Ask Smitty

A guy's perspective on women's relationship questions.

Other Fish in the Sea


I’m going away later in the year on a once in a lifetime trip. My boyfriend promised to come out and meet me halfway through as I was planning on scuba diving and he wants to learn as well. However we still haven’t taken lessons and he can barely swim. He keeps putting it off repeatedly and making excuses, meanwhile prices for flights etc. are going up up up. I have turned down the chance to spend that week with the other people on my trip and now realistically it’s looking like we won’t get to go. I’m really upset and he won’t even talk about it and just tells me to stop throwing a ‘bitch fit’ about it. He won’t understand that we’re busy people, there will always be a reason not to learn to dive and he talks about how we will prioritize it but never actually does so.

– Rach



I’m sorry to hear your boyfriend is turning what sounds like an awesome opportunity into a stress fest.  My answer to your question is two steps.

Step 1:

Ask him to sit down because you want to talk about something important and ask that he waits until you finish before he responds.  Then explain how much this once in a lifetime opportunity means to you.  Tell him that you need him to stop demeaning your concerns by calling them a “bitch fit” and instead you need him to follow-through on the “prioritization” he keeps mentioning by booking lessons and buying plane tickets.  Say that if he really doesn’t want to go, even though he promised you, then he needs to offer a real explanation of why and not just excuses.

If he blows you off, offers more dumb excuses, or basically just continues acting the way he has been, move on to Step 2.

Step 2:

Dump his ass. Seriously. Telling you are throwing a “bitch fit” isn’t cool. Breaking promises and ignoring your valid concerns are not signs that he values your feelings. Refusing to talk about things means he doesn’t care at all about what you want. Then book the trip yourself and go meet a sexy scuba instructor.

– Smitty


Aural Sex

Dear Smitty,

My boyfriend is on a business trip for 2 months and we are trying phone-sex. So far it has gone well, but I am running out of things to say, besides talking about blowing him and what not, what else can I say that will get the job done?

– Phone-Sex Fright


Dear Phone-Sex Fright,

First off, well done keeping things hot while your man is on the road!

To start, definitely ask him what he likes. There might be a bunch of fantasies that he hasn’t told you about yet. This might open things up for you when he gets back too.  I think the secret to a good sex life (whether in person or over the phone) is honesty and a willingness to experiment without judgment. I’m sure there are definitely things he likes that he hasn’t shared with you yet. Do your best to make him comfortable enough to open up about them.

As for some other ideas:

  • Try role-playing. Both of you could pretend to be somebody else on the phone and spice things up.
  • Instruct him. Guys are more literal then girls. You might be telling him you’re blowing him but it could be hard for him to reconcile that fantasy with him sitting alone in a hotel room.  Tell him how you want him to touch himself, how fast/hard you want him to stroke, etc.
  • Make it a little risky. Maybe tell him you want him to get off somewhere public (caveat, make sure it isn’t SO public he gets arrested or something!). Call him while he is out to dinner and tell him to go into a bathroom stall.
  • Along the same lines, make it spontaneous. Don’t always plan it. Surprise him with a call and tell him he needs to drop everything – starting with his pants.
  • Get him to be verbal as well. Ask him to tell you what he would be doing to you if you were there right now. Make sure you express how excited that’s making you.

Hopefully this will help you out over the next couple months!  Either way, I’m sure Alexander Graham Bell would be proud!

– Smitty

Crimes Against Your Mammaries

Dear Smitty,

How do I tell my boyfriend to be a bit more gentle on my boobs? He got a little carried away last night and now they hurt like hell!

– 2nd Base Pains


Dear 2nd Base Pains,

So he really loves your peaches but he’s shaking the tree a bit too hard, eh?  Luckily it should be fairly easy to put him on the right rack track.

You’re probably best off approaching the situation a lot more gently than he approaches your boobs. You don’t want to phrase this in a way that makes him question his prowess or become nervous in bed. Try keeping things light but honest: “Babe, I love how passionate you get when we have sex but you really did a number on my cans last time. Next time try to go a little easier on the girls!” Hopefully he’ll get it and respond accordingly.

