“I am 18, and a bit of a loner. I have never been in a relationship of any kind, and I’d just like to ask how the entire process works.  I have girl friends, of course, but it’s the all important space between the words. As a bit of background, I am a geek, smart, but socially inept. I have no idea what to say to people, and thus never make the first move in any way. If someone else starts a conversation with me, I can generally muddle along, but I am forever second guessing myself. I would not say that I lack confidence, but I tend to be very self-conscious, especially about what others think of me, not so much my appearance. For example, this is the third rewrite of this question I’ve done, because I am often considered to be arrogant, and I am really trying hard to remedy this. At this point, I’m not even sure I have a question, or whether I just need to tell someone how insecure I’m feeling. “

It sounds like maybe what you need is just more experience with people; this will make it easier for you to get a handle on the complicated ways that people relate to one another. Also, the more you spend time with people, the easier it will become for you and you’ll grow to be more confident/comfortable. Confidence is important because it’s something that other people pick up on, especially the women you might want to date.

In fact, sometimes even pretending that you are confident/comfortable in a situation can make you feel more confident. Act relaxed and you’ll feel more relaxed, etc.  As they say “fake it ’till you make it”.

Also, don’t worry about all the girls that are your friends: friends who are girls often have other friends who are also girls and they may be happy to introduce these friends to you as romantic prospects. ^_^

You say you’re very busy in your life, so I think it might be good for you to take some time to relax and plan some outings with friends – go with them to a party once in a while. It will give you the opportunity to watch how other people interact and will give you the chance to meet some new people and practice becoming more comfortable interacting with people.

You could even plan to go see movies with friends – this kind of outing is great if you’re worried about having something to say to other people, because you can just talk about the movie.  ^_^

Relationships can be built many different ways.  Some people end up in romantic relationships with people they started out being friends with; this offers the advantage of being involved with someone who you already know you get along with and with whom you have things in common.   Other people end up in romantic relationships more spontaneously, perhaps after a blind date or after meeting when out with mutual friends.

You never know how you’re going to meet a romantic partner, so they key is to be open to seeing it and make a move when you think they might be interested.

I hope this helps!

Going for drinks after a show is a great idea because it automatically gives you a topic for small talk

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“My boyfriend and me were able to cum at the same time for the first time yesterday. I really liked it but it has never happened before. In order for me to cum I have to have intense stimulation of my clit so I used a electric toothbrush on my clit while i am in the cowgirl position facing him. I want to be able to have us cum at the same time again so I was wondering if you had any tips for me on how to make it so we can cum at the same time again.

Also I had always wanted to have a threesome. I have never had a boyfriend completely agree with it before until my boyfriend now. He only said it needs to be someone we trust. I always wanted to but now that i have a chance to I dont know if i actualy want to I feel really jealous even thinking about him doing something to another girl and i feel kinda weird about thinking about another guy doing stuff to me because I love my boyfriend so much. So im torn between the fact that I really want to try it and and the fact that I feel very jealous and weird about it. I was hoping you would have some advice for me about it. “

Congrats on being able to come at the same time while you two were having sex – that’s always a pretty cool experience!  It sounds like what you might want to invest in is some sort of hands-free clit stim that you can use while you’re having sex.  Something like THIS or THIS or THESE might do the trick so that you don’t have to worry about holding a vibe against your clit while you’re trying to have sex and should open up a few more position options for you as well.

As for the threesome idea, it sounds like this might not be something you want to try right now in your relationship.  I’m sure there will be other times in your life where you’ll have a chance to try it out, but if you feel at all like it would make you jealous to see your boyfriend having sex with another woman, then I don’t think you should do it.   It’s not worth risking your relationship just for one night’s experience.

I think reading this post might help you as well: https://thesspot.org/2008/03/reader-question-introducing-a-threesome/ (make sure you also click the hot links to other related posts).  A threesome might be a fun fantasy that you two could play with using your imaginations (or a blow up doll, I’ve tried that and it was kinda fun/funny), but, to me, it sounds like you shouldn’t make it a reality right now.

A threesome may be something you two could try later on, or maybe you’ll decide that this is something that should just stay a fantasy – but it’s better not to rush into something that you might not be ready for emotionally.

I hope that helps!

