Q: So I’ve known this guy for years and years and we’ve been friends for forever and we have “talked” before but nothing has ever really worked out. Well then months ago we start heating up again…finally hook up for the first time and things are going great. Then he moves to another city. Well now I see him every single weekend and we are great but he says he doesn’t want a relationship. I say fine no big deal I don’t want one either, but then he says he doesn’t want to mess around or kiss or anything because it makes him too attached and he doesn’t want to be a jerk and like someone more, mess around with them, etc if he doesn’t want to date them right now.

Well you would think that would be my answer right there but the plot thickens (lol). The past few weekends things have been getting more and more serious – I’ve met all of his friends in his new city, we have been hooking up, sleeping in the same bed, and pretty much acting like a couple without the title (which I’m actually fine with because if he’s not ready for the title I trust him and am not going to push him into it!). But he then proceeds to tell me one day when we’re having a “moment” that this was exactly what he didn’t want and now I feel bad for putting pressure on him.

So my question is….how do I proceed if he obviously really cares about me and I really care about him? Do I quit visiting? It’s definitely not going to work with me liking him and us being just friends and nothing else at this point, but then where does that leave the friendship?

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Got a question for Pillow Talk? Email pillow.talk.cc@gmail.com and we’ll tackle it next time!

Q: Okay, so I’m a guy, and I’m having trouble finding a girlfriend. I’m 20, about 6 foot, 165 lbs, average build, white (but not pale) skin, well groomed, short hair, shower daily. I’ve dated ten women, two serious relationships.  My most serious relationship was two years. I’m not really into sports, but if I’m hanging out with some friends and they’re watching a game, I’ll watch too.  I strongly believe in treating women with respect.

Generally on the first date I bring flowers, walk up to her door to pick her up, take her to her favorite food restaurant, always open the door (even car door) for her, and always pay (I don’t know why girls let guys get away with not paying). I’m more of the romantic nice guy than the hardcore-work-out-football-beer-blah type guy. I’m not into drugs, don’t smoke, and only have a drink occasionally. I hardly ever curse unless I’m mad. I use correct English but don’t correct others for not using it. I don’t have an accent or a lisp.

I’ve been told I’m attractive, hot, cute, average, normal, etc. I think I have a easy going personality, definitely not pushy. I smile a lot and always make eye contact. I love making people laugh, but most of all, helping them.  I have a few close friends, and enjoy small groups rather than large groups. I love to cuddle. I pleasure her before myself, or try, if you know what I mean. I don’t obsess over a relationship and call her all the time, and I don’t get jealous unless the relationship is threatened. I have a clean rep.

I’ve been on a few dates within the last few months, but none of them seemed to develop into anything more than just friends.  That spark never came.  I’ve talked to some girls that I know and asked them to dinner but they don’t seem interested in “that way.”

I’ve tried to think of everything that describes me.  I know it’s hard to figure this out without knowing me, but I do appreciate you trying.  Maybe I’m trying too hard?  Maybe I need to buy a motorcycle and become a bad-ass?  I dunno.  Can you give me any tips to improve my search for love?

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Q: I was wondering if you could go into the mechanics of shower sex in a college dorm… I’m sure it happens, but I was wondering, are there any disciplinary or even legal risks involved of bringing the opposite sex into your bathroom? Tips are also nice too!

A: I have to say, I don’t think shower sex is really all that great–dorm shower sex, even less so. But to each her own–here are the ten things you should know before sudsing up and getting down in the dorm showers:

1. It may be against the rules. Some schools keep women’s and men’s bathrooms separate, in which case, I assume sex in the showers wouldn’t be encouraged either. But hey, might be a great time to work out those bi-curious tendencies. Check your school’s rules–as far as I can tell, dorm shower sex isn’t illegal as a rule, so it’ll depend on your school’s policies–and then figure out how to break them!

2. Remember protection–condoms and flip-flops. You don’t want to catch an STD or a nasty fungus, so keep extremities covered.

3. Remove your eye makeup. I’m not kidding. If you take nothing else away from this, please remember to wipe off you eyeliner before you hook up in the shower. Yes, even the waterproof kind. Not. Pretty. Read More »

Q: I started dating a guy I was friends with for 1.5 years.  He asked me out forever, but I wasn’t ready after a bad breakup with an ex-bf. We went out on a handful of dates and then he got distant, so I pulled the plug and we stayed friends. I stopped contacting him.

