Unique first date, and I need advice!

fashion-man-person-wristwatch

robbyj1 asks:

This Saturday I’m going bowling with this girl I met. I met her at a family party last week and decided to take a leap and ask her if she wanted to go bowling. She said yes!

We didn’t get to talk during the family party except for this one question I asked because it took me the whole time to muster the confidence to do it, but for 2 hours, we sat next to each other at a big table with my parents, her parents, and their friends (they are all in their 40’s-60’s, I’m 24, the girl is 21). The point of the party was actually a setup to discuss us possibly marrying each other. Of course, she has to like me and I have to like her first before anything can get done. I don’t know her at all, but from what I heard from them, she is smart (double majored in bio and chem), hard-working, and wonderful. From what I saw, she is model-esque beautiful.

Us going together is kind of date, except she’s bringing her younger brother (18, he was not at the party so I haven’t met him) since in my culture a guy and a girl are not supposed to meet alone unless married.

I have three younger sisters, but they won’t be of any help since they are all vacationing on the other side of the world right now. So it will just be me, the girl, and her brother

My questions to you are:

  • How do I handle this situation?
  • How can I break the ice?
  • What should I talk to her about (remember her bro is there)? How should I talk to her about it?
  • What are some dont’s that I as a guy might think are good, but really its bad?
  • What should I wear? Are khakis, a shirt, and hat ok?
  • Any other advice you can give to my poor soul who wants this to work out well?

Demetrius says:

Well this is a new one, but not necessarily foreign to me. I’ve actually been on a few third wheel dates in my life, but never one where the third wheel was her brother or required to be their because of cultural reasons. Still, I can think of some ways to handle this.

First, I want to say great choice on your part to choose bowling as a date activity. Because there is a built-in fun factor for this sort of date, even if her brother is miserable or awkward, it’s not like you’re stuck sitting across from him at a dinner table. The situation allows for occasional breaks in conversation between you, him, and her so that fairly frequently, you get at least a tiny respite from your third wheel. How you handle the overall situation is simple really, you use this opportunity to talk to her. If you’re clever, you’d even encourage her brother to invite a friend along so he has someone to talk to. If that’s out of the question, it’s not a big hurdle to overcome. Your overall goal is getting to know her, but your secondary goal should be to win her brother over a bit. He’s there as a surrogate for her whole family, so it’s like being on a date with her and her family, which sounds daunting but it can actually work in your favor. I’m not saying that you need to focus on him entirely, but try to include him in conversations when appropriate. You already know she double-majored in college, but you should still ask her about it, then ask her brother if he’s planning to do the same. If you bring up something that’s more general, look food preferences, try to include him where appropriate. Focus on making her feel like a priority but don’t make him feel like a burden in the process.

Breaking the ice is simple really: Ask topical questions. Have you ever been bowling? Are you any good at it? Have you ever been here before? Things like that. Once you run out of those sort of questions you just need to talk to her the way you’d talk to anyone new you’ve just met. Let’s take the whole she’s model-esque beautiful, smart, and hardworking thing out of the picture. What do you know about her? You know what she’s like on paper, you know what her family is like, so now you can focus on what her dreams and aspirations are, her passions, things like that. Sure, she’s studying biology and chemistry, but is that where her passion lies? Where does she want to travel? Is she a big fan of certain musicians, actors, directors, artists, writers, etc. Don’t dwell too much on the family stuff, just try to get her to open up about things she wants to talk about. I get the feeling that with family playing such a huge role in her life, and in your potential dating future, that’s the one topic she’ll want to avoid. Don’t try to force the conversation one way, just follow the flow. If you bring up travel and she says she doesn’t want to travel, don’t keep asking about travel. If you bring up travel and she focuses in on a specific city, or a specific reason to travel, follow that conversation thread.

The “donts” you want to avoid change from person to person but I would say to avoid politics, talk about dating and exes, and generally controversial conversation topics. Avoid asking questions that can only be responded to with answers of either Yes or No. You should also avoid discussing marriage, sex, your potential future together, anything like that. Keep the conversation light, but focus on getting to know her. If you sense that she doesn’t want to talk about a subject, don’t push it, and specifically in your case, don’t discuss anything that you wouldn’t want repeated to her family since her brother is there with you watching you LIKE A HAWK.

As for what to wear, completely up to you of course, but I’d avoid hats in general. Unless you’re dressing up and wearing a formal hat, or you’re wearing a hat as some sort of defense against the elements, (winter hats in the winter, hat with a brim because it’s sunny, etc.) avoid wearing hats on dates. Wearing hats and sunglasses on dates when you don’t need them gives off a vibe that you’re guarded, closed off, or hiding something (like a bald spot maybe). Since you’re going bowling feel free to dress casually, but the nicest version of casual you can. I’d probably wear neat looking jeans, a comfortable but nice sneakers (i.e. not my gross gym sneaker or running sneaker), and a shirt that is comfortable but looks good since I’m planning on doing some sort of physical activity. Remember, bowling involves movement, so wearing khaki’s and a shirt is fine if that’s your style, but I’d avoid tucking your shirt in. It’s going to constantly get untucked when bowling and it’ll make you look either sloppy, or fussy because you keep tucking it in. No clue what the weather is like near you, but a nice golf shirt, untucked, with khaki’s would be fine. Or a nice dress shirt, untucked with your sleeves rolled up.

As for general advice, well, just be yourself. People say that and it sounds trite, but seriously, don’t go out of your way to impress her, just be yourself and hope it impresses her. People respect and are attracted to people who are genuine, if they were ever going to be attracted to you at all. If she isn’t into you, pretending to be someone else isn’t going to change that. Try to show her a good time without coming across as desperate for marriage. I know that culturally, in the long-term it’s why you were set-up, but you don’t have to make it a point of the date. Just show her how fun a time she’ll have with you if she keeps going on dates with you.

Best of luck, Happy New Year, and…

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

One thought on “Unique first date, and I need advice!

Leave a Reply

Your email address will not be published.