First Date DC

Selkie writes,

I’m a nearly 30 year old never married female interested in relocating from NYC area to DC vicinity. I was in a long term relationship for the last 5 years on and off. I’m looking for a fresh start and a change of scene. Hence interested in possibly moving to DC. My question is whether I’d be fairly sought after by eligible men in DC. That sounds terribly cold blooded & mercenary doesn’t it?

Here are my plus points:

• Former model (just print/commercial, not high fashion)
• Poster child for Blond Waspiness.
• Still thin, healthy living, not much wear & tear. (Stayed out of the sun, don’t smoke, rarely drink, imbibing caffeine is my only vice)
• I like men and don’t feel bitter towards them.
• In fact I often put myself in their shoes and have empathy.
• I love being a woman. I also like being a tomboy.
• Which means I like being a girly girl, but can also be down to earth & get dirty. (Not that kind of dirty, I meant mud )

Now for my possible negatives:

• I’m not on high powered, high paying career path. I have a small graphic business and am debt free with about 200k in investments.
• But I am more interested in being a fairly traditional loving wife/mother then juggling job/home/family.
• I’m not formally educated. Opted to model instead of head to University. When I was done modeling, instead of going back to school, I had to take care of my mother who had a stroke.
• I am an avid learner on my own and don’t feel particularly inferior by my lack of a higher degree. Don’t know if multi degreed men in DC would feel the same way.
• Lastly, I’m a political orphan. I lean right, but have a few liberal tendencies. Does that drive men nuts ?

So do tell. Am I appealing on paper to men in the DC area? Or am I bit too offbeat from the typical DC chick? All advice appreciated.

DCB says,

Are you kidding? You’d be like a dead fish in a sea of sharks. DC is so ugly the 7’s can pick and choose: if you are thin and have a decent face, you will be treated like a supermodel. You will get so much attention that in a year you will turn into a total bitch. But unless you send me a picture, it is hard to be absolutely certain…

Kathryn says,

Wow. Just…yeah. So. Here’s what I think: there are tons of douchebags in DC, and they’re all going to LOVE you.

Please make sure you look for your mate exclusively at Smith Point, City Tavern Club, Gold Cup (Members Hill only, fall and spring), Town Hall, Third Edition, and Local 16 on weekends. Actually, you should probably go ahead and sign up for Late Night Shots now. Get to know your crowd/scene before you even get here. If you need a membership, just let me know.

male dcbachelor reader writes,

Okay here’s this situation and I’m not sure how to proceed.

So on sunday afternoon I was at the bar with a large group of friends and friends-of-friends. We’re drinking beer, eating nachos, watching the football games, and having a good time. I was chatting with this girl for a good 20 minutes. And when she goes to the bathroom, her friend tells me that she has a boyfriend. I said nothing, just smiled and nodded.

So the girl comes back, and we chat a little more. We’re watching the football games and at the time when the Eagles fumbled and the Giants recovered for a touchdown, and basically got back in the game. She whooped and cheered, and goes “I hope the Giants win!” so I was like, “so how did you get to be a Giants fan?” She goes, “I grew up in NYC and moved here a few years ago.” At this point, I decided to test whether she really has a boyfriend or not. I go “if your boyfriend is an Eagles fan, I don’t know how you guys get along during the football season!”

She says: “Oh, I don’t have a boyfriend. Well, we’re dating, but it’s not serious. He’s not here in this town.” I took that as a green light, and a few minutes later we exchanged contact info, saying we’d get together for coffee.

Looking back on it, the way she downplayed the boyfriend bothers me a little bit. I haven’t called her yet, and I’m not sure if I should. I probably will anyway, just to feel things out. What do you people make of this? Is she really taken but just wants hookup action on the side, or is she about to dump the other guy (whom I don’t think lives in DC from what she said)? I don’t intend to be one of those suckers who get only half the attention from a two-timer.

DCB says,

What the fuck is your problem? Why do you care if she has a boyfriend or not? Your “if your boyfriend” line was just lame: it’s like you were searching for approval to hit on her.

Don’t call her; you don’t deserve to bang a girl that is basically begging to get banged. I’ll take a guess that you are one of those traditional guys that doesn’t feel “right” about hooking up with a girl that may be hooking up with another guy. Good luck with that, and welcome to the 21st century.

