Seducing a close friend who's interested but anxious

Help! This situation has gotten beyond frustration and should be so simple, easy, + wonderful, but...arrgggghhh!!

So: A longtime good male friend of mine and I are temporarily living together - the last 3 weeks and likely for most of the next month, too. We've had a history of flirtation, affection, etc. but have never crossed a line past making out, cuddling, and lots of touching. I've seen him naked; he's seen me partially naked.

He's never had a real partnership sort of relationship of any substantial length of time; sadly, mostly on/off again flings and booty calls. This is not my style - I'm more of a serial monogamist. He claims to want this, and in many ways has referred to me jokingly as "wifey" and has said I'm one of his closest friends, period, but we ultimately have NOT crossed a major sexual line.

We are NOT a couple; we never have been, but it can be confusing because we treat each other sweetly and have this flirtatious streak to our friendship. We share many intimate details of our lives together, but he has always made a conscious effort to minimize or avoid talking about his hook-ups and gets uncomfortable if it comes up. I'm pretty candid + open with him, though, about my own past situations.

It's like we've been dating, nonexclusively, minus a more sexual relationship. I'm an attractive gal - very slim, feminine, generally good-natured + happy. He's a bit overweight, but I find him so handsome + cute, and even hot sometimes.

Since I moved in early this month, the first week things were fun + flirty and seemed to be tentatively heading in a more sexually adventurous direction. But then he seemed to get anxious and backpedaled. When I gently asked about this lack of playfulness lately, he suggested he liked where things were and didn't want to ruin anything, etc. These excuses have come up before, but I'm not really buying it. The more I see him by living with him, there's a lot of anxiety there around multiple issues - work, health, public appearances, etc.

He is a single man and free to do as he pleases - I have said this openly to him. But I have also said it's hard for me to know how to behave with him because of the mixed signals.

I think the occasional hook-up girls are "safe" for him; minimal emotional involvement, no real commitment, not really integrated in his life, etc. But for my part, I feel like he backpedals on taking things to a more intimate sexual level because...? He feels anxious, or threatened, or scared? I told him I would never abandon him as a friend, but said I was curious to try for more. He tends to dismiss this as "oh probably not a good idea" and "I just don't know about this right now" but also says "but my buttons are easy to push" and "I've never lived with a woman before, I guess it's kind of exciting and new for me."

Sexually experienced, emotionally/relationship-wise, really wet behind the ears. I haven't been overly aggressive with him sexually, but I feel like maybe it's time to try a different tactic. ;-)

I'd like to try and feel like I have to take the lead, but we've nothing to lose and I can be happy regardless. But he seems to dwell on all the possible things that could go wrong instead of considering that the outcome could be lovely! (and ironically anxiety-quelling)

Ideas? Advice? I'm feeling braver and confident and am willing to try things to show him it could be really great after all, but I am sensitive to his feelings and care about him too...

Unless you are his therapist I would assume that his excuses are because he is not that into you especially given the roommate situation -he sees the benefit of keeping things stable as a roommate outweighs the benefit of getting involved with you. Many people are scared/hesitant about getting involved and they choose the other person over their fears or concerns. He is not. Respect that.

If you truly care for him...you will NOT take the lead. It will crash and burn and the ashes will be devastating.

Unless you are his therapist I would assume that his excuses are because he is not that into you especially given the roommate situation -he sees the benefit of keeping things stable as a roommate outweighs the benefit of getting involved with you. Many people are scared/hesitant about getting involved and they choose the other person over their fears or concerns. He is not. Respect that.

I used to think that, but he deliberately treats me differently than just a friend, yet he's not getting any sexual benefits out of it. He has admitted to feeling insecure, scared, and uncertain.

I definitely understand about stability re: current living situation, though. And I think he has always chosen to listen to his fears and go for "non-threatening" options.

It's just quite frustrating to have him kissing my stomach one night, and shying away the next. Argh!

If you truly care for him...you will NOT take the lead. It will crash and burn and the ashes will be devastating.

Can you please elaborate? I often feel that the more emotionally stable and less anxious person should lead a relationship...

