First Date DC

“but seriously, when should i call?”
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April 18, 2006

Step it up

Confused in DC writes,

I have been sleeping with this guy for a few years. It is a FWB situation that will not end. We both work hectic schedules so the limited time we share has been ok with both of us. We get along great and the sex is Awesome. How do i flip the script and turn it into more or are we doomed the be hook up buddies.

Kathryn says,

You’re doomed to be hook-up buddies. If you want more, and you don’t mind losing the hook-up buddy arrangement to get it, tell him. He could want to buy the cow. You never know.

DCB says,

Okay let me pretend that I’m that guy for a second: “I’m getting laid on the regular for years. I have a totally sweet set-up where I don’t have to take her out, put up with her bullshit, or meet her parents. God I’m so lucky. I hope this doesn’t end until I find a hotter chick.”

You should have worked the relationship angle a little bit earlier, the third date, not the third year.

April 17, 2006

Virgin blues

Feeling Negative About Ownership writes,

I’m a 27 yr old virgin, and I work for this huge firm as general counsel. I’ve dated, but never felt compelled to take it beyond kisses. Serious “relationships” do not interest me since I am not ready to settle down. So here’s my problem: I am only attracted to older men–not by a decade, but several decades.

About 6 months ago, I was assigned to work with this non-profit as a part of our firm’s pro bono requirements, and I met this 51 year old man. He’s is the executive director of the organisation and exhibits every sign I’ve ever wanted in a man and then some. He’s married, of course, with two small children (he married very late in life). Ex. He truly cares about the people in his organisation; he always tries to do the “right” thing; and he’s got these laughing eyes and smiles often…. yada yada…

All I think about these days are hot and dirty sex with the man and I have NEVER had sex. It can’t be curiosity because I can have sex with this guy that I am casually seeing (he exhibits all the signs of willingness). On top of everything, I think my 51 year old has also got the hots for me as well (although, he’ll never do anything about it because he loves his wife and children). I’ve been in agony for over 6 months. Point me the way in or out.

Thanks.

DCB says,

I hope you are not expecting me to give you advice on how to have sex with this man. Judging from your virginity status - and your ability to lose it right now if you wanted - I can tell you are not serious about having sex. You are stuck in some make-believe land where people at 27 are not having sex. Please leave this guy alone and don’t destroy his life and career just because you are having another one of your fantasies. You are way past the age to save your virginity for “the one.”

You are using your virginity as a power device, just like anorexics do with their weight, to show that you are in “control.” Don’t bring an honest man down with you.

Kathryn says,

This is one of those rare times I agree with DCB. Please go on a couple of dates with a single guy your own age (or at least an unattached older one) and let him have your cherry. Once you’ve passed this huge milestone, I think your crazy sexual feelings about unavailable men should subside. If not, please, PLEASE seek professional counseling for your daddy issues.

April 14, 2006

These foolish games

Anonymous writes,

I can’t believe I’m resorting to this, but what the hell. I just need someone to make sense of this for me because I can’t do it on my own.

This guy I’ve known for a year asks me out. Finally. There had been a few clues along the way that he was interested, but I usually tend to brush those off. But at long last he asks, tells me he’s wanted to ask me out for almost a year. I give him my number, he calls, and a week later we’re having dinner. And it’s wonderful. From the very first moment it’s romantic with lots of eye contact, little touches here and there, pulling me back to kiss me when I get up to go to the restroom (a little more kissing later, but that’s it). Telling me how beautiful I am, how he can’t believe we’re finally on a date, how happy he is, and talk of future dates (but no actual plan).

And then? Yep, you guessed it. Nothing! That was almost two weeks ago and not a single peep. And you know, I get the whole he’s just not that into you thing, but it simply doesn’t make sense in this case. So I have to ask, is there something I’m missing here? If it makes any difference, I’m mid-30s and he’s mid-40s, so I think we’re well beyond the childish games.

Kathryn says,

Did you check the obituaries? Maybe he died. It happened to Miranda.

But seriously, I’m so sorry to hear this happened, and even sorrier to say I can’t explain it. Some men live for the fantasy, and fully commit to it in the moment, regardless of the consequences or their true feelings. And when they aren’t actively living out their little fantasies, they have no use for any part of it, and it might as well not exist for them. Your guy could have been making it the perfect date, so that he got to go home and think, “yeah, that was the perfect date,” but have no interest in making it anything more.

