Setting Sail on the S.S. Dreamboat...

QUESTION: Dear Chuck and Garland,

 

I stumbled onto your website and after what I thought would be a quick glimpse, I found myself reading around for an hour! I love how real you both are and saw a lot of clarity in your answers. After looking for an entry similar to my situation and failing to find one, I decided to get brave and write in for advice.

I am a 29 yr old female who is 2 months into a relationship with a 33 year old man. We met through a friend and the story is sorta funny- I went on a blind date that turned out to be a dud and a girlfriend met me at after the date ended at a bar to debrief and laugh a bit. The guy I'm currently dating (lets call him Dreamboat) happened to be there too, works in the military with my friends husband, walked over to say hello and I caught his eye. He was on his way to a Bachelor party and our meeting was brief but the chemistry was like a punch in the face. He later got my number from his friend and asked me out 2 days later and we've been dating ever since.

 

Before I get to my question let me say this - I have the tendency to be a bit assertive. I know what I want and am not afraid to say it. I ended my last relationship because the guy I was dating didn't know what he future held. So I cut my losses and moved on. However with Dreamboat, I realized with his high profile military job that he is used to being in control, so I gave him the reigns form the get go. He plans the dates, picks me up and has southern hospitality (which I love!)

About me- I have never been married, have no kids, no baggage and am ready to settle down. These past 2 months I have let him be the "man". We share a ton of the same interests and just click. I am falling in love and think he could easily be a forever thing.

We see each other at least twice a week and I stay the night at his place(I always wait for him to invite me to stay). Our first date was hands off, however the second date I slept with him. It was the best sex I have ever had. Period. Fireworks every single time.

BUT, here's my issue. He is divorced and has 2 sons under the age of 8. I have never dated a man with children OR one who has an ex wife. He told me that he only married this woman because she "got pregnant" and because of how he was raised, it was the right thing to do. After a hellish first year of marriage he planned on divorcing her but, BAM, pregnant again. So he stayed as to not leave her with a 2 year old and newborn. Then, after coming home from his 3rd deployment he divorced her.

Now, he sees his kids every weekend. That's his time slot. I have met the boys and we have done a number of fun things together. They are great kids and coming from a large family myself, I am a natural nurturer and adore them. They are not my worry.

He deploys in 4 weeks and I don't know how to have the "us" conversation or if I should even be the one to bring it up. I am a smart, ambitious good looking girl and I feel like he should be the one to make sure to secure things - like it's his duty if he cares. We have never discussed the "what are we" sort of thing either. I have met his brother, his friends and he takes me to all sorts of functions but we have never had the exclusivity talk. At one of the events he introduced me as his "girlfriend" and my jaw almost dropped. But since then, the subject has not come up. I assume he is not seeing anyone else (between the kids on the weekend and his demanding job I don't know when he would have the time). But I am curious about how he feels about me. What he wants at this point in his life... more children (because I want some of my own) or to be married again (because that is what I want. I am worried that because he is newly divorced (2 years) he may not want to marry for a while. I am assuming all of this, really want to know but am afraid to bring it up and ruin things. Even though I am ready to have that.

It would make me so happy to start a family and I see that all with him.

Lastly, he deploys in 6 weeks. For 8 months. I want to know where we stand before he goes. Sort of like, now, so I can cut my losses if he thinks this is just a casual thing before he does. I wonder if I should be the one to bring this up - the whole what are we, I will wait for you, I care about you... or if that's "his" job to ask. I don't want to look desperate or scare him away. I don't know which direction to take. I am totally analytical and like most women,I want to have the security of knowing the person I am investing time with feels the same.

I would love your insight. I don't want to say something too soon, out of impatience and mess this whole thing up. I also understand that men like "the chase" and need to do things on their own terms. Thanks, hope to hear from you soon!

 

GARLAND: Great question! And thanks for stopping at our blog, enjoying it and asking for our humble advice. I hope we can shed some positive light on things!