He doesn't want a relationship with you!

He values the friendship and the flirting and the safety of knowing that there is a line.

If you pull him accross that line his level of anxiety and discomfort will cause him to emotionally withdraw and there will be no going back.

A relationship that crosses from friendship to sexual intimacy is rare and sacred...and should be a mutual and joint decision. Not a seduction by an aggressor.

Please stop "seducing" him. It is not up to you to "turn him around" towards a relationship that he doesn't want or is not ready for. You are living with him temporarily for whatever reason. Its awfully tacky and presumptious to try to jump him. Act like a roommate or ship out. Btw, he doesn't OWE you sex because you are living there or because you have seen him naked. If the roles were reversed and you were a man temporarily living with a woman, the voice of outrage could be even stronger around here.

Can you please elaborate? I often feel that the more emotionally stable and less anxious person should lead a relationship...

Two people should lead equally in a relationship. But THIS IS NOT A RELATIONSHIP. And because you are stating this, you feel he is unstable and needs to be fixed and so you have a right to do so. He may express feelings of fear and uncertainty not because he is a fearful person but is uneasy about getting into a relationship with YOU.

Some people say its good for a woman to pursue a little bit - to take the initial lead - but that means a woman sees a guy might be open to her advances and asks him out and after that, puts the ball in his court to see if he returns the interest, etc. Making the FIRST MOVE. it does NOT mean that a woman decides she knows better about what's right for the man and aggressively tries to get him in uncomfortable positions until he gives in.

Respect his choices, he's not up for playing house, nor is he into booty calls, imo.

Probably not the best idea to take the lead here.. He's said he doesn't want to cross that line so you should listen to him.. I've heard of lots of stories like this that have gone down hill very quickly once they started sleeping together.. It changes everything! You can act playfully, but remember the line. Respect his wishes, and maybe if and when he's ready to get more intimate then do so but only when that moment arises.. And even in that case, it will still change everything.

"I told him I would never abandon him as a friend, but said I was curious to try for more. He tends to dismiss this"

- I don't think you two should cross those lines.

Things would not be the same again 'friendship wise', if you do. ("I'd like to try and feel like I have to take the lead, but we've nothing to lose "- Yes, you do.)

AND, the fact you mentioned, you're more.. as you say "I'm more of a serial monogamist". Then by the looks of it, you two are not so compatible.

If you care about him, how about you start respecting him and his 'actions' of NOT advancing forward with you.

If you can't do this- them maybe you should move back out, if it's too much for you?

btw, "No means No" does not only apply to women. Get it?

I hear you guys, I do. And I don't want to push it. But he is also one who has invited me to take a shower with him, has kissed me and laughingly held me in sex positions while thrusting (uhh yup) and said there are "lingerie Sundays" in this household. Mixed signals, here! Sigh.

I'm not necessarily asking for a serious relationship. Just to have the door open for the sexual side of things to actually be explored instead of forever teased and talked about! So frustrating.

You have made it clear to him you are into manogamous relationships....and he is not.

Mixed signals is the nature of your relationship with him --- -sexual flirting without crossing the line. If he wanted to open the door, he would. He isn't.

And if you are frustrated --- then set clear boundaries. Stop playing games.

But most of all ---listen. He has said no as many ways as he knows how. He likes the game. You want to change the rules.

I think you moved in hoping he would cross the line. And he has not.

Have you guys ever passionately kissed? If your answer is no --- then his desire for you is faux.

Sound like the line is wherever you decide to let it bend. SO if there's showers and lingerie Sundays and kissing, let your monogamy take a month off and see where it goes just playing but not having sex. It may be a fun thing for both of you. And it may mean you get trapped in one of those "partner but not married" relationships as well.

Just remember how he treats women and sex in his life, they are a temporary fix and he sounds like he's quite happy playing the field like he does.

I believe it was an invitation to a shower....that never happened.

And "lingerie Sunday"....that never happened.

Just like the passionate kiss....that has never happened.

I believe the kisses have happened and all that it takes for lingerie Sunday to happen is for her to do it...

She just has to be honest with herself about what kind of relationship he is able to provide.

