Need input on a "hookup"

We’ve recently hired a new person for our support team. She is a real motivator, I guess you could say. Anywho, all the sudden she wants to know what I think about this security guard girl that works in our building. How I think she looks and all that… I told her that she is pretty attractive. A couple of hours go by, and my new coworker comes back with her phone number :eek:. This was this afternoon. They apparently had a chat about me. My coworker stated that the girl said I was cute. That’s good right? Of course! I’ve never had any hangups about my looks, I’m ok with myself on that front. She also mentioned that she was a bit shy. This must have come up because I told my coworker that I am indeed shy.

However, I’m very poor with my dating skills. As in zero dates. I’m 24. I would really like for this to happen, but, what to talk about? My coworker was like, “you’re gonna call her tonight right?”. And I’m thinking so soon? Huge procrastinator here. I’m not gonna lie, I have fears about this. Mainly the communcation. How to go about it. And most importantly, how to avoid that “awkward silence”. I don’t know much about her . So what are some things to ask, and to keep a conversation going? :confused:

The road to hell is paved with good intentions, ain’t it? I don’t envy you this situation one bit, not at all. But if you’re genuinely interested in this girl, I’d say call her up, introduce yourself, and ask her if she’d like to grab coffee sometime. Get that out of the way, and you can figure out what to do from there.

Call her, and make a date - coffee sounds like a good idea. You don’t have to have a long conversation on the phone. When you go on the date, talk about the things you have in common. You both work at the same place: ask her if she likes her job, the company, how she got the job, what she did before that, what she plans to do in the future… you get the picture, I hope.

Do call her tonight. She has passed her phone number for you to have and is now waiting for a response. The longer you postpone calling her, the harder it’s going to be for both of you.
Meeting for coffee or something casual like that is always a good ice-breaker. You don’t need or even want a set plan of subjects for conversation. Just let it happen.

Before you leave to meet her, brush your teeth, comb your hair and put on a clean t-shirt.


Good Luck!

Yeah, call her. Remember that if she’s using a go-between to get your number, that means she’s just as shy as you are. She’s probably going through all the same doubts and nervousness that you are.

The whole point of the thing is to relax and enjoy each other’s company, not to judge each other or start deducting points for every lull in the conversation, every day you’re “late” in making a call, every day you’re “too soon” in making a call and appearing “too clingy,” etc. etc. Too many people get so hung up on all these rules and first impressions and so on; it’s all stupid. Just relax and have a good time. It’s a date, not an indictment – it’s not your responsibility to impress her.

And don’t sweat the dreaded lull in the conversation, either. It happens, and everybody knows it happens. Don’t be so desperate to fill the silences that you end up saying something pointless. The only “rule” to remember is that if you’re interested, you’re interesting. So ask her what’s going on and let her loosen up and talk about herself, and genuinely listen to what she’s saying. Ask what her job’s like, what she did last weekend, how long she’s lived in the area, what’s her favorite movie or book or type of music – the key is to ask stuff that you’re genuinely interested in, so you don’t have to fake interest while you listen to the answer. And be forthcoming when she asks you the same questions.

Have fun with it.

What Sol said.

Try and find out things about her. Just be aware that YOU probably don’t know what you are looking for, so on this first date, give a lot of leeway to both of you. Don’t expect anything- friendship, sex, etc - from it. Just try and have a good conversation. If things are going well, I would have a plan B: “I was thinking of going to see the new movie now. Want to join me?” And I would have a backdoor “I need to leave in 15 minutes to meet a friend” in case she is nuts.

Be clean, honest, neat and courteous. Save your true self for the third date! :smiley:


I’ve always been the shy guy and until I met my wife, was not good at talking to women I didn’t know, but if you don’t talk to them you don’t get to know them and therefore can’t talk to them. It was a cycle I wish I had broken earlier.

The more you do this kind of thing the easier it gets, and she expressed an interest in you, so you are going to call someone who wants to talk to you. Don’t make a big deal out of it just call her.

I guess we’ll find out today if you called or not. Now that I’ve matured a bit and gotten past some of the fears you have, I can tell you that it’s all bunk. I, like you, made the whole dating process big, important, nebulous and a thing to be feared.

It isn’t.

Would you ever be nervous about going with a guy friend to get a Starbucks megalatteccino? Of course not, but with a woman, suddenly you’re thinking that this could be the start of a lifetime together, and you can’t screw it up!!! Bull. Just go get a cuppa joe and chew the fat. She is not any more special, wonderful or worthy a person than you, so why get worked up?

General discussion topics:
Current events like the Olympics (please, no War or Politics)

And, as a final word of advice… have fun.

