I got drunk and asked my roommate on a date. What do I do?


Brittlenot1 asks: 

I’m a 23-year-old male, I’ve been living with 3 other roommates my age for the past 6 months. One of the roommates moved out to be with family, so we invited a friend of ours to take his room. This “friend” I have only known for about 2 months, and we’ve only hung out on maybe 2 occasions. She is a shy girl, but has stated that “once I open up, I can be random and goofy.” She’s attractive, and I would really like to get to know her more, and perhaps form a relationship if the feelings are mutual. Well, last night, I got really drunk with my other roommates, she was aware that I was trashed. I then got on Facebook, and messaged her, asking if she would let me take her out to eat so that we could get to know each other better. The next morning, after realizing what a stupidly embarrassing thing I had just done, I had messaged her asking her to ignore what I sent, laughing it off at my expense to ease the awkwardness.

To my surprise, she replied saying that she has never been to the restaurant that I had mentioned in my drunk message. This totally caught me off guard, as I am a very shy introvert, I’m not terrible looking, but due to past relationships, I have not asked a girl on a date in over 6 years, any relationship I had between then and now, has been with girls asking me. So, needless to say, I got myself in over my head, I am extremely nervous, and I’m not sure what I can do to ensure that I don’t ruin this date, and that I can hopefully get a second one. The drive to the restaurant is a good 15 minutes, and we’ve never really talked about ourselves to each other, what should we talk about? I want her to feel comfortable around me so that she can open up to me. And I have no idea what to say to her during dinner other than asking about her.

I’m not desperate by any means, it’s just that I’ve met a girl I believe I could see myself happy with (for once) and I don’t want to mess it up.

Any tips?

Demetrius says:

Man, this is just such a bad idea on so many levels. I might just be a pessimist (or more likely a pragmatist) but dating your roommate is such a terrible idea. The fact that even before you drunkenly asked her out you thought it would be a good idea to get to know her and form a romantic relationship is such a terrible, terrible idea. I know that the idea of a live-in partner is awesome on a lot of levels, one of which is the whole “it’s super easy to sleep with someone if they live a few feet away” but you have to remember, some relationships fail. By some, I mean most. The difference is, usually you aren’t stuck living with someone after you break things off. If you were asking me whether or not you should date your roommate, the answer would be no. If you really are as shy and introverted as you say, I doubt having to live with your ex is going to be all that comfortable. *Sigh* Since you’ve already asked your roommate on a date, I guess we’ll have to tackle this.

Right off the bat I want to say, you have to go through with this dinner. The good news is that this doesn’t necessarily need to be a romantic date. The fact is, you asked your roommate to grab dinner with you while drunk. Not go on a date, but to grab dinner to get to know each other better. Yes, that could be a date but it could also be a time for roommates to get to know each other better, platonically. I want to make this crystal clear: I do not recommend that you pursue your roommate romantically. With that said, I feel like you’re dead set on this. Regardless of what you decide to do, don’t go into dinner with a mindset that this has to be a date. Instead, approach it as what it is, dinner with a roommate. Trust me on this, if you take the pressure off, things will go a whole lot smoother.

As for what to talk about, trust me when I say that it’s simpler and easier then you might think. Maybe it’s because of your introversion, or shyness, or your attraction to her, but trust me when I tell you that conversations aren’t that hard. If you’re an anxious person, or if you’re painfully introverted, you might feel like conversations are difficult, but really its individual people who make conversations difficult. Get people to start talking about themselves and you’ll find that conversation will flow. Encountering people who aren’t responsive to polite conversation isn’t a sign that you’re bad at conversation so much as it’s a sign that the don’t want to talk to you. If you keep your conversation light, using the FORD method (Family, Occupation, Recreation, Dreams) you can be assured that at a minimum, your conversation will be pretty good. The conversation should also bounce back and forth, even if you have to steer it a bit. If you ask her what she does for a living and she doesn’t follow-up with a question about your occupation, pretend she did by saying “Oh that’s cool. I work as a {insert your occupation} and I really enjoy this part of my job”. Your nerves and shyness are mostly out of your control, but you can control what you do and say. Keep the conversation light, don’t imply that you’re on a romantic date, and take things one step at a time. Again, I don’t recommend that you pursue your roommate romantically,but if you plan on doing it, you first need to figure out if you’re compatible. If you keep conversation light and get to know her, the more important compatibility stuff will come up naturally.

Good Luck Out There.

6 thoughts on “I got drunk and asked my roommate on a date. What do I do?

  1. For once I don’t agree with Dem wholeheartedly. Look, you do need to be careful the roomate thing could get messy. But like they say ‘in vino veritas’…so you like her, she seems to like you. Be brave, take her out to dinner. Don’t come on to strong but let things grow organically if they are destined too.

    Dem, We’d love your opinion on this post : https://rinsebeforeuse.wordpress.com/2015/11/19/shameless-in-love/

    Liked by 1 person

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