OP --- I just checked your back threads and this silly game has been going on for years.....your last post in March details your "chilling out" and him still being vague.

I think it is time to cut bait and move out.

That was March of last year. I drew a line last summer and said I didn't think he even knew what he was doing and his lack of close partnerships in his life up to this point was worrisome. I told him i couldn't be in his life til he got therapy but I'd be happy to help him look into it.

His father passed away very suddenly in December. I am close to his family and I reached out at that time out of sympathy and it was completely about his dad - no mention of anything between us or negative past events. He was grateful. There were very few friends of his own who showed up at the time.

He and I slowly re-established a connection this past spring and only in the last couple months have become close again. I don't think he's ever had a truly loving or emotionally as close relationship with another woman in his life. Realizing this I've been more open and patient with him this time. I'm frustrated by his anxiety/forwardness and back again but don't have extreme expectations. Just want to see how things might go from here on out with this in mind.

Oh - and kissing has definitely happened! He's very touch-affectionate and continues to be (cuddling, holding hands as falling asleep, etc). So... yeah.

And I'm happy to be off the monogamy train for a bit. In fact - I rather that be off the table to start with because I think it's too much pressure or expectation before trying anything in this case.

There's obviously some block if not just me then also in general. And I'm just really curious to figure it out!

Being curious about why someone is saying no to a relationship is about you and your ego, not about the other person's comfort level or interest in you. Why does he have to be subjected to your intrusive behavior to satisfy your curiosity if he's told you he's not up for it? Respect his wishes. (Especially if you don't want to be hunting for a new roommate any time soon).

If a woman stands in front of a single guy naked long enough and enough times, he may try to fool around with her. It does not make him want a relationship with you. It means that you are willing to lower your level of self respect to get some action that you will try to segue into a relationship. You are desperately trying to hook him. He has been clear that if you insist, he will touch you, but that doesn't make the contact meaningful or valuable. So you are willing to lower yourself to offer to parade around in lingerie or whatever sign of desperation - insisting that he really wants you. It is not your job to "cure" him of wanting to be single and fancy free. Also, I think your acts of sympathy when his dad died is something you put in the bank in hopes of emotional intimacy. Move out or stop this charade.

Whoa, whoa, whoa. Calm down. I would NOT feel good if I felt like I was forcing something... some of these comments are well-intentioned, and some could well be the case, but some are quite off base.

Thanks, everyone, though. I do appreciate it. Here's a bit more background + an update:

When we first met a few years ago, he'd made flirty comments and after some months, he did tell me he was interested in me and I was "so pretty...I want to be a better man for you... can't you kiss me just once?" This was after a big drunk escapade and at the time I was completely smitten with someone else, and I rejected his advances, saying as much.

So it's not like he never took initiative to express interest in me. I was just slow to come around and as I got to know him better, I liked him more and more.

Yesterday morning we both had woken up quite early, and I'd decided enough was enough and to really test the boundaries, beginning with giving him a backrub (this has happened many times between us, so no big deal) - but I slowly took it further. I decided that if he said, "no" or "stop" at any time, or anything to that effect, I'd stop immediately. But if he encouraged it or let me keep going...I was going to keep going...and ended up going down on him, which he enjoyed, but couldn't really believe it was happening. The worst thing he said was "Ahhh maybe this isn't a good idea," but that was about it.

He was laughing + smiling afterwards and seemed a bit in disbelief.. but then he hopped in the shower to get ready for work. When he got out, he walked up to me and gave me a big grin + a kiss. Hmmm.

I slept at a girl friend's place last night "to give you some space" but not sure what to expect this weekend.... Not sure if I should lean back more or continue to play with him...

I'm not sure what your post supports -that he let you give him oral sex? So what? It's obvious you don't care about him -you're just interested in "playing with him" as you put it and you want your own ego stroked if he "responds".

If you want to know how he feels about you then when you are completely dressed ask him if he wants to be in a relationship with you. And accept and respect his answer, whatever that may be.

what exactly are you looking for again....I am still unsure? a boy toy? hook ups..idk?