Ok, I ended up calling her last night. It turned into a longer call then I thought it would be. Close to an hour. Most of the conversation was good, talking about work n’ stuff. And some parts felt like a job interview. She asked me why I didn’t have a girlfriend. I wasn’t prepared for that one, although I should have been, so stammering commenced. What do I know? :smack: x 10, aleast that’s how it felt. I didn’t let it show though. Otherwise, she wants to do something after work today. We couldn’t really decide on anything as her schedule is pretty insane. But she said she’d call me…

My past is killing me without having never had a relationship. This seems to be my only hangup. I don’t know how to answer those types of questions without seeming to look like a complete social disaster.


I’m kinda shy and sometimes find it hard to talk with women, but for some reason it is much easier talking with you.

Heh, that sounds good!

Ooh, that’s a good one.

And if she looks worried or nervous because her paranoid little brain has filled in the blank with “because you’re hardly like a girl to me” You can say something like “…and I thought I’d be really nervous ’cause you’re so pretty.”
Sorry to be looking for trouble, it’s just when men said something to me like that it was invariably followed by the “you’re just like my sister” or “Let’s just be friends” lecture.
Don’t dwell on your lack of past relationships. When I was single I would have really liked to have had a date with a guy who didn’t spend the evening complaining about his psycho-hose-beast-ex-girlfriend.

I know I shouldn’t dwell on my past relationships, the problem is, is that I don’t have any. Although she still asked the question. So now I’m not sure what she thinks. And yes, I know I shouldn’t care what she thinks. I would think a newbie would be desired. Because hey, I’m trainable!! I’m not set in any of my ways with women, because I have no ways. Wouldn’t this be a plus? They might not get the experienced guy they’re looking for, but they can show me the way much easier because I’m new to it all, right? I’m tellin’ y’all, I’m clueless.

Having never met her, I can’t guess at what she was getting at when she asked why you didn’t have a girlfriend. Maybe she was asking if you are gay or live with your mother. Who knows? People get nervous and say silly things. The point is you said (I hope) that you don’t have one, and hopefully she’ll let it go. If she asks again, you can always say that you’ve been building your career, or you spend a lot of time with some normal-sounding hobby (maybe some sport?).
And yes, trainable is a good thing, if she knows what she wants.

She asked because she wants to know if you’ve just got out of a relationship, and are going to spend all evening talking about your ex. Also, she’s paying you a compliment. She thinks you’re hot, and is amazed that you haven’t been snapped up yet.


Just be sure that now that you’ve made the first call and you guys talked for an hour, that means the pressure’s on. Be sure that you focus on every time you stammered or dropped a question, and be sure that you didn’t say anything that could conceivably be mis-interpreted as lack of interest or too much interest. Any time that an attempt to get together falls through, make sure that you find out whether it really was because of a schedule conflict or whether she’s immensely turned off by you and is trying to get rid of you.

Be ever-conscious of the fact that you haven’t had a long-term relationship before, and devote all your energy to finding out exactly why this is and constantly asking her for help in how to improve yourself. There are a million ways that you could screw this up now, so be conscious of every single one and be ever-vigilant in avoiding them. Over-thinking it is the key!


Or, just take the fact that y’all talked for an hour (!) as a great sign, you guys “click,” and you’re both into seeing each other again. You feel like you don’t know what you’re doing? Here’s a clue: nobody does, and anyone who says that he does is lying. There are similarities in dating experiences, but every couple of people is really different. If you’re really a good person, it shows, and there’s not one thing you can say or do that’ll fuck everything up irreparably.

Or in short: cool! Now keep having fun with it.

OK, so what happened next? You must keep us informed. I was a “late bloomer” too, so I am really interested. Having The Devil’s Grandmother and other womens’ perspective is a rare advantage you should make use of.

Ok… I didn’t forget about the thread. Just been busy with some stuff. I ended up meeting her at her place of work after I got off work Monday. She’s a very hard working girl, and I found out she works 3 jobs :eek:. This is the best we could do on short notice. She wasn’t busy though, so we had plenty of time to talk. I ended up asking her out, and she said the best time would be next week, she needs to free up her schedule. Understandable. I’ve called her a couple times during the week, and so far so good.

I told my friend that I was with her Monday night… Now he knows my situation (being shy and all, no past relationships), and he has the nerve to ask, “did you at least make out with her?”. At least? I couldn’t tell if he was being sincere, or being an ass. Is this what normal people usually do? If so, I’m going to be in serious trouble soon. I have no idea how to initiate the next level, so-to-speak.