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This post, Coming Together and Maybe not With Others, originally appeared on the s spot on May 21, 2010. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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“Dear Shay,
Before I start, wanted to say that I love your column. Its a great source thats entertaining and informative. Now onto the crux of the issue. I have a friend whom I met at college. One night we were hanging out and (after too many shots of whiskey) we start making out on the couch. The next day I felt that because we were too far apart in age (she’s 7 years older) and because I wasn’t ready for an emotional or physical relationship at that time, that I should not continue to see her in a romantic way. I told the next time I saw her and she agreed that we shouldn’t be dating but that we should continue to be friends.
Now, several weeks after that event has occured, she messages me every day now with how her day is going and that she wants to hang (again all the time). Also whenever I do see her she flirts with me more and more, such as touching my shoulders, my neck, and kissing my cheek. I’m fine being her friend and hanging out with her but is there any way to make her see that I don’t want to be anything more? I feel that she wants more than i’m willing to give but I don’t want to hurt her or make her feel embarrassed.
What is a little worse is that now there is a girl in my class that I really do want to ask out but I don’t because it might hurt my friends feelings. I believe she hasn’t had many bf’s before this and me rejecting her after kissing her would hurt her self esteem. What are your thoughts on this and is there any way to continue a new relationship without hurting my friend?“

It sucks when things get out of hand and you do something that you know you shouldn’t with a friend.  Crossing boundaries can be wonderful, but it can also be problematic and it affects people in different ways.

Since you’ve already talked to her about staying friends but not going any further romantically, I think you should try ignoring her advances (for now) and continue to treat her like a friend.  I text my friends all the time and I like to hang out with my friends – however, I don’t (usually) rub my friends’ shoulders and necks or try to kiss them on the cheek.  And this is the behaviour that seems to be the main problem because it shows that she feels a little more than friendly towards you.  Since you don’t want to hurt her feelings, you’re going to have to be subtle – you’re also going to have to accept that whatever you do, you probably are going to hurt her feelings,  at least a little.

Talk to her about this girl that you’re interested in, ask her for advice, remind her how glad you are to have her as a friend. These are subtle ways to hint that you care about her, but that your feelings towards her are platonic.  This will also let her know, gently, that you are interested in another woman.

If she doesn’t seem to take the hint, then you’ll have to talk to her about how you’re not interested in her in that way. It may end your friendship, but hopefully not forever.

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This post, Crossing Boundaries with Friends and then Trying to go Back, originally appeared on the s spot on November 23, 2009. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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“I have three questions. I’ll be straight and to the point, then provide background. Alright? Here goes.  My boyfriend is a little dense when it comes to sexual things, what’s the best way to go about teaching him?  And two, do scratches in the va-goo heal quickly, or would they easily be infected?  And the last, but most perplexing. How does one go about sexing when the two persons are different size catagories.  (i.e. Fluffy large framed femme and medium fairly built male.)“

For your first question, I guess the best advice I can give you is for you to just tell him what you like.

I get that sometimes this seems tricky because people don’t want to seem bossy or overly demanding in bed, but there are subtle ways to do this. A lot of guys (esp the ones who care about how their partner is enjoying themselves) pay close attention to their partner’s reactions – what kind of things make them moan, gasp, or pull away.

So give him lots of positive reinforcement (moaning, telling him “that’s the spot”, etc) when he does stuff that you like. When he does stuff that you don’t like, or isn’t quite hitting the mark, try just gently grabbing his hand or body and shifting him/you until things are where and how you like them.

Another thing you can try is watching a little porn together. While you’re watching, point out things to him that you think might be fun to try or that you think might feel good – “ooh I bet that feels nice, do you want to try that?”

Next, vaginal scratches – yeah, if possible avoid having anything scratchy go anywhere near your vagina. He should be keeping his nails short (and clean!) if he wants his fingers inside you. Little surface scratches like that should heal fairly quickly, but look out for any soreness or swelling that lasts more than a day or two.

And finally, managing size differences – it’s not difficult usually, there are a number of positions where size doesn’t matter much – like any position where he’s entering you from behind (doggy style, spooning, etc). Try sitting on your desk while he stands between your thighs – that way you can face each other and he can fondle you, etc, while you have sex without either of you having to be on top of the other. (Pssst: this is also a great position for dealing with high differences!)

Good luck!