One day in September I texted him. He claims he didn’t know it was me, so I started flirting with him and it drove him nuts trying to figure out who it was until he finally guessed it was me.  We got together again in November.  He asks me indirectly what else am I doing that week, he wants to see me again.  We got together again and he’s kissing me again in public.  I feel a little shy about it.  Then we make out at his house, but we don’t have sex.

We saw each other again in a few days.  I had to travel locally for work. I come back and we go out and again he kisses me rather hard in public – but we don’t go to his house.  But something changed and lately it’s been lunch type dates.  He also claims he’s had a cold on and off for 3 weeks.  It doesn’t stop him from hanging out with other friends and he doesn’t go to a doctor for it.  He said him saying he’s sick isn’t a hidden message, and that he wants to fondle me, but having a cold puts a damper on things.

I think I’m being blown off and he doesn’t want to hurt me.  I know that I don’t get to know the reasons why.  Though I have a pessimistic attitude b/c of some past experiences,  I’m diligent not to make that someone else’s burden to carry, however.  The problem: I think I started to fall in love here.  I want to believe he is telling me the truth, but my intuition says he’s being passive-aggressive.  I just wonder if this is my pessimism at work or should I spare myself some heartache and accept that he’s keeping me at a distance and move on to someone that wants to make more of an effort to see me?

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Q: I met a guy about six months ago, we hit it off and after a few weeks we started hooking up. At first we couldn’t keep our hands off each other, making out every chance we got and having sleepovers every weekend. The sex was amazing, but I never orgasmed. I still really enjoyed being with him, it just wouldn’t happen for us no matter what he did or how hard he tried. This went on for about a month and a half and then he started losing interest in messing around, now we only hook up about once a month. Could it have anything to do with the fact that he couldn’t make me orgasm? And why is that so important to guys? It’s not like he couldn’t make me feel good without that.

A: Oh, the ever-so-popular “wtf happened?” question. Without knowing every background detail of your relationship, I’d say, sure, maybe he’s distancing himself because he’s hung up on the big O. But we all know it can be pretty much anything. Guys fall off the face of the earth every day for every reason imaginable, and in my experience, it’s rarely for the reason we think.

You say you still hook up about once a month–who’s initiating these hookups? Is he still showing the same amount of enthusiasm? And most importantly, have the two of you ever talked about the (non)orgasm issue? I’ve been in your shoes–I’m not super easy to please, and it seems like some guys have trouble understanding that sex can be awesome for us without an orgasm, so I usually tend to mention it in a light-hearted way, either be saying something like “no worries, I’m hard to please, but we’ll get there” or by laughing about it if the dude is the first to make a joke about it. Read More »

Q: I’m a 23-year-old single girl. The other week, I met a great guy, and we had an amazing first date. We’ve been talking on the phone and via text since then since we’re both away for the holidays, but we’re planning on getting together when we get back into town. He’s smart, really sweet, and I’m really attracted to him. There’s just one problem…I’m having a lot of anxiety about my first time. I’m a virgin. I feel like it’s going to be so obvious to him if I don’t tell him beforehand, but if I do, he might be freaked out and have second thoughts about sleeping with me. What should I do?

A: Although I’m not exactly of the mind that your first time is/has to be the candlelit, looking-into-his-eyes, two-souls-connecting kind of sex, I do firmly believe you’ll both be better off if he knows that it is indeed your first time. And not just because it’s the “right” thing to do, although I do feel like he has the right to know, if only because that kind of lie is a rocky foundation on which to build a relationship (if that’s what you want to do).

But besides that, think about yourself! Sometimes, when two people sleep together for the first time, it’s hesitant, sweet, get-to-know-you sex. Sometimes it’s not and you’re up against the wall and swinging from the ceiling fan. Believe me, it would benefit you that your first time isn’t the latter. Yes, he should be sensitive to your needs anyway, whether or not you’re a virgin, but a little extra TLC wouldn’t hurt for your first time around–and he can’t necessarily provide that if he has no idea. Read More »

Q: As I sit here writing this, I’m confused at every feeling I am possibly feeling.. I have this “friend” we will call Fred. I had the biggest crush on Fred, even though he has a kid (this just makes me a bit uneasy, I’m only 21. I don’t want to be tied down like that if things did progress, but I regress.) I liked him, but he never seemed to initiate anything, but via texts he was flirty.