If it keeps up however, you may have to be more firm in your breast request. Or, you could be a bit more subtle. During sex you can maneuver the melon felon to positions where he doesn’t have easy access to your tatas (like reverse cowgirl) or tell him you love it when he grabs you by the hips because it gets a more powerful thrust. You could even tell him you want to tie him up!

Whatever you do, don’t let this upper body karate from your boyfriend take the fun out of funbags!

– Smitty

The Talk

Dear Smitty,

I’ve been dating this guy for about 6 weeks now. We met online. 2 weeks ago we had the “talk” about exclusivity. He wanted to keep dating each other and other people. That was fine with me, but at what point do I broach the subject again and find out if he’s ready to just date me? Am I just wasting my time here?

– Single in the Midwest


 Dear Single in the Midwest,

There are really only two reasons why he doesn’t want to be exclusive.  The first is that he wants to play the field, sleep around, find something “better,” etc.  The second is that he doesn’t yet know you as well as he would like and is afraid of getting hurt or hurting you by jumping into things too soon.

So, I am going to answer your question with a few of my own.  How much time have you spent together in the past 6 weeks?  Have you only had one date or so a week?  Or have you been seeing each other every few days and been texting/calling/emailing in between?  Does he make plans in advance with you or does he wait until the last minute?  Have you met his friends yet?  Been to his place?  Spent a whole weekend together and not just a couple weekend nights?

Get the point? 

If things are moving in the right direction where you are starting to get to know more about him, he’s happy for you to meet his friends, and he make an effort to see lots of you then things are going well.  The “talk” will come up again naturally the more comfortable he gets with the idea of you in his life.

However, if you don’t hear from him for days at a time, haven’t learned too much about his friends or family and the relationship feels entirely too casual, then chances are there are a few other girls asking the same question about him right now.  In which case, be happy you’re not exclusive and go find someone better.

– Smitty

Radio Silence


I know this guy for close to 10 years as we went to high school together, and we’ve liked each other in some form since 10th grade. We are 24 and 26 now. We’ve been sleeping together on an off for the past 3 years, but hadn’t seen each other in 8 months since I moved across the country. He had a work conference last week, and I flew across the country to stay with him. Things seemed ok while we were together and he said he had fun, but I haven’t heard from him in the week since I got home, except that he ‘favorited’ one tweet I wrote. We don’t typically go more than a day or two without talking, and we’re currently going on our 7th day without speaking.

What gives?

– B



Let me preface this response by saying that with a 10 year relationship there is going to be a whole lot of background that I just don’t know or understand but I’ll try to do my best with the information you’ve provided.

First off, it’s possible he’s just been super busy.  Coming out of the conference maybe he’s just had a lot to catch up on back at work etc.  However, given that you “don’t typically go more than a day or two without talking” and this was the first time you’ve seen each other in 8 months, that’s probably not the case.

You say that you’ve “been sleeping together on an off for the past 3 years” not that you have dated on and off.  You’re in your mid 20s and I’m in my early 30s so maybe I’m just a little more old fashioned but I would think that after 3 years of sleeping together some form of commitment might have been explored.  Since it doesn’t sound like it was, my guess is that one or both of you are fairly independent and not looking for something serious. If that’s the case, going from not seeing each other for 8 months to staying together for a week can be somewhat jarring. (I’ve had good friends of ten years staying with me I was ready to see leave after 3 days.)  He may have been excited for you to visit but he may have been equally excited to have his space again.  That could either be a temporary change or a permanent one.

Here is what I think you should do.  If you haven’t already, reach out however you normally did before seeing him (phone call, text, email) just like you used to. Keep it light and don’t mention everything that’s been going through your mind.  If it was just a temporary need for space from you he’ll soon get back to you and be interacting as he normally has.

If it is a permanent change however, he may not get back to you at all for weeks or his responses may be different and more distant than they used to be.  If that’s the case, I think you are entitled to call him directly and bring up his change in behavior in a (this is important) neutral non-accusatory way.  Let him know that you sense things are different and you’re just curious why. Make sure you express that you realize things might have changed and that’s ok, but you just want to know how things stand.  Hopefully he’ll open up and you’ll get some insight one way or another.

– Smitty

A Mind Your Pee Q


Why do ALL guys end up peeing a little bit on the floor?  WHHHHYYYYYYYYY?  And when they do, why don’t they just wipe it up like a nice person?