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This post, Getting What You Want In Bed, originally appeared on the s spot on November 6, 2009. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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“Hi, Shay. this is alil off from ur ussal questions. But ur the only person i thot would have an idea. About a year ago. I tried internet dating. Past relationships hadn’t worked out. Due to my faults or theirs.Anyway. Me and my gf met on a site. started talking n such. Finaly decided to try dating with eachother over the internet. Even though there has been no physical activities. basicly the questions ur used to. We have shared alot of mental bonding to replace the physical. now for my problem. a few days ago. she told me she had lost her all attraction to me. But she’s still in love with me just the way she was before she lost it. Now I would think this would be a big problem for our futer. and were getting close to the time were going to meet. (safly ofc) and if shes not attracted to me. i dun think shes rly gonna wanna be going on a date with me, love me or not. So what my question here is. Do you have any idea’s on what we can do to revive her past attration to me. I’m already trying to re-arange my looks abit. We have had a happy relationship together and I realy wanna try to fix it in any possible way I can.“

It sounds like you’ve fallen into her “friend zone” – that is, she thinks of you more as a friend than as a lover. It’s the whole “I love you, but I’m not IN love with you” thing. We like to categorize the people in our lives in a number of different ways: school friends, work friends, and childhood friends; immediate family and extended family; friends and more-than-friends.
Once you’re in someone’s friend zone, it’s pretty hard to bust out of it – it can happen but it usually takes exceptional circumstances which are, like I said, exceptional and unusual. I don’t think re-arranging your looks is going to help re-kindle the romantic attraction you’re hoping for; so if you’re working on your appearance, I hope you’re doing it more for yourself than for her.

My advice is to enjoy having her as a friend and confidant, I’m sure you’ve shared quite a lot in your time chatting online together and it would be a shame to throw all that away. However, I don’t think you should press the romance issue any further with her, maybe she’ll change her mind, maybe she won’t, but that’s up to her and not you.

Good luck!

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This post, Yes, Friend Zones Exist Online, originally appeared on the s spot on October 29, 2009. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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Hmm that’s an interesting predicament.
A lot of people do tend to go through a sort of “wild” phase at some point in their life, where they want to have fun and experience new things (i.e. party hard and have lots of sex). Of course there’s always a lot of variability, and not everyone is looking for a string of one night stands at the same time. It shouldn’t be too hard to find some women who are interested in an actual relationship.

Sometimes what can really have an effect on the tone of your encounters is the context and this might be what’s tripping you up.  If you’re looking for your next potential girl friend in bars and clubs, you might not find the type of girl you want.

Look for girls in the areas you have an interest in: if you’re into fitness, try picking up some girls at the gym; if you’re into gaming, see if there is anyone cute in the gaming club (they DO exist!). Also, try talking to girls in your courses, the ones who are showing up to the same lecture as you already have at least two things in common with you! (i.e. they are taking that course AND actually showing up to lecture)

I know it can be rough, but consider not sleeping with girls on the 1st “date”; try to hold out a little longer so you two can actually get to know each other a little and start to form a relationship.

In conclusion: start picking up sober chicks instead of drunk ones; find girls with common interests; and make it known before you bed her that you’re interested in something more.

You might end up having less sex in the short-run, but hopefully a more fullfilling relationship in the long run. :)

I hope that helps!

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This post, Looking for More than Casual Sex, originally appeared on the s spot on October 23, 2009. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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Since Julie is such a good friend of yours, I think it would be nice for you to ask her if it’s alright with her for you to get involved with Troy. Obviously you’re only asking to be polite (and so that she hears about it from you first), since it’s not up to her who you’re allowed to fall in love with – but it’s still a considerate thing to do for your friend and it will probably put your mind/guilt at ease. Besides, if might be good to know how she feels about you dating him, and maybe she’ll even have some useful advice.

As for John, ex boyfriends aren’t allowed to decide when and who their exes get involved with. If Troy is John’s best friend though, it would be kind for him to talk to John about him getting involved with you; like I suggested you talk to Julie.

Some people have a really hard time finding people that they can connect with romantically, so I don’t think you should waste this opportunity because you’re worried about your friends; if they are true friends they will get over it, even if they do have a problem with it at first.

I hope that helps!

*names have been changed

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This post, Dating Friends and Friends of Friends, originally appeared on the s spot on August 10, 2009. If you are viewing it anywhere other than in a feed reader, it was scraped illegally and without my permission. Please email the(dot)s(dot)spot(at)gmail(dot)com and let me know.
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