How to Strike Up a Conversation with a Crush

Hi Becca,
I was browsing the internet for help the other day when I saw some of the articles you have written about dating and I was hoping for some help.  You see, I am a guy who has never had a girlfriend before or even been on a date and I am 21.  I have the personality where I don’t go out much and I would rather hang out with just one or two close friends all of the time than go out and meet new people so I don’t have much experience in talking to people I do not know very well.  Recently, I have really started to notice a certain girl in one of my classes in graduate school and I want to ask her out but I feel like I should really like to get to know her better first since we have never talked before.  We have seen each other around campus enough to recognize each other but that’s about it.  The thing is, because of my personality and not going out to meet new people very often, I am not really sure how I can strike up a good conversation with her or how I might be able to keep the conversation going.  Like I said, I have never had a girlfriend before or even been on a date but I really want to get to know this girl better.  Any advice?
A lonely guy



Dear Lonely Guy,

Thanks for the great and very honest question.  First of all, I just want to put it out there that many people in their early 20’s do not have much dating or relationship experience, so you are not alone, and a huge kudos to you for reaching out on here.  Also, I feel the need to say that it can be very difficult and intimidating to strike up a conversation with someone of the opposite sex when you’ve never really talked to them before.  That being said, you are one step ahead of the “average bro” hitting on a girl at a bar, at the gym, a coffee shop, and so forth because you already have common ground with her: graduate school.  You have the opportunity to chat with her in a non over-bearing way and in a non-creepy way.  How many classes do you guys share?  Maybe try sitting next to her in class, or chat her up during your break in class.  Ask her if she thought last night’s reading was boring or if she’s done the assignment for next week yet.  Talking to her about class is a really easy conversation to have, and it should not be awkward for either of you.  Once you start chatting more, start asking her how her weekend was, or what’s she’s up to next weekend.  If she’s open to talking to you about her life outside of class, then you can suggest hanging out outside of class, even if it’s for a study group or an extra credit outing.  (I have plenty of ideas about this because I am actually in graduate school now too!)

If you guys start to develop a friendship in class, then I would ask her if she would want to grab coffee after class at some point.  Another idea is to ask if her she wants to study with you for the upcoming midterm or final.  The only issue there is that you do not want to become her platonic study buddy.  I would start off using the class and homework as a common ground in the beginning, but it is important to ask her about her life outside of class as well.  Ask her about her family, where she’s from, what she studied in college, what kind of movies and music she likes, does she have any pets, and so on and so on and so on.  Showing interest in her personal life will help break the ice and not pigeon-hole you to the study friend from class.

If all of this scares the crap out of you, then I would definitely ease your way in to talking to girls in general.  If you don’t have many friends who are female, I would start talking to more girls in your class, as they are non-threatening conversations since you have common ground.  If you want be ballsy, strike up a conversation next time you’re at a coffee shop with a female barista.  Ask her how her day is going.  The key is to become more comfortable chatting with a girl, which is easier said than done.  If you’re scared and uncomfortable, then she will be able to pick up on that and may feel anxious too.  Being at ease in conversation is important, and eventually that ease will turn into confidence, which is the sexiest thing you can bring with you on a future date.

I hope this was helpful!  Like I said, it really is easier said than done, but it is so important to be comfortable while chatting her up.  If the idea of sitting next to her makes your psalms sweat, then take it one step at a time.  I would definitely trying practicing having conversations with all types of ladies before asking someone out.  But, if you’re feeling good about it and ready to strike up a convo, then I would start sitting by her in class and striking up conversations.  You can do it!!!

Thanks for submitting!  Please feel free to respond if you need further advice down the line!


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