Kathryn says,

Never, ever listen to the girl friend. Especially if you’ve never met them before and you don’t know their dynamic. From what you’ve said, it seems you were obviously digging Girl, and Friend noticed it. She waited until Girl was in the bathroom to tell you she has a boyfriend instead of, say, mentioning the boyfriend to Girl in front of you. And to me, that means Friend has a bit of a jealousy problem. She probably thinks it’s “not fair” that Girl gets all the attention, and she’s already dating someone! Friend sounds like a miserable little green-eyed cockblocker. Not that I have ever known anyone like that.

In the future, let Girl give you the signals. Ignore the Friend on topics like this. If Girl is interested, she’ll let you know.

Bumptious Bungler writes,

Hey guys,

I was the guy who wrote in a while back about the girl at the strings concert who was “waiting for her date.” The advice you gave was so fun I figured I would throw this situation by you: Have first-date drinks after work with a lovely girl. It’s pretty nice. Not mind-blowingly spectacular, but not horrible either. Got a cheek-kiss greeting, so I’m prepared for a cheek-kiss goodbye. No biggie; I’m pretty confident I’m getting a second date.

I metro to work, but she drives, so she was kind enough to drop me off at my place. Problem is that when the time for the kiss comes I reach out to touch her shoulder/arm. Do I reach that? Oh no, dumbass touches her boob. Not a “grope” per se, but definitely a covering/cupping type touch that lasts as long as it takes to cheek-kiss and pull back.

So what do you do in that situation? Laugh it off? Profess you are sorry? Say you usually don’t go so far on a first date? In my case I said “Have a great weekend!” and left. Sent a text message 10 minutes later saying I totally meant to touch her arm, and that if we did dinner it better be really good to compensate. So now she either thinks I’m a total grope-fiend, or a neurotic freak. I accept that I could have handled that better, but do you have any suggestions how? (Not that I plan to accidentally boobie-touch again anytime soon…)

Kathryn says,

Always good to hear from those we’ve helped in the past, even if it just made you laugh at your own problem.

And let me tell you, I’m laughing about this problem. I really don’t think she thinks you’re a groping fiend. You didn’t move your hand in any way that could have been considered a caress or a grope, did you? If not, she probably found your shock/surprise kind of cute and charming. I think texting immediately was actually a decent recovery. But since you asked, you could have said anything that suited your sense of humor, from “well, now, that’s not an arm, is it?” to “ah, did I just touch what I think I touched? oops…” to “sweet. Now we’ve been to second base.” Anything that conveys you did it accidentally, you’re confident enough not to let it freak you out, and you can laugh it right off will work just fine.

Then, just for the record: a cheek kiss is not necessarily an indication of any kind of desire (or lack thereof, in your situation). I recently became part of a social circle where everyone does the cheek kiss hello and goodbye. I’d never seen so much cheek kissing until a few months ago. But I can assure you it’s quite automatic. And I know people who cheek kiss hello on a first date could quite easily do some real kissing at the goodbye. Just sayin’.

DCB says,

“Oops sorry that was my evil twin,” or something similar. And then never mention it again. You made a big deal out of it when you shouldn’t have.

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aw writes,

Hi guys (30 year old male)

Why am I writing you? Well, I suppose you’ll have some snarky response that I can’t wait to hear.

I guess i have a tendency to focus more on the emotional connection than the physical connection. That being said, I tend to be a little more on the cautious side when meeting new people. I tend to be kind of protective of myself until i have at least ascertained that the person is being somewhat honest. I’m not very good at the nonverbal communication either - I tend to be more verbal and straightforward. I don’t simply have the mindframe for a lot of the ‘pretend you’re busy’ or ‘make them wait for you call’ or something like that. If I like someone, then I call them.

I guess the question is how can one tell after only 2 dates that they’re not interested. I mean, clearly there was enough interest after 1 date to try for a second, so…. what happened? And it’s a recurring theme.

Are people so jaded by other people not being honest or trying for the quick score that they assume everyone else is? I mean, I like to believe that most people are basically good and I treat people with respect…. but there’s something I’m just not getting.

DCB says,

Here’s what you said in your question:

1. “I’m a beta male with no game.”

