Three Questions: Should I date this older guy? and Dating my best friend’s boyfriend? and Will my boyfriend care about bumps on my butt?

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Dating Older Men

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Today we will be answering three short questions.

Question 1: 

Dear Guys,

I’m 15 and have been talking to a guy for awhile and we’ve both realized that we have romantic feelings for each other and that we would like to date. But he’s 18 so that’s not exactly possible yet.

He asked me to classify our relationship, so I said friends. This resulted in him saying that he felt like an idiot. Then he became depressed and distant for a few days. It’s clear that we can’t actually be together yet so I don’t know how else I would classify our relationship, or how to continue forward without getting overly involved for my age. How do I deal with the possibility of either of us getting involved with someone else and the jealousy involved in that?

Advice please?


Dear Amber,

Thanks for your question. It’s nice to see that you have a good head on your shoulders.

You’re right. The two of you should only be friends right now, until you’re of age. At that point a three year difference won’t be that big of a deal, although there’s still quite a divide between a freshman in college and a senior, but nothing like a freshman in high school and a senior in high school.

So what do you do until then?

What’s going to happen is—if he’s anything like the young guys around here—he’s going to start to pressure you subtly to start dating, or even to have a physical relationship with him. This doesn’t mean he’s not a good guy, it just means he’s a young man and he’s attracted to you. But this is not a good idea for you; if this does happen you need to set clear boundaries. Remember, guys aren’t so interested in being friends with women they would really rather date. Have you seen “Harry met Sally?” It’s an oldie but goodie, with a classic conversation at a restaurant about this topic.

We’d say the only thing you should do is keep in touch casually on Facebook, Twitter, or email. Just keep on each other’s radar. (We know that’s going to be hard.) But we wouldn’t get into phone calls, texting, etc. That’s going to be too intimate.

Believe us, even though he might start dating another girl, you’ll always be on his radar. We’re not saying he won’t fall in love with someone else in the meantime, but whenever he’s single again you’ll be the first person he thinks of.

Finally, we think you should do all the things a 15 year-old girl does now, and not wait around for this guy. However, if sometime down the road (years), the spark is still there, well then you’ll be better equipped to deal with an older guy.

Good luck,


ps. Please let your friends know about us. Thanks!

Question 2:

Dear Guys,

My BFF has a boyfriend named (anonymous). He is soo sweet and they have been dating a while. But he confessed his love for me today, but said he loves my BFF too.

To be honest I like him too. But I also don’t wanna hurt my friend’s feelings.



Dear Miranda,

Thanks for your question.

What do you do? You do nothing. Your best friend comes first. Even after they break up you should stay away from this guy. Otherwise you’ll be faced with a decision: Date this boy or have your best friend.

Also keep in mind that you’re young. And even if you decided to date this boy, it’s likely you’d break up soon after. Then you’d be left with neither this boy or you best friend.

Good luck,


ps. Please let your friends know about us. Thanks! 

pss. As per your other question: Progressing your relationship in a nonsexual way? That seems like a covert way of saying your boyfriend wants to by physical with you without actually defining it as sex.

Question 3: 

Hi Guys,

My guy really wants to do it doggie style, and so do I, but I have a bit of keratosis pilaris (bumps)  (for our readers) on my butt and I don’t really want him staring at that.

Do you think this is going to be a huge turn off for him or am I overreacting?


Cait xx

Dear Cait,

Thanks for your question. Let’s put it this way, we don’t know a lot of guys that would care.

Is your guy a sensitive person? Could you talk to him about this? (You don’t mention your age so we don’t have a sense of how serious your relationship is. We’re assuming you’re old enough to have sex and so you’re in a committed relationship.) Anyway, if he loves you he definitely won’t care. And believe us, if he’s been anticipating this for a while, a few bumps on your butt will be the last thing on his mind. In fact, during your session, his mind will be on hiatus anyway. (And his vision will be blurry.)

Hope this helps.

Good luck,


ps. Let your friends know about us. Thanks!

4 Comments on Three Questions: Should I date this older guy? and Dating my best friend’s boyfriend? and Will my boyfriend care about bumps on my butt?

  1. I am 22 and I am talking/dating a 28 year old. We been at the same stage for over a year. Everytime I ask him if he will ever ask me to be his girlfriend he always says soon soon. He told me from the start that he is a difficult guy. He is. For the past year he put up with so much of my crap and still suck around. So I assumed he likes me because if I was him I would have left a long time ago. I only met his roomate and he met my best friend. He always says soon u will met my brother but it hasn’t happened yet.  So my question is do u think he will ever ask me to be his girlfriend? Or am I just wasting my time? I really do like him.

  2. @LIza……It’s hard for us to say. Most of the time when guys stall like this it typically goes on and on until the woman finally gives up. But you’ve got to trust your gut on this one. Why don’t you give it a little more time since you really like him. But we wouldn’t wait forever. Feel free to check back with us in a bit.

  3. I met this guy through a girl I go to college with about 3 months ago they had known each other for several years and she was very into him. the three of us hung out several times and it seemed like when she would be all over he didn’t like it. after we all hung out the last time he asked her for my number and me and him started talking. he asked me if I wanted to come over to his place one night and he came and picked me up and we went to his place to watch a movie. when we were about halfway through the movie he leaned in closer to me and asked if I would be offended if he kissed me. I said no and leaned in to kiss him and in the heat of the moment we ended up having sex. I’ve had one FWB before and at first I thought that’s all he wanted but the sex is a little to passionate to be “just a thing” and when we “hang out” he always wants me to stay the night. The first couple times I stayed we didn’t cuddle much but now we do. confused by the situation I asked him “what are we?” and his reply was “idk I think we should get to know each other” I feel like he is a good fit for me because I can’t really be in a serious relationship right now because of work and school and he works all the time so we get a fair amount of space but I am starting to have feelings for him and I don’t know if he feels the same and it’s very confusing because I want to ask him but I don’t want to seem like I’m the nagging or clingy type and I don’t want to mess up whatever this is that we have so from a man’s perspective what does this seem like to you?

  4. @Bree……This seems like a convenient Booty Call. That might sound worse than we mean it. Just that, when you start a relationship by having sex it’s hard to know what it is. You kind of skipped building the foundation, and now that he’s getting regular sex from you, he’s going to want to keep doing that. However, he’s not necessarily going to want to add the relationship part to the equation.

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  1. Is he interested in friendship or something more? | The Guy's Perspective
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