I think you should maybe just pretend he died.

DCB says,

Are you sure you didn’t have sex? I’ve learned that many girls have weird exceptions when it comes to sex, like when a girl once told me that if the guy doesn’t cum, it doesn’t count. Right.

I’m going to say that his only interest in you was seeing if you liked him or not. He is not a closer, and just gets his kicks by testing the attraction waters. Maybe he plays a little game with himself, “winning” by making out with a girl he has been eyeing. I don’t know. If I was in that guys place, I would have at least had sex with you before dumping you. At least then you would know that I was in it just for the sex. But take you out to dinner for a kiss? Gay.

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April 13, 2006

Online dating rights

Singleinthecitydc writes,

Stupid online dating. Sorry if you’ve covered this before, but…

Say you meet someone online. Email each other, agree to meet. After the first date, you see no glaring signs of pshcyo-ness/mutant body parts and you continue dating, with dates becoming more frequent as time passes. It’s been several months. You’ve slept together. You’ve met each other’s friends. (But you haven’t had the dreaded DTR talk.)

At what point should the parties involved be expected to pull their online profile/stop logging in every day?

DCB says,

While it would be reasonable for him to take it down about a month in, just get one of your cute friends to send him an online ‘wink.’ His response should tell you where you stand. Though I have a feeling that you are not the only girl he is banging right now.

Kathryn says,

I’ve seen mentions of this situation here and there on random blogs. People who’ve met online and had a few dates with someone see the other person is still logging in to the dating site, and what does it all mean, and can I ask him/her to stop!?!? infinity. Here’s the thing: maybe the other person is logging in to see if you’re logging in. Maybe they are getting messages or winks or what have you, and logging on to look at them out of curiousity, but not responding to any of them, because you make them happy. Maybe they have friends who are majorly active on the site and want a second opinion on some poor shmo’s profile. Maybe they think they can do better than you and are going to keep looking until they find it. It could be ANY reason. The only way to find out is to talk about it.

I don’t understand why the DTR is so dreaded. If you’re sleeping with the person, seeing them a lot, meeting the friends, etc. shouldn’t it be about time to discuss exclusivity in general? You don’t have to bring up the dating sites as part of that conversation, though I do know couples who met online and got a big kick out of changing their profiles together to “inactive” or “in a relationship” or whatever means “taken and definitely NOT looking” on the specific site. But until you talk about the status of your relationship, regardless of how long it’s lasted and what’s going on, all bets are off. You can’t assume anything.

April 12, 2006

Forest for the trees

Why Ruin a Good Thing writes,

I’ve been dating my girlfriend for well over a year and we have a great, healthy relationship. The problem is I can’t stop thinking about this other girl I was good friends with in college that I’ve always had a crush on. She had a boyfriend back then but is now single, yet we lost touch somewhere between that time and she does not live in the area anymore. I keep trying to forget about her but keep asking myself what could’ve been. I thought while dating my current girlfriend that the thoughts would go away, but unfortunately they’re still persistent. It’s seriously driving me crazy. Why can’t I just let it go?

Kathryn says,

Maybe because you’re kind of an asshole who isn’t happy with a “great, healthy relationship” that has lasted over a year? You can’t be serious about your current girlfriend if someone you had a (probably) unrequited crushed on years ago, who doesn’t even live locally, occupies your every waking thought. I think you should end things with your girlfriend, then contact this woman of your dreams. When it fails miserably, and you are left with NEITHER girl, you will have learned a great lesson, and may appreciate your future relationships.

DCB says,

I guess your relationship isn’t that “great” or “healthy” if you are thinking sexy thoughts. What Kathryn said, and…

You can’t let it go because it’s human nature to always want what we can’t have. There are two roads you can take here: (1) Forget about the other girl forever, or (2) Silently pursue the other girl, get her in bed, and validate your meaningless existence. Guess which one I recommend? Your girlfriend is probably cheating on you anyway, so technically you aren’t doing anything wrong. Good luck.

April 11, 2006

Not-so-easy lover

Maggie writes,

I’ve been on three dates with a guy that’s very successful, 31 yrs old, cute, drinks in moderation-1 or 2 beers, overall good guy. We met through my aunt’s friend. The problem is that our dates consist of happy hour right now, never dinner or something romantic. We haven’t even kissed yet!