 

I like the way you present the facts and I really feel like your take on things.

 

Two months of dating is a pretty short period of time for a lot of people and I'd typically lay a bunch of short-time related 'cautions' around my reply, but I get a feeling that that's probably not needed for you. So, I'll cut to the chase  - Ask him what he's feeling for the long term expectations in your relationship.  You've given him a lot of say in your relationship, a lot of control in the direction things are going - the planning, the movement and the flow, but that sounds like it would get old very fast for a woman like you. It's probably easy for you to give a decent guy the rope and let him swing from it or hang from it based on his own decesions - but only for a while. I think you should take some of the control and flow from him and sit down and feel him out, this is your life after all, but you don't need me to tell you that.

 

I think it would be fine and reasonable to ask him what he expects while he's gone and when he returns.  Honestly, I think the time apart would give you both a good chance to catch your breath and see how things work when you are forced to be out of each others presence. I encourage you to be optimistic in his absence and not feel like you have to force an answer out of him BEFORE he leaves. By the way, don't toss marriage and kids up on the table right now and make him feel like his feet are to the fire - with him going to what could be a dangerous spot somewhere in the world, you need him relaxed and focused on his job and staying alive.  However, let him know how much he means to you and let him know that you want him in your future, and be comfortable in giving him some time to put his feelings together, even if it means answering you in the first few weeks of his deployment. You won't look desperate and you won't scare him off - at least not by asking!  Sometimes a long flight and some nights with free time will make a man understand where his priorities are. 

 

Best of luck in a positive outcome!

 

CHUCK's answer may follow in a few days. 

The Thought That Counts

A question for the brothers:

Michael and I had been dating exclusively for 10 months when Valentine's Day rolled around. For my birthday in October, he gave me a laptop computer; at Christmas, he gave me a 42" plasma TV (that was actually for his pleasure, I told him I didn't want a TV). We were talking after I got off work on Valentine's Day when he asked if I had received anything at work. When I said no, he indicated that he had spent $150 for some flowers. The next day, after "following up", he said he had sent the flowers to the wrong address. Now, here's the rub. He never said another word about it after that. Not "I'm sorry sweetie", not "I'll make it up to you", heck, he never even wished me a happy VD. I believe he was lying about sending the flowers. What do you think accounts for his behavior?

GARLAND: Thanks for your question.

It's been over a month and you are still angry because Michael hasn't wished you a happy Valentine's Day. Let me just tell you, in my opinion, that there is no "behavior" to account for. By your own admission, he bought you a laptop (about $800) and he bought you a 42 inch plasma (about $950) on the other requisite holidays, and when you don't get some flowers on Valetine's, suddenly in your eyes, your boyfriend is trippin'.

Chuck and I do our best not to "side" with anyone when we answer questions, and I'm not "siding" with your boyfriend, but I am going to call this just how I see it: More than likely, your boyfriend isn't lying or playing games or anything else sinister. His $150 flowers never made it to you and he's probably pissed off to the highest of pisstivity. Even saying the term "Happy Valentine's Day" probably rubs his nerves raw. So you may want to stop waiting for that to happen. You're boyfriend is probably still trying like hell to get that $150 put back in his bank account, and he will probably never see that money again, and you're mad that he didn't wish you a "Happy Fake-holiday-commercially-driven-dump-guilt-on-husbands-and-boyfriends-and-give-me-jewelry-tines Day"

A little tip when it comes to men and dating in general - past performance is the best indicator of future performance. If your man has 30 or 40 ex-girlfriends, chances are good that you'll be an ex very soon, If your man lies to you early on, chances are good that he'll lie to you more in the future, if your man buys you expensive gifts on holidays, chances are he'll do it more often. So, based on what YOU said, I can't figure out where all this doubt is coming from. You even put 'following up' in quotes to clearly indicate that you don't believe what he said. If you are this quick to toss your man under the bus when you don't get flowers on the busiest flower day of the year and suddenly now your man has no credibility - you are going to be miserable in this relationship.