2. “I don’t understand how attraction works.”

3. “I bore my dates to death.”

4. “Girls use me for free dinners.”

5. “I am losing the game of life.”

Who cares if a girl is interested or not? Do you think I’m sitting across from my date thinking about if she likes me? “Oh I hope she thinks I’m witty!” The only thing that matters is if I’m interested. In that case I proceed and do what an interested man does: go for sex. Otherwise I pass so guys like you can take her out to help her get over guys like me. Stop acting like a woman.

Kathryn says,

I’m stuck on the “two dates” part of your question. It seems you get a good number of second dates, but not many third dates.

Several women I know (who are nicer than I am) give pretty much anyone two dates. Sometimes women get to a point where they feel they’re rejecting men too soon, or not finding love, or not being as “open” to the universe as they should be, so they decide they’ll go out with just about anyone who asks, and give all those people two chances/dates, no matter what. I also know at least one guy who gives every woman he meets on the internet two dates so that she won’t think he didn’t find her attractive (as she might if he never called again after the first in-person meeting).

Also, if you don’t make any kind of move on the second date - not even a short kiss goodnight - your date is going to think you’re not attracted to her and/or gay and not want to bother with another one. I’d find the guts to give these women at least a kiss if you really want to see them again. Would that really be so bad?

34-year-old Teenager writes,

I’m a 34-year-old female who hasn’t dated in 6 years (it was a disaster of a date) and hasn’t had a boyfriend since she was a teen (the reasons for my near-non-existent social life were self-esteem issues in my twenties, then the demands of developing my career in a field that is typically 99% female–I just shut down the romantic/sexual side of me). I always had great friendships with men, but little romance. But things have changed and as I’ve developed greater confidence, my male friends and co-workers rave about me (unfortunately, they’re already married) and are cheering me on as my social life develops..

Now I’m out of that all-female field and enjoying the male attention I’m getting, including a date with an older man (age 50) in a couple days. But I’m such a neophyte to both the dating scene and the physical aspects that I’m more like a teen than a mature woman in this realm, and I’m terrified of either misunderstanding my date or giving him unclear signals. And I’m further scared of him making a move on me while not having a clue that I’m not just a virgin, but almost totally inexperienced at every level and thus misunderstand my responses. I’ve got a lot of passion and desire, but no clue how to express it in ways that will get me what I want: his awareness that I’m very attracted to him but I need some lessons.

As an example, he’s headed on a business trip and came to say goodbye to me (he’s been dropping in on me at work for weeks–he works in the same building). He gave me a half-hug goodbye as he said he was looking forward to our date. Then after I said something teasing/flirty as he started to leave, he said affectionately, “come on over here” and put his arm out to me again. I just snuggled my head below his shoulder because I was afraid if I looked up at him and made eye contact in that position he would try to kiss me. In short, I panicked, even though I would’ve loved a kiss.

He’s wonderfully sexy and all alpha male (yum!) while also being gentle and rather intuitive. How do I help him understand without scaring him away?

DCB says,

1. Relax. Dating is not a do-or-die activity that requires you to have all your loose-ends tied. If it doesn’t work with this one, you try again until it does with someone else. The worst thing you can do right now is worry about intentions or signals. If you’re not a mind-reader, don’t act like one.

2. Relax. There is nothing anyone can tell you right now that can magically give you the experience and know-how to make your date with him go off without any awkward moments. Just do want you want to do: if you want to be kissed, let him kiss you; if you want to tell him that you haven’t dated a lot, go ahead and tell him without making a big deal out of it; and if you want to have sex with him, tell him to be gentle and enjoy it.

3. Relax. I’m sure with your career you had a path that was mostly clear, through concrete goals and milestones that pushed you higher up on the ladder. Dating and relationships are more fluid, with less cause-effect (doing X will not always lead to Y). Set your expectations low and go with the flow. Deal with sticky issues only when they arrive.

Kathryn says,

I remember feeling like that when I was 15 and had just spent years at all girls school, living in an all-female house, and suddenly found myself in a co-ed environment with boys EVERYWHERE. To me, it seemed all the other girls were totally comfortable with guys, while I viewed them as another species speaking another language. Daunting.