The last time, third date,we went out we had two drinks and he says “Want to come back to my place?”, very random since we were at a bar, and I said, “ummm okay” I made it clear that I would have to leave soon after as it was getting very late and I had an early meeting. I’m not a prude believe me, but I do think a guy has to do some work before I’m going to want to sleep with him especially if I’m sober! So we kissed goodbye at his place, great kiss, but I don’t think I’ll hear from him again b/c I didn’t put out. Am I wrong to think that? Should I wait for him to contact or send an email to say hi??

Kathryn says,

Until he kissed you, I thought he might be gay. He still could be, but I’m going to table that as a reason for his behavior.

So you guys have met for happy hour three times. I don’t know if I’d call that three “dates,” necessarily. Has he been paying? Or offering? Is he always the one asking you out? All important details. Based on what you’ve shared, I’m thinking either he’s unsure he wants to invest in dating you or he’s recently been dumped or otherwise heartbroken and is now scared of getting hurt again. Either way, let him make the next move and come to you. If the kiss was really that great, I’m sure you’ll be hearing from him in no time. Whether it’s for another happy hour or something definitively more date-like, I have no idea. Good luck!

DCB says,

So you like everything about him - “overall good guy” - yet didn’t give him more than a kiss by the third date? At least rub it a little.

He got frustrated that he was receiving no action after taking you out two times. He thought a third date was perfectly acceptable to go for the notch. I sure think so. While he doesn’t sound like a great catch, he realizes that for every girl like you who has sexual hang-ups, there will be another who actually enjoys sex and doesn’t play games. He got tired of your lame-o prudeness and asked out that girl who has been giving him the crotch stare in the office.

Oh, and wouldn’t sending him an email go against your rule of wanting him to do “some work”…

April 10, 2006

Schizochick

Mixed signals writes,

Hey, just wanna say I really love the site. Ok, here’s the deal. I’ve been dating this girl for a little over 2 months. I dig her a lot. All indications are that she digs me a lot, too. But lately, I’ve gotten some mixed signals. For starters, she told me recently that she went out on a date with a high-profile professional athlete “right before or right after we met, I can’t remember” (her job puts her in contact with people like this). I casually asked what happened and she responded that “he was an idiot” with “nothing interesting to say” and “was just trying to get in my pants.” Okay, no big deal, I have to take her at her word as I really have nothing else to go on. Although learning that you might be competing with a guy who drives a car that costs half as much as my condo does (she mentioned the car he drives when telling me about it) and who can probably crush my car with his cock is a tough pill to swallow, no matter who you are (unless you are another rich, professional athlete).

Then this past weekend, we were out and she was pretty drunk and because my birthday is coming up in a few months, she asked if I wanted to go with her to visit her hometown and catch a baseball game for the weekend. It sounded like fun and I said I would like to go. Then we get home and we’re in the middle of getting it on, when she stops and has what I can only describe as a “moment” because I really don’t know what else to call it. On the verge of tears, she tells me how she is feeling overwhelmed with these feelings she has for me and she doesn’t know what to do about them. It sounded like she was really telling me that she was scared of getting hurt or something. I calm her down by telling her I’m not dating anyone else (the truth) and everything is back to normal. Move forward a few days and we’re talking on the phone and she mentions that she had dinner the night before at one of the nicest, most expensive restaurants in DC with a “friend” but declines to elaborate who the friend is (I didn’t pry). This is not the kind of place two girlfriends would go for a bite to eat and talk. It’s a fancy, super nice, super pricey, special occasion/date place. You only go there if you are celebrating something very special, you are trying to impress someone, or you can drop $300 on a dinner for two without thinking twice about it.

So am I getting mixed signals and if so, how are you guys reading them? Thanks.

Kathryn says,

Yes, she’s definitely giving you mixed signals. Part of the reason may be insecurity, as evidenced by continually playing the Professional Athlete card (assuming he’s the guy from the fancy dinner). But part may be your fault, too. Think back objectively about your interactions. When she was drunk and tearily confessed her confusing feelings for you, and you told her you weren’t dating anyone else, did she give you the same assurance? Did she ever say she’s not dating others, even though she’s having all these feelings for you? Has she ever called you her boyfriend? Has she gone through with concrete plans for your trip to her hometown, or is that all just talk? Sometimes when I am questioning the extent of a guy’s interest, I think back on previous communications and try taking his words at face value only. Quite often, that gives me a much different message than I originally found there, when I was searching for anything positive to hold on to. Do yourself a similar service. Step back, re-evaluate, and move on if you find she’s not putting in as much as you once thought.