Let me share just one bit of insight here. To you, you didn't get another gift or some kind words to your satisfaction. He tried to do something nice for you and may have lost $150 in the process - I guarantee that that florist is giving him a hard time when it comes to getting his money back. So right now, the last thing your boyfriend is thinking about is saying, "Happy Valetine's Day Sweetie!" He is thinking about his $150!

Do you know how men see 150 dollars? Like this:

• A pair of LeBron James' Nike shoes


• 2 custom made dress shirts


• 7 brand new DVD movies


• A month's worth of gas


• 5 new pairs of cufflinks


• A pair of Hugo Boss dress shoes


• 3 new Xbox 360 games


• 2 good lapdances (with tip)


• 6 bad lapdances (with tip)


• A whole night of poker at a casino


• 4 very nice silk ties


• A real nice DVD player


• A pair of jeans and a Barry Sanders throwback jersey


• 5 retro baseball caps


• A detailed cleaning of his truck...

Okay, okay - let me stop here. My point is this - I think you're making a little bit too much of this. Your man is pissed off that he didn't get the flowers to you, he thinks he looks bad in your eyes [which he clearly does] and he'd really rather put the whole pseudo-holiday behind him. If this really bothers you though, chances are, you are going to find plenty of reasons [small as they may be] to be angry at him in the future. I say, for the sake of the women that are looking for a good guy - cut Mike loose and move on. Someone else will be happy with his laptops and TV's and good intentions. Either that - or find it in your heart to enjoy a guy that 'seems' to be doing the right thing.

CHUCK: Okay, Garland let you have it. And I'm... gonna let you have it. No, just kidding. But I do agree with most of what he said. About the six bad lapdances, I can only guess.

Let's see: $150 worth of flowers, delivered to the incorrect address that Michael provided. If those flowers were delivered, the chance that he could recover a full refund for those flowers is pretty slim.Whoops. Do I think it's a little strange that he didn't mention it again, even just to bitch about the florist's inflexible refund policy? I guess. Do I find it rude that he never said "Happy Valentine's," to you? Again, I guess, but given the colliding factors of frustration and embarrassment involved here, I can see it happening. Do I believe that it's unusual that you're still obsessing over this? Pretty much.

Let's examine your reaction for a minute. Has Michael ever given you cause to doubt his veracity? You haven't said. So why the knee-jerk jump to distrust? There's a possibility that he might have fabricated the flower story. Because, let's face it: the pressure is on men to "put out" on Valentine's Day. By that, I mean, prove their affection with money. And you were obviously looking for something attention-getting.Maybe he didn't want to disappoint you by saying that he couldn't afford a big gift, or he'd overspent on the past gifts he got you. So he made up this story, and disappointed you anyway.

Either way, since this is apparently bothering you, meet the issue head on. Ask him, "So what ever happened with those flowers." Gauge from his response whether he's telling the truth. But before you do that, think about how important this whole issue is to you. I understand, if he lies to you about this, what else will he lie about in the future? But this seems like a clear case to me of looking for problems where there might not be any.

Virgin Territory

QUESTION: Hi Guys,

First thank you for the site. It's been helpful and interesting hearing your advice. If you have time to answer my question I'd appreciate it. (sorry it's long!)

At what point should a girl let a guy know her wishes regarding sex?

Some background on me: I'm 29 and a virgin. I was raised in a fairly strict Christian and didn't really date until I got to college. I had a serious boyfriend for quite a while where the abstinence thing was okay, he was as religious as I was. Eventually we broke up and I was heartbroken for quite a while. I casually dated after that and focused on my career. Now at 29 I find myself wanting to seriously date and have a long term relationship, maybe even eventually get married. I'm now far more stable, emotionally and financially ready for a serious relationship than I was in my early 20's.