But you just have to calm down and step in, no matter what your age. If you want to kiss, kiss. If you want to say yes to a date, say yes. If you want to strike up a conversation with a guy, do it. The consequences are never as dire as we think, and the rewards are usually worth the risk, particularly when you can chalk up every little success and failure to gaining experience.

In this particular situation, if he’s as intuitive and willing to take the lead as you say, I’d tell him you’re shy and inexperienced if you ever get skittish around him. Let the circumstances of your budding friendship/relationship dictate how much you tell him and when. Then don’t sweat the outcome.

Easier said than done, I know.

blog groupie writes,

This is ridiculous, but I’ve developed a crush on a guy whose blog I’ve been reading for a while. I don’t actually know him. Does this make me crazy or just pathetic?* Is there any non-stalkerish, minimally pathetic way for me to act on this crush? (Blogger boy is DC-based) I’m sure if I actually met him the crush would disappear instantaneously. Short of that, should I just stop reading his blog?

*And does it make it more/less crazy pathetic if I think I’m prone to crushing on a guy I don’t know in part because I don’t actually know any straight, single guys? I have a good social life, but everyone I know is either married, female or gay, and my hobbies tend to attract mostly women and gay men. No one I know even knows any straight, single men! I know they exist, but I don’t know them.

DCB says,

No, it’s not pathetic if you have a crush on me. In fact, it’s quite natural to become attracted to someone whose writing flows like a gentle river on a crisp, autumn day.

All kidding aside, I suggest you send a short, complimentary email that has a slightly flirtatious undertone (a couple smiley winks will do). If he is open to meeting a fan, he should have no trouble taking it to the next stage after a picture exchange. The thing that bothers me is that I know for a fact there are female fans of mine out there that are too timid to make that first contact. The reward ends up going to the girl who doesn’t mind taking a risk.

Kathryn says,

Ah, your very first blog crush. How cute!! But be forewarned: when you’ve never seen the blog writer in person (not even in pictures), but have developed romantic feelings for said writer based on your own idealistic interpretation of the posts you’ve read, it’s a highly dangerous game - people are rarely what we want them to be. So try to keep your expectations low.

However, like DCB says, bloggers love to hear from “groupies.” Everyone blogs at least in part from a desire to connect with others, and have others appreciate their work. There’s a narcissist in every blogger; that is universal. The degree of narcissism is the only variable. So send a short, fun email with specific reference to a certain post. Try and strike up an email conversation. Youll know soon enough whether the blogger is interested in meeting new people and, specifically, in talking to you. It’s a pretty small risk, in my opinion.

And as for your question about stopping reading his blog… Let’s be honest. Could you? I doubt it!

Anonymous writes,

Hey, DCB and Kathryn. Maybe you can help me with this one…

Last summer I met a guy while I was out. I thought he was kinda cool and cute, but we didn’t exchange numbers so I didn’t see him for a while after that. I wasn’t looking for a guy at the time so it was no big deal.

During the winter I ran into the guy and we started making out. It was nice, we exchanged numbers, and I went home slightly interested. Over the next few weeks he seemed extremely interested in me. Wanting to keep things casual, I’d call him from a club or some other place and tell him to come over if he wanted. Over time we developed a great rapport and eventually had sex. There were rough moments– he is bipolar and has some other issues that sometimes manifest themselves– but I was patient and understanding because I had such a great time with him otherwise. We went on the best vacation together just a month or two after we started seeing each other.

During this time he has had some things going on with his ex. He says he is still in love with her but she no longer loves him. It sounds like she treats him horribly and is only using him for money and favors now. He’s aware that he’s being taken advantage of, but is still emotionally attached to her. He tells me I’m perfect and exactly what he needs right now, but he can’t love two people at once. Often he won’t have sex with me because he feels like it’s wrong. He geniunely wants to get over her but just can’t.

Meanwhile, I’ve fallen for him and I’m too attached to leave now. I’ve had no problem being patient and letting him take the time to get over her (I still don’t mind keeping things casual). I figure if I’m patient and understanding he’ll eventually come around, but this has been going on for months and it doesn’t seem like he’s making any progress. Eventually I would like to start dating him seriously, but I wonder if that’s ever going to happen at this rate.