Two or three months went by and I was in a relationship that abruptly ended. Since nothing had progressed with Fred I felt like he was just a platonic friend and vented to him. He was amazingly supportive and said everything I wanted to hear (i.e. he was a real jerk, I don’t know what you ever saw in him, you deserve better, yadda yadda…). Well this kind of opened my eyes to Fred more and I developed a bit of a crush on him again.

He started coming over to my apartment to watch our favorite tv show. The first time we did this, we made out, things started getting intense and I ended it. He came over again and we made out again, but my roommate was here, so nothing else happened. When he left, we kissed and he promised he’d call and come pick me up the next day.

His plans changed, so we didn’t get together (but he had a good excuse, if that matters), then the next day I sent him a text and he responded, but not as quickly as he normally did. Now comes today, I didn’t text him to see if he would text me and he hasn’t. Am I being paranoid or is he trying to shoo me off?

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Q: I was dating a guy for a month when a conversation about one of his friends turned into a talk about “us.” It hadn’t been anything serious, but I said I think that seeing each other as often as we did, it really should evolve to a relationship. The boy panicked.

This is someone who called me half the time, took me for a fancy dinner on my birthday, WANTED to hang out, asked that I not hook up with others (and I know he wasn’t either) and actually liked me, and yet, there he was telling me he could never be a boyfriend to anyone right now and that maybe we shouldn’t hang out anymore. It was actually a really disturbing freak-out. We haven’t spoken since. What gives?

A: Oh man, we’ve all been there, haven’t we? He’s totally into it, but bolts when we try to take the natural step forward.

I’ve never been a great mind-reader so I decided to take your question to someone who might have a bit more insight into the male mind–my boyfriend. So what’s up with a guy that wants to act like a boyfriend until you actually say the word “boyfriend”? Read More »

Q: I’ve been dating a great guy for a couple of months. When we started dating, he told me that he is “sort of” bisexual, and that he’s hooked up with guys before. I was nonchalant when he told me, and I said I was fine with it, but I’m a little weirded out. I feel like he’s going to be checking out guys whenever we go out, or thinking my guy friends are hot. Am I overreacting?

A: Well, honestly, I do think you’re overreacting–but it comes down to personal preference and opinion, so if his sexuality is something you can’t deal with, then you’re not right for each other.

Before you start drafting your “it’s not you, it’s me” speech, hear me out. Let’s say he’s 100% straight as an arrow–you do realize that he would notice other women besides you, right? And as much as you may hate it, he would probably form some opinion on how hot your friends are, too (though if he knows what’s good for him, he’ll keep it to himself). So what’s the difference between him noticing other women or other men? He’s still choosing to be with you.

Is it possible that you’re a little worried about friends’ reactions? Since you’ve been with him for a couple of months I’m assuming it wasn’t a dealbreaker–you did continue to date him after all. I actually dated a bisexual guy a few years ago, and the experience was not much different than dating a straight guy–for me, hearing that he was bi was like hearing that he loves dogs or hates seafood. Some of my friends were a little bit shocked when they found out, so his sexuality was only an issue when I started feeling defensive about it. Read More »

Q: My sex drive is through the roof, and I can easily have sex twice a day, every day…but my boyfriend is a different story. He’s fine only having sex once or twice a week. We’ve been together for almost a year, but we’ve been fighting about this more and more lately, usually after he brushes me off if I’m trying to “seduce” him, at which point I usually make passive aggressive statements about how I should find someone who DOES want to have sex with me. I feel bad for saying it, but I’m also starting to believe it! Aren’t guys supposed to dream of having a girlfriend that wants to have sex all the time? What should I do?

A: I can sympathize–I’m also the sex fiend in my relationship, and it can be really frustrating. Here’s the thing, though — I don’t think twice weekly sex is really a problem, at least not in the way that once-every-3-months sex would be a problem. Seems to me that’s it’s just a preference and not indicative of how attractive and sexy he finds you. Only you know for yourself if it’s a dealbreaker or not.

I think a lot of the frustration might actually be coming from how the situation is handled, and less so the frequency of sex. Start by changing how you fight. I completely understand your passive-aggressive reaction (and I’ve so been there), but it’s only making him more defensive and not open to talking about it. Try bringing it up during a neutral time–not before, during, or after sex (or the rejection of sex)–and explain it to him in “I” statements: “I don’t feel good about myself when you brush off my advances.” Read More »