Q. Dear Alannah,
There's this girl at my new job who I'm interested in, and I don't know how to strike up a conversation with her. We both work in a call center and are both usually on the phone with customers. We've talked briefly when I sat with her for on-the-job training when I first started working there, but we don't work directly with each other, and my main concerns/questions are how to strike up a conversation without it being awkward. Odds are I will not be seeing her randomly around the office where I would be able to engage in small talk. I would probably have to start talking with her at her desk and the issue with that is, being able to do it in a non-awkward and meaningful way. How would this conversation go, how far should the conversation go and what is the next step in the process?
A. Dear Tongue-Tied,
The best way to engage her in conversation is to wait until you can catch her off the phone sometime and then walk by and engage in some small talk. You could ask her a question about something related to a call you had; you could start out by saying something like, "Hey, can I ask you something? Everyone around me is busy, so I was wondering if you could help me out for future reference." (Then, make up a problem you had or ask her a real question, and then after that lead it into some small talk!)
Or, another way is to try to catch her in your workplace break room when you know she may have a break and then break the ice. This will require a little more creativity on your part, but it can come naturally if you don't think about it too much. If/When you see her in the break room, you can just make small talk, like, "Man, I've been getting some crazy calls today!" (and then tell her a story about a call you had today or some other day). You could even say something such as, "Hey, do you know where the gym is? I'm thinking of switching to the one here at work, but haven't had the time to go sign up." Generally, asking her about something related to work is safe, and she'll most likely remember you as being new since you sat and trained with her, so it'll be believable. If you have a feeling she doesn't remember your name, before you leave the break room, remember to reintroduce yourself, and maybe say, "I remember sitting for training with you." No matter what you talk about, remember to do this, so that next time you see her around, she'll remember your name!
If you happen to bump into her somewhere else besides seeing her at her desk or in the break room, like for instance in the cafeteria at work, that's also another chance for small talk. No matter where you see her, use what's in your immediate environment as a way to start up a conversation. If you're in the cafeteria, you could say, "Everything looks good, but I could stand to get something somewhere else. Do you know of any good restaurants around here?" The easiest way to break the ice is by using your surroundings to come up with a topic for small talk.
When you're talking to her, keep the conversation to just a few minutes. Once you've broken the ice, you have now established rapport with her, so the next time you see her, you can say hi and ask how she's doing. Whenever you talk to her, keep the conversation light each time, and don't let it drag out too long. After you've talked to her a few times (say after 3 or 4 times, or when you feel that it's most natural), then ask her if she'd like to grab lunch sometime (such as in the cafeteria, to make things easier). By talking to her a few times first, you can gauge to see whether or not she'd be interested and if she'd say yes. If she seems friendly and approachable when you talk to her the first few times, I say go for it. If she seems nice but distant, wait awhile first.
I hope this helps, and let me know if you have any questions. Good luck! ;)