– Lisa



Gee whiz, did you have to go there?  Sounds like urine a bit of a mess though.  Don’t worry, bladder things have happened.

To answer the first part of your question, there are lots of things that can impact aim. If the man has an erection it isn’t that easy to aim without contorting his whole body. Likewise, if he just had sex, some of those, uh, other fluids, can get in the way and alter the stream.  Even if the guy has sniper like aim, he can sometimes under or overestimate the pressure of his flow causing him to miss long or short.  (This happens more frequently as a man gets older).  Finally, and most importantly, there is drippage once he finishes and unless he’s over the bowl like the leaning tower of pee-sa this will end up on the floor.

The real issue I think is the second part.  When he does this, he should definitely be willing to wipe it up. (Just ask him how he would feel if you peed on the floor and he stepped in it).  However, he might have been living by himself or with other guys so long that he doesn’t even think about it or realize he does it in the first place.  In fact, the only reason I’ve thought about it is because my girlfriend called me out on it as well.  Hopefully, once you’ve pointed it out he will be more observant and wipe it up when he misses.  He might not always realize it or get it all clean, but any change in behavior will certainly be an improvement.

And, if he isn’t at least willing to consider making that change, then tell him to piss off!

– Smitty

Bad Joke or Insensitive Boyfriend?


I’ve been seeing a guy who is an expat living in my economically growing yet logically going backwards country. Our government–bear with me here–is revamping our outdated book of criminal code and they are mulling to regulate cohabiting couples, criminalize adulterers, and sexually active singles may get jailed.

Upon hearing such reports, this guy was like “maybe i should start dating my own people for the rest of my time here.”

He said he was just joking and apologized after I became upset. But I was infuriated and we ended up w/ a huge fight.

He said I was overreacting and taking out my frustration at the govt on him. Maybe he was right. But I stand my grounds and think he could have been more sensitive, especially knowing that these issues strike my angry cord.

What’s your perspective on this?

– You Know Who


Dear You Know Who,

Very interesting question for our first submission! Before we get to the relationship question, I want to encourage you to do your best to stay safe and sound given the rather draconian laws the country seems to be considering.

As for the guy, it certainly could have just been one ill-considered joke. The main thing to consider here is whether this is a pattern of behavior.  Will this happen again?

I think by nature men tend to be less empathetic than women. You say this guy knows that “these issues strike my angry cord” but honestly this guy may just not be picking up on how much the situation with the government upsets you.  I think you need to (as non-confrontationally as possible) communicate how deeply these potential laws distress you.  The goal shouldn’t be to castigate him for his joke, but explain your reaction to it.  If he cares about you he will listen to your concerns and work to understand how his actions affected you.  Then he will do his best to avoid any future jokes on the topic.

However, if it does happen again he is showing that he is either unable to listen to your concerns or unwilling to change his behavior to account for your valid feelings – especially if he continues to say you are “overreacting” and “taking out your frustration.”

In a nutshell: Guys often need things spelled out to them so explain how this is a sensitive issue and that you would appreciate it if he didn’t joke about it in the future. If it happens again after that you will need to address the fact that he doesn’t seem interested in understanding and respecting your feelings.

– Smitty

Ask Smitty your questions!

Why should I “Ask Smitty” anything?

ImageGreat question! To be honest, I can’t really say. The reason I have this blog is that my female friends are always coming to me for advice with their relationships and many have told me that they really find my advice valuable.  Mostly because I try to be honest without being judgmental.  Ultimately, I’m not really telling them to do this or do that, I’m just trying to explain why a guy is acting the way he’s acting. What they choose to do with that information is up to them.

As for my personal background: I’m a guy in my early 30’s living in NYC and in a loving relationship for some years now. I cohabitate with my girlfriend and her parakeet and I think we’re doing well!  My father worked a lot when I was young so I spent a lot of time with my two older sisters and my mom and I think it gave me some good perspective on women.

So If you’re confused by a guy, I might be able to help!  Or maybe you just want to vent. Either way, hopefully we’ll both get something positive out of this!

Ask Smitty Now!

p.s. If you’re a guy with a relationship question, don’t be afraid to ask away as well!