The ex is leaving the country for a couple weeks so he won’t be seeing or hearing from her for a while. I was wondering if I should use this opportunity to make some kind of move, but I don’t know what that would be. Suggestions? Or am I wasting my time with him?

Kathryn says,

I think you’re wasting your time waiting for him to come around and realize he loves, respects, and wants a serious relationship with you. Listen to what he’s saying. He said you’re “exactly what he needs right now” - as in, no strings attached sex when he wants it and isn’t feeling too attached to the ex who doesn’t want him anymore. He told you he “can’t love two people at once” - as in, he’s too busy being in love with someone who doesn’t love him, and doesn’t like/love you enough to let that go. It makes no difference whether his ex is in the country or not - she’s clearly a big part of his demented emotional world no matter what kind of contact they have.

DCB says,

Sounds like you have a nutcase on your hands. So everything is great except for the awkward emotional moments and sexless nights? And you want to wait for things to “come around?” Right, I haven’t heard that before. The only move that would make this better is scheduling him an appointment with a psychiatrist.

Anonymous writes,

I’ve been dating a woman for about a month now, and am struggling with how quickly to let the relationship progress. She is eager to hang out and sleep over regularly. I’m not necessarily opposed to that, and often would like to hang out myself. However, I’m nervous about letting things move too quickly, in part because I see a lot of potential in the relationship, and don’t want to have things flame out after becoming too intense too early.

I realize this is one of those situations which requires a lot more information about the people/relationship involved to provide concrete advise, but I was hoping to get your and your readers sense of how much time they typically allow to pass before a relationship progresses to the point that you are sleeping together 3 or 4 nights/week.

Thanks in advance.

Chaco says,

I have some strong opinions about this one. I believe firmly that the kiss of death in a relationship is “too much, too soon.” When it’s too much too, too soon, the girl can go from “wow this is great!” to “wow…I need a break” very quickly, and the momentum can be lost just like that. You don’t want that kind of negative vibe in your relationship until you have built a solid foundation.

So easy, just cut back on the dates from 3-4 to 1-2 per week, right? Well…no.

The tricky situation you are in is that if you pull back now and only see her 1-2 times per week, she may feel slighted and the relationship can lose steam because she feels you are not that into her. So, I think the way to manage this is to make sure that you are not also talking for a long time every night on the phone and sending multiple emails or texts to each other throughout the day. In addition, make sure it is *she* who is calling and suggesting the ‘extra dates’ (the ones over and above what you would want). If she is suggesting them, she can’t blame you for smothering her.

I also highly suggest you carefully monitor her mood when you are together. Does she still have that excited quality when she is with you? Or is she starting to seem worn and a little distant? If the first, you can keep seeing her as much as you are, provided she is pushing for the contact. If the latter, you need to come up with excuses for why you are “busy” on some of your usual date nights, so that there is less frequent contact. When you feel that the slightly less frequent contact is re-igniting the flame again, you can start permitting more dates.

By the way, having a woman want to sleep with you 3-4 times per week from the beginning is not the worst problem in the world to have. Give yourself a self-esteem boost and chalk it up to your amazing bedroom skills. Hey, you she can’t help it if you’re *that* damn good, can she? If it does flame out with her, your increased confidence will help you land a new hottie quickly.

Kathryn says,

I think it’s much more a matter of intimacy and emotion than it is “three weeks” or “three months” in this situation.

That said, the excitement of a new relationship only lasts a relatively short while, no matter how good and permanent it may turn out to be in the future. So you should do everything you can to savor it. I would make sure that you spend some nights doing other activities - football or poker with your guy friends, or playing softball, or some other legitimately no-girlfriends kinds of events. Any time you turn down a chance to see her in favor of something else, be sure to say, “can I see you tomorrow or the next day, though?” and show you do want to spend time with her. A little anticipation helps, too - “I know I can’t go much longer than that without seeing you.”

Also, in the first sleep-overs, try to make them as non-domestic as possible. As in, no overnight bags, no seeing each other get dressed, etc. Avoid sharing the “bad naked” as long as possible, and keep the magic alive as long as you can.

sue writes,

Ok. I have been dating a guy for two yrs. He likes to check out other women when we are out. I know this, and it makes me feel uncomfortable because it is just like he is on another planet when when go out. Too much too look at!!! He of course denies it. The other thing he does is always walks behind me, not along side me when we’re out, and I told him i think it is because he wants to be freer to look at other women. He thinks I am nuts, but I don’t know if I am over-reacting or not. It just hurts my feelings. Any advice?