I'm not necessarily stuck on abstinence now, but I'm not going to have sex casually. Ideally I'd like to date someone and develop a relationship with them for several months before we take our physical intimacy to the next level. Reading a question/answer from another one of your posts, I agree with not explaining my preferences regarding sex on a first date, but I'd like to have a good idea of what point I should be letting a guy know? If things go well and he wants to see me again should I be telling him by date number 3 or date 5....?

I don't want to lead anyone on, but then again this is not something I want to compromise on. Considering how some of my friends who aren't necessarily sluts are giving up booty within a couple dates, I'm rather at a loss on how to when/how to express my wishes regarding sex without coming across as a prude, weirdo or some kind of 'challenge'. Nor do I want to scare a guy off because virgin at 29 screams commitment.

Any suggestions on how/when I should be having this talk? Thank you for your help! :)

C

GARLAND: Thanks for your question and thanks for checking out our blog! Hopefully we can give you some good insight and advice.

I think, as a woman, you've got all of the sexual intimacy cards stacked in your favor - so you REALLY call all of the shots! Any time and place you want can be met with a few simple words.

Now, for ME - when I was single, I never really pressed a woman for sex, and I don't think any guy should. It usually happened when it was meant to happen, sometimes after a few dates sometimes after A LOT of dates. I think for guys, if sex is all they want, by our nature we're only going to hang around for 3 or 4 dates. But, if a guy is still interested AND excited about spending time with you and he's still calling and taking you out after 7 or 8 dates, I think that's a good sign that he's about MORE that just 'gettin' some.'

Now, keep in mind that these are MY numbers. And they may not be the norm. But, considering that you have stuck to your guns and maintained something very unique and special for 29 years - move slowly towards giving it up. Make sure that the guy you choose doesn't make you feel rushed or pressured to sleep with him. Don't be afraid to talk to him about your being a virgin - HE SHOULD, ABOVE ALL - make you feel special and respected - and this is not exclusive to virgins! All men should make the women who share their intimacy with them, feel special. But TALK to him about it if you consider HIM to possibly be The One - listen to him and try to gauge his true thoughts about it. Sadly - a lot of guys find a dark thrill and challenge when an opportunity with a virgin comes along. If he focuses more on you The Woman and less on your body The Virgin, then the time may be right. Trust me, all you have to do is tell him [face to face, or over the phone, or in a letter, or in an E-Mail...] that you want to be with him and let him know when and where and he'll be there.

Be smart... BE SAFE!!!!!!!

Good luck on your decision and thanks again for such a special question!

CHUCK: C, my dear friend, I have news for you. Whenever virtually any woman, anywhere, is ready to have sex, she can have it. The quality of that sex may not be what she hoped it would be, but sex can be had. While womens' pay may lag behind mens', and they may be under-represented in Congress, that is one advantage that women retain: the Right to Say Yes.

Seriously, though, there is a standard that I stuck to when I was single, and I believe it still applies, even to virgins. It goes like this: After three dates, a man or woman knows whether or not they want to be intimate with the person they're dating. Some people call that the Three-Date Rule. I just call it common sense. It doesn't necessarily mean that on Date #4, clothes will be ripped off... but by that time, a person knows whether they want to pursue a deeper relationship. Whether things progress further after Date #3 is up to you.

Like I believe we've said before, there is nothing wrong with sticking to your guns, in terms of not rushing into ridding yourself of your virginity. You've kept it this long, so there's no reason to lose it to the first bum you encounter. But you know that already. By the same token, I think it puts men off when women present that kind of information as if it were a dare or a challenge: "I'm a virgin at 29. Bet you don't wanna go out with me now! Do ya?"

Once you start seeing someone, you should make your views known when the subject comes up. Let him know that intimacy isn't completely off of the table, even though you're not rushing into it. You seem to be very good at expressing yourself. I don't think you'll have a problem. Thanks for the question.