DCB says,

I don’t think she is sending you mixed signals at all. She is losing interest, dating other guys, and you come back with “I’m only dating you.” She is just hanging on to you until one of those professional athletes doesn’t dump her after sex. If even the rich guys aren’t putting up with her bullshit, why are you?

April 7, 2006

Duh question of the year

so what do you think? says,

Here is the explanation- i met him on match.com a few weeks ago- we went out for drinks once and it was fun- i wasn’t blown away though. he called and asked me out for dinner- i said, yes, later called to cancel b/c i had to take an exam on Saturday (i’m a law student) and I needed to study that thursday. anyway, I’d appreciate you’re response- I’m not pressed for this guy, but I”m still curious!

The email:

Hey, so..how did you do on your test?? Hopefully you were able to celebrate with your friends sat. evening. My Saturday consisted of a lot of waiting in line, followed by?a lot of drinking :\ ugh..a little hungover today. I went to this outdoor St. Pat?s day fest in ballston. Waited in line for 2 hours. I had friends that were coming later who definitely weren?t going to get in, so I didn?t stay long and met with them back by where I live. Beautiful weather this weekend!!

Oh yea..my new car. It was actually a spur of the moment purchase. Work has been slow lately, so Wednesday morning, I decided to check out carmax online. I searched both in this area and the Richmond area where my folks live. I found the eclipse at the Richmond store, but they could not hold it for me til the weekend, and other people had been looking at it..so..I asked my boss if I could take off the afternoon, which he let me, and I drove down to Richmond, bought it, and drove back in the new car that night :) Ha..a rather expensive impulse buy.

Let?s grab dinner this week. Does Thursday still work best? We can still try that Houston?s place. I?ll give you a call tomorrow and we?ll figure out time and directions and all that. Do you still have company in town? Didn?t want to bug ya today if your friends were still in town. Well?Now that I?m finally vertical, I guess I?ll try to get out and accomplish something today :) Talk
to you soon…

DCB says,

Phew I actually made it through his really boring email. So let me get this straight: you flaked out on a guy, he asked you out again to dinner, and you are wondering what HE thinks? Isn’t it obvious that he wants to bang you? For a law student you are pretty slow.

To the men: I don’t recommend asking a girl out through email. When you ask a girl out on the telephone, you instantly know where you stand based on how she responds. Does she pause for a long time? Does she come up with a lame excuse? How quick does she make a counter-offer? In email she has all the time in the world to carefully construct an answer that doesn’t give you any hint of how you are progressing in the seduction.

Kathryn says,

Yeah. DUH. What guy writes emails that long when he doesn’t like you? He’s also trying to impress you with his busy social schedule, disposable income, and attention to your plans. HE LIKES YOU.

April 6, 2006

Doomed

TryingtoRecover says,

I have been trying to swing this long distance relationship for a little under a year now. I understand the probability of something like that working out is slim, but I was very hopeful through the entire process. This has been very hard for me to let go of because its the first “non sick” relationship I have ever been in. The truth is I didn’t have any desire moving to her area unless I had something else to fall back on other than her. I was afraid that if things didn’t work out, I would atleast have A, B, or C to fall back on rather than just her.

I figured in order for things to work out would require sacrifice and the ideal situation in my head involved us both moving somewhere new. I didn’t know exactly how things were going to play themselves out but I was under the illusion they would if I just hung in there.

Things kind of came to a head about a week ago. She was telling me about how obsessed she was with me. She was telling me how as a result of us interacting, she was unable to focus on what’s going on in her life (i.e. job, internship, finishing school). She told me that she was so preoccupied on what I was doing,feeling, how my day was, that she neglected herself. She told me that she was hanging on to this fairy taile that things would work themselves out in the present time but finally concluded that things weren’t but possibly later down the line. I was able to accept that (it was about the only thing I could accept).

She felt that it wasn’t fair to keep me strung along until she made peace with the situation. I wanted to try something different with her. I wanted to still have her in my life as my friend. I have never done that before. It was so easy to write someone off, grieve, and move onto the next, but I didn’t want that with her. However, she wanted to take some time to work on her and possibly get back to me on a non time limit basis. I was afraid. I was afraid that I would make peace with it in my own mind and then I would get a call which would bring back all these emotions and feelings. I ended up rejecting that idea. The more I spoke with her, the more it hurt. I told her that her words felt like she was sticking a knife in my stomach and she replied that I wasn’t being fair.