DCB says,

The problem here is not his wandering eyes, since it’s a normal pastime for men to check out other women. The problem here is your taste in men. It is very very hard to get caught checking out other women; I’m a huge pig but have never once been caught. If you are dating a man that you catch looking at women, that means he is a huge idiot that deserves to be removed from the dating pool. Why would you want to keep a man like that in business?

Kathryn says,

There is a big difference between “checking out” and completely ogling, disgustingly fawning over, or eyejamming. If your boyfriend is just occasionally looking at other women, I wouldn’t sweat it. He’s male, and he knows not what his eyes may do. It happens.

But if he’s constantly staring at other women, ignoring you, AND never walking with you in public (as in, pretending you guys aren’t together), you have major problems. That almost sounds like he doesn’t want to be in the relationship. Or to publicly acknowledge that he’s with you. And that’s miserable.

Bottom line: anyone who tells you your feelings are insignificant and that you’re nuts probably doesn’t care much about you. For those words to come from a boyfriend of two years… well, that’s shitty. Dump him.

He’s Just Not That Into Me…Or Is He? writes,

I started dating this WONDERFUL guy a couple of months ago. For the first month
or so we were on the same page, but now I’m afraid that either (A) he’s losing interest, or (B) I let myself start to like him too much and am now obsessing for no good reason. Here’s a quick run-down:

*** FIRST 6 WEEKS ***
After our first date, we saw each other pretty intensely. We knew his job was sending him overseas for a month soon, so we saw each other about 11 of the next 14 days. We both even called into work sick one day just to have more time to spend together. He introduced me to all his friends and would say to them how much he liked me in front of them. He would send me emails from work saying he couldn’t seem to get me off his mind. I’d tell him I was suffering from the same ailment, so he’d drive across town to meet me for lunch. We spent the night at each other’s place several times. No sex; just quality time. (In fact, he didn’t even make a move which I took as a sign of respect.) He even gave me foot massages before work! This isn’t usually how I start things off, but it just sort of happened and it felt wonderful.

Overall, I found him to be the most refreshing guy I had met in a long time. I remarked to my friends how nice it was to date a guy who didn’t keep me guessing how he felt about me. The only 2 things that might have been red flags were: (1) He mentioned that his friends call him a ’serial monogomist’ because he was always in a relationship, but that for the first time in his life, he was in “dating” mode. It’s been 2 years since his last relationship; (2) He mentioned having just called things off with another woman he had been seeing. I asked if he had any other people he was seeing. His response was “Yes, but I’m working on bringing that to a resolution too” (which I took to mean closure).

The third wild card is that his job requires him to travel A LOT. Every other month, he has to go overseas for 3-4 weeks. He comes home for 2-4 week intervals in between. His first trip occured around week 3 of our dating, and he was gone for a month. That meant no face-to-face time obviously, but he called every other day so I felt pretty comfortable that things were looking good despite the distance.

*** THE RETURN ***
Once he came back from his first trip though, thing seemed a little different - certainly less intense. To be fair, he only had one week at home before heading overseas again so things were pretty hectic for him. During that week, we went to dinner twice and hung out a his place one night. Seeing someone three times in a week probably sounds normal, right? Thing is, I couldn’t help but feel like he was being a little bit distant. Sure, we hung out but it kinda felt like our plans were always tentative and only came together at the last minute. Whereas before he seemed to wanna squeeze in as much time with me as possible, this time he seemed to want quite a bit of time on his own.

Maybe he was just being normal for a guy who only has one week in country before spending another month overseas, but given its stark contrast with the voracity with which we were spending time together our first two weeks, I felt like something had “happened” to make him less interested.

During that last night that he was in town, I remarked that he seemed a little different and asked him if I had done anything to make him mad or put him off. He seemed confused by my question and said that it had just been a very busy week for him. My response was, “Yea, I know you’ve been busy, but you also seem a bit distant.” He didn’t really respond to that, except to say that he wished he could come up with something funny to say that would lighten the mood. We changed the subject.

TO BE CONTINUED ?????????

