By elimination, dishonesty is the second-best policy. -George Carlin
Question #92547 posted on 09/02/2019 10:36 p.m.

To the wizened sages of the internet,

How do I know when I should start dating a girl - like, when we should become boyfriend/girlfriend? There is a girl I'm really good friends with and she definitely likes me, but I'm kind of afraid to ask her on a date because I don't know where things will end up. Meanwhile I also enjoy going on dates with various random girls every few weeks but I'm not sure when is the time to start going on more 2nd, 3rd, 4th dates.

Do you have personal experiences on going from the "casual dating" phase to the "I should be in a relationship now" phase?

- another dating question


Dear friend, 

Your life will become much more enjoyable when you learn to worry less! Everything will work out. Ask the girls that you like spending time with on more dates. Most people are nice. 

Definitely ask out the girl you're sure likes you. If it doesn't work out long term, there won't be any severe consequences, and you can stay friends. First dates are very low-key, generally. If you enjoy it, tell her so. You know, the old, "Hey I had a lot of fun, we should do this again sometime. Are you free next Saturday for breakfast?" thing. If it's been a while since you went out with a girl, but want to ask her again, pop in with the, "I know it's been a while, but I had a good time on our last date and was wondering if you would be interested in _____?" 

As far as moving from casual dating to relationship phase... that's different for everyone, in my opinion. That isn't super helpful, but it really is a matter of feeling it out. I think Pebble and I went on like... maybe 2 official date-dates before he kissed me and we declared it official... but we also spent like several months of nearly every day just going on walks and talking and talking and talking and talking, and I knew I liked him. 

I think it's safe to say that if you want to be spending your time with only one specific girl, you should probably talk to her about your feelings and see what she's thinking, and move from there. It's hard to tell you exactly what to do, because there are billions of potential scenarios, and you can only do what you feel best about. As long as you do your job at communicating and being open and receptive to her feelings, things will probably be okay. 

Wow Guesthouse, you're so helpful *rolls eyes* 

But really. Don't be ashamed to ask girls on more than one date if you liked their company. If you start noticing you like hanging out with one more than the rest, ask her more often and move from there. You'll know when it feels right.




Dear Dater,

I agree with Guesthouse on asking the girl you have a crush on out. You need to start somewhere! 

When it comes to the DTR, it also varies from each potential couple. Some people like taking it slow, while others can move much faster. Carl and I made excuses to see each other every day while we were getting to know each other / newly dating. (I'd say that's a good sign for moving towards a relationship.) Another thing that was a breath of fresh air was that we never did the, "He took 30 minutes to reply to my text so I'm going to wait 30 minutes to reply to his text." Relationships are hard enough, don't make it more difficult by playing mind games!

One game changer for me when deciding if Carl and I were going to become a couple was when I realized I didn't want to go on other dates with three other guys. I talked to Carl about these future dates and he admitted that we weren't official, so I could have gone on these dates without a problem. But that's when I decided that I would be wasting the guys' time and money if I went. So I cancelled all of them and they were grateful for my honesty. We were official in two weeks, and spent time with each other every day minus his birthday. 

Overall, communication is one of the most important things in a successful relationship. Try to pick up on verbal and non-verbal cues that help you figure out where she's at. She may (or may not) be wondering the same questions as you are. Try to naturally continue the conversation after the first date to see if she's interested in a second date. If you get a second date, repeat.

-Goldie Rose


Dear you,

So I feel like the "exclusively dating phase" like just kinda happens? I'm sorry that's not very useful, but I feel like you will naturally start spending more time with each other and not going on dates with other people. When discussing that takes place also depends on how both of you feel. For me it happened around date 4 and we had already kissed. But basically it just boils down to when clarification is needed. I'll give you a tip though: don't ever do that on the first date ever. 

Hope this helps!



Dear you,

I am becoming staunchly converted to these rules:

  • Become exclusive only when you don't want to go out with anyone else.
  • Regular cuddling and kissing is for exclusive couples. 

These rules are designed based off experiences I'd rather not detail, an unhealthy amount of podcasts, and from the opinions of some star power role-models. I don't judge anyone who thinks these are too restrictive. I have been that person up until this week recently. I definitely respect the different strokes for different folks, and I trust everyone to make good decisions for their life, and I know it doesn't work like this for everyo--nah, I can't do this. The truth is, I really believe these are good rules and everyone would benefit from them. I'm changing, and I'm glad. 

DON'T WORRY! just ask her out and have a good time. If she gets the wrong idea, just have an honest conversation. Have you ever noticed how much DOESN'T happen in dating because people are afraid of someone getting the wrong idea? Have you ever considered that what they're really afraid of is ONE solitary mildly uncomfortable conversation? In most cases, the worst thing that could happen is you say "Hey, this is exactly where I'm at. Just thought you should know." Hard to do. BUT IS IT? Not really. 

Go on 2rd, 3rth, and 4nd dates if that's what you want (provided they want to go with you). If you communicate along the way, and don't say lies with your face, you will be absolutely fine and so will they. 

If you're trying to decide on a life phase like "Oh, I'm just dating around right now" or "Shoot to kill, I'm looking for the One." I wouldn't stress too much about that either. I have a precise moment where I thought I had transitioned. Heavenly Father was like "Okay, you're dating to marry now. Take it seriously." and I was like "Ok, this is very serious I'm dating for keeps now yessir." But then literally NOTHING about my dating style changed. I think I just understood more about what my time is worth, and my purpose. I still "date around." The only thing that changed is that now the minute I realize he is not for me, I say goodbye. Which I realized, I should have been doing even when I thought I was just "casual dating." Turns out, Heavenly Father had been taking my life seriously THE WHOLE TIME surprise surprise. 

To sum up:

  • Ask her out!
  • Date a lot. 
  • If you sense that anyone is on the wrong page with you, stop and communicate!
  • We're all dating Casually but also none of us are. All relationships are casual until suddenly they're not. You don't have to pick a phase.



Dear Dating,

Okay, I'm about to say something crazy, but bear with me here: the time to go on more dates is when you want to go on more dates. You don't have to follow any pre-prescribed rules about timing or when to become exclusive--just do what you want to do. Dating is supposedly fun (although I know in reality it's often stressful and anxiety-inducing), but try to get out of your own head and just have fun. It's okay if things don't pan out in the long run, it's okay if you start dating and call it off after a few weeks, it's okay if you don't start dating for a while and then decide that actually you do want to date this woman, just live in the moment and do what you want. As long as you're not actively stringing people along when you don't remotely like them, you're probably fine.



Dear you,

I agree with what the other writers have said about not worrying so much about it, and going on dates as you feel like it. However, I'd also like to give you validation for worrying. It's one thing to write about how you just shouldn't worry about dating, and stop over thinking things, but quite another to actually practice it. I do believe it's still worth practicing, but it's also okay to have difficulty practicing it.