Looking back, I know I wasn’t, but I couldn’t see that at the time. Out of anger I told her that I was going to lose her number and maybe the best thing was for us not to talk anymore. This week has been very hard for me but I have mustered up enough energy to not contact her. I don’t exactly want to flip her world upside down. I did send her a card wishing her well and wishing that things ended on a more positive note. She is a very sensitive girl so I made it a point also to let her know that I didn’t hate her and I understood what she took required courage and although I didn’t understand it at the time, I respected it.

I guess what I am looking for by posting this is the possibility of us being able to talk later down the road. I realize that when you love someone that you have to put their best interest at heart. I feel that is what I am doing now. I am just afraid that I will never be able to talk to her again. I don’t know if I sabatoged things to the point that they are unrepairable. I don’t know what the hell I am doing right now. I am trying to hard to heal myself and I would appreciate any insight. Is it better to let sleeping dogs lie or is there anything that I can say or do to change things once the hearts have healed. Thanks

DCB says,

Hey I think your girlfriend already wrote in. First off, you seem like a stand-up guy with a clear head on your shoulders. While you are full of emotion, you also allow yourself to see things logically. It sounds like you just need someone to tell you that you will not lose her forever, that you didn’t mess things up with this girl.

If you were my friend, I’d drag you out, get you drunk, and send mediocre-looking skanks your way, just to get your mind off her for a day or so to allow you to realize that there will be other women in your life. The worst thing you can do is stay at home and go through mementos of your relationship. Let it go for now and if things work out I’m sure you two will find a way to get back together. Right now the best thing you can do is just get out there and talk to other women.

Kathryn says,

I’m happy to be the person to say you may not have lost her forever. I believe that. The card you sent her was an excellent bridge to a future friendship. Yes, you both need time apart, but that note allowed you to say “no hard feelings” in a gentle, unintrusive way. Perfect choice of medium.

I think you guys are young - she hasn’t finished college? - and you’re going to grow and change a lot over the next few years, in more ways than just healing your hearts. When my college boyfriend and I broke up (after five years together, several of them long distance), we tried to be friends right away. It turned out not to be so easy, and he went away for a while. I missed his friendship a lot, but respected his request for no contact. After some time passed, we started emailing here and there and got together for coffee or parties every so often. And now, six years after we broke up, I still consider him a friend, and someone who will always be on my “important news” contact list. He’s the only major ex with whom I have such a friendly relationship, and I know it’s because of the time we took apart.

So enjoy being on your own as much as you can, heal, and reach out to her when you’re ready. I think she’ll be there.

April 5, 2006

One day stand

Lisa writes,

I broke up with my boyfriend in December, and ended up going to Boston for New Years, where I met this really awesome guy. I met him at the bar, through mutual friends, and then I went home with him and we had an AWESOME one DAY stand (complete with afternoon movies). Now, this was my first one night stand ever. I did it because I wanted to get over my ex and because I thought this guy and I had a spark. Afterwards, he didn’t ask for my number, and I didn’t give him mine. I understand that no one wants to date a girl who puts out on the first night, and we live in different states. But secretly I was saddened by this. Since then I can’t stop thinking about him.

I’m moving to Boston in two months and am wondering whether I should somehow get our friends to reintroduce us or ask for his number. Or is this a bad idea? Did he just find me attractive and was too nice to kick me out the next day? Or did we really have some spark and I should try to repeat what we did?

DCB says,

Okay let me give you some one night stand etiquette, since you missed the memo.

1. Men value a one night stand as much as they value Jake Gyllenhaal’s eyebrows.
2. You are easy like every other girl.
3. I like easy girls.

GET OVER IT. I’m sure you’re an awesome person, but this one man has no respect for you. If he wanted to contact you, he would have done so by now. Contacting him would be stalker behavior.

Kathryn says,

Normally, I would say don’t contact him. And I stand by that in this situation - don’t contact him. However, as you have the special circumstance of having mutual friends, I say, let fate intervene. Don’t ask for a reintroduction or plan an “accidental” run-in. Just stay cool, and see if your paths cross again, and if so, how it feels. If you find him attractive, and he’s responding well to you, you can maybe have another one night or one-day stand. But be careful - it sounds like you might want more from him. If that’s the case, don’t give it up so easy next time, okay, Tiger? :)

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