He’s now overseas for another month, and unfortunately, he’s in a country from which he can’t make phone calls this time. He has been there about 2 weeks, and while he does respond to my emails, he never really initiates contact (again - stark contrast to all the overseas phone calls initiated by him during his first trip). I’m thinking I should stop emailing him for a while to see if he takes any initiative; somehow I think it’ll give me a more accurate guage of his interest. Of course, I hate feeling like I have to calculate my moves now, as not having to do that is what I found so refreshing about him in the first place.

I’m not sure if he’s really pulling away, or if I’m just overanalyzing what would be a normal dating relationship (albeit complicated by periods of distance). I feel like we started out on Cloud 9 together but that he shifted down to Cloud 5 without really telling me. I’m kind of starting to obsess about it. That’s not really me, and I know it’s not really healthy. But I also know that I wouldn’t have let myself get to this point if I hadn’t initially gotten signals from him that he was as intensely into me as I still am into him.

He’ll be back in 2 weeks, but I’m not really sure I’m going to hear from him when he gets back. Am I overanalyzing or should I be preparing myself to move on? I’ve gone out with a couple of other guys - just to have something else to think about - but I don’t think it’s working because I still think about him all the time. God, I hate when guys leave a woman guessing!!!

Home Improvement Ninja says,

“now I’m afraid that either (A) he’s losing interest, or (B) I let myself start to like him too much and am now obsessing for no good reason”

Well, you seem to think you’re question is an “exclusive disjunction.” As if the answer to your question couldn’t be both that he is becoming not interested AND you are obsessing too much and overly attached. But rather than wax on about Formal Logic, I’ll answer your dating question.

Why I think you’re overly attached and obsessing too much:

a) You’ve only been dating this guy for two months and during one of those months he wasn’t even in the country.

b) you haven’t even had sex yet. (but he gave you a foot massage? not even going there) but you’re worried enough to write to Kathryn about it.

c) you said you saw each other “11 of those 14 days.” Why are you counting? Don’t you think that’s mildly obsessive?

Why I think he is losing interest:

a) his “other relationship” is either giving him drama about breaking up, or he is getting more serious about her, which affects the way he sees you.

b) your desperation may be freaking him out.

Plotting your dates out on an Excel Spreadsheet isn’t helping you, girlie. Why don’t you stop overanalyzing the situation and take things as you would in a less-intense relationship? The Tao Te Ching tells us that

For those who practice not-doing,
everything will fall into place.

I think your desperation/insecurity is very off-putting. I was put off by it, and I’m only reading your letter. I imagine that he is getting putt off by it because he has to deal with your insecurities in person. Insecurity is more repellent than cheap perfume so your obsession about the relationship fading out may turn it into a self-fulfilling prophecy.

I think moderation is the key, The Great Book tells us that:

He who stands on his tip toes, does not stand firm,
He who takes the longest stride, does not walk fastest.

If this downtime isn’t a result of drama from the other girl he’s dating (and that’s a pretty big “IF”) Maybe this is your cue to take it a little slower and less seriously. I think a relationship that progresses slowly is better than one with fireworks that fizzles out quickly. A relationship is like a dance. If he is now doing the tango, you should stop waltzing. Or better yet, why don’t you listen to the music and figure out which one of you is off beat. Wow, that metaphor smells like fromunda cheese.

And speaking of bad metaphors…Getting intense feelings early on is risky. On Wall Street, if someone takes a risky position, they usually protect themselves by hedging that position, and adjusting the hedge as the market moves against them. This “dynamic delta hedging” works as well in assessing relationships as well as delta hedging Latin American equity options. Take it slowly and open up if you feel it’s warranted and hold your cards closer to your vest if you feel the relationship is going the other way. Also, never go short on Chilean bonds. Trust me on that.

And rather than guess about what he meant by “bringing that to a resolution” why don’t you just say “Huh? Resolution? WTF are you talking about?”

Kathryn says,

If he’s leaving you guessing, he’s not interested. Guys who like you stay in touch. They don’t make you freak out all the time. It’s really that easy.

“Am I overanalyzing or should I be preparing myself to move on?” Prepare yourself to move on. Keep dating other guys. And before you know it, you’ll think about him less and less. Especially once you find one who doesn’t leave you guessing.