a small dick, (apparently really small like 2 inches or less!), and she was still so crushed that the guy turned out to be a player. confidence goes a long way, but i agree that there must be women out there who place a high importance on penis size~(I'm thinking Samantha from satc)~
Jazz-Z Jazz-Z 8 years
I dated a guy once who seemed to have it all ~ the beautiful home, porsche, catamaran ~ the big dimples, the perfect smile, beautiful eyes, a body women would die to experience and men would sell their souls to have (okay getting carried away). The first indication he had an insecurity was when he casually mentioned he found skiing powder better than sex....personally skiing powder is pretty awesome but doesn't come close to good sex. On following dates he would make jokes about the size of his penis, and I can see why he would have a need to observe my reaction before getting too emotionally involved. I think size is very important to a lot of women and I'm sure its easier to have the women reject him after his declaration rather than when he's lying nude on the bed frustrated because he can't get a condom to stay on. If it doesn't matter, I would put his mind at ease early by reassuring him why that's not a problem for you or if it does matter, I would end it after the first revelation.
sparklestar sparklestar 8 years
I'd ask to see it. Size matters.
ckeller825 ckeller825 8 years
ew, I would be totally turned off by that comment. WHO in their right mind would mention something like this on the first date????? Gross!
courtneyh courtneyh 8 years
I like what Sun_Sun said about rolling your eyes and grunting. That's like a non confrontational way of saying "knock it off-you're annoying me!" Aside from you, bravo to you for sticking with him, I probably would have jumped ship already ;)
Jmartens Jmartens 8 years
It is odd that he is saying this stuff so often and so early. Size doesn't have to matter but it is strange that he is making it an issue at this point in the relationship. Be careful.
bransugar79 bransugar79 8 years
I think it's good that he can be open about it and honestly wouldn't you think it was weird that he was telling you he has a small penis no matter what way he did it. At this point you aren't in that space so it would be freaky if he just up and said we need to talk so he could tell you. Now that you know what's up you might suggest he stop making jokes but tell him there's no need to. Let him know you understand his apprehension but you like him so he doesn't need to make it an issue because it isn't. Guys are human just like us sometimes they just need reassurance that things are OK.
Sun_Sun Sun_Sun 8 years
once is weird twice its like ok i got the point third time its just plain annoying and everything after that is just in bad taste i would totally roll my eyes and grunt out of annoyingness if he does it again after ur "talk"
mondaymoos mondaymoos 8 years
I have to admit, if he's cracking jokes and being open about it, I wouldn't be worried about his "insecurities". If it bothers you that much, tell him to cut it with the jokes, but I wouldn't worry about the size of his penis effecting your relationship. There are lots of different positions, etc. to deal with guys who aren't as well endowed.
vmruby vmruby 8 years
If it bothers you so much then tell him you got the message and ask him to stop.....
gossipqueen gossipqueen 8 years
Girls do this ALL THE TIME! I don't know why is so 'confusing' when it comes from a guy. He feels his penis is not big enough...and jokes about it to 'soften the shock'...the same way an insecure girl jokes about 'love handles' or small boobs...people like this believe that if you know before hand you won't be shocked/disgusted so much that you dump them on the spot. How to deal with it....When you have sex, if you have sex treat it like a normal size penis (tho I don't know how small is small in his mind/body) If you like him for who he is...there are plenty of ways to get off with a small penis! If you're still together after sex or even just now...tell him to stop the jokes. Plain and simple. You like him for who he is and when you get to the sex part you'll deal with it.
designerel designerel 8 years
I guess this is just his way of warning you. I wouldn't be surprised if a lot of girls never called him again just because of size. And that has gotta hurt. I think a lot of size-challenged guys make up for it in other ways though ;) So if he is great in any other aspect I would give him a chance. I agree with Dear's advice to sit him down for a chat... hopefully that will lessen his anxiety and he'll stop cracking jokes about his size.
looseseal looseseal 8 years
I believe a slightly paraphrased recreation of this scene from "The Last Seduction" is in order. Bridget: "Let's see." Mike: "Excuse me?" Bridget: "I never buy anything sight unseen..." (unzips his fly)
jessie jessie 8 years
kudos for him for actually being honest with you, he's prolly lost relationships because of his "equipment." next time he trys to say something gently tell him that you don't like him putting himself down in any way. i just think he's telling you all this before you get into a full blown relationship. now its up to you with what you do with this info,....good luck to you! :)
sunnynight sunnynight 8 years
"It's not the size of the boat, it's the motion of the ocean"? I've never heard that before. =))
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