What’s The Right Way To Ask Someone Out?

What's The Right Way To Ask Someone Out?


Hi Dr. NerdLove:

First of all, I’m really glad that I found you at a time when I decided to get out of my bubble and open myself to relationships and all other possibilities. I’m 22, and frankly, I haven’t dated before. I realize I was in a cocoon for so long, and I’m from a different culture altogether than the usual viewer here. Thinking of it, that’s not an excuse as to why I haven’t dated before. Let’s just say, I wasn’t in a right frame of mind, always inside my head, dealing with my own insecurities, needless to say, overthinking about things. Hey, that’s how I guess you set yourself to be in academia, overthinking.

Now to my question, I’m basically starting from scratch and would some of the things to be explicated. Actually, there’s this girl in my class with whom I hang out with sometime, and I don’t how should I go about asking her. Thing is, spending some time with her I have caught up some feelings, and I think I should put myself out there without any delay. Should I just say, “let’s grab a coffee yada yada yada”, or should I explicitly say that I want to take her out on a date. I don’t want to use the term “friendzone”, but I suspect that may be the case here. I mean when I want to ask her out, I want to let her know that this is for something romantic, and not the usual hang out. That’s the reason I asked whether or not I should use the word “date” explicitly.

Adding to this, I think I’m prepared to take a no for an answer too, so it’s not like I’d flake or anything. I mean, I’d be bit hurt if she says no, but that’s expected.

Second, I know you’ve written several articles, heck books on this, but I still want to ask “how do you avoid the Friend Zone“, but with a slightly variation. Suppose you meet someone or have a cool conversation with, or a cutie you’ve developed crush on and now that you’ve gone and talk to her, what should you do? Ask her for a date then and right there or just get her number and shoot off? And again, as with my previous question, when in fact you do ask her, should I you use the word “date” explicitly.

Sorry, if I’m being too blunt here, what do they say, brute force approach. I’m at a point zero with this thing, getting into it much later than many of my peers and I don’t know how should I approach it. There’s an element of regret on missing out and being uncool too. Like, hey sucker, look at those folks they’ve been banging out since teenage and here you’re at 22 having never been there. I don’t know how to deal this with feeling.

This is all I have to ask and say, I love what you’re doing and we very much need a positive and level headed presence like you in the internet.


First Time Jitters

This one’s easy FTJ: you use your words. One of the most common reasons why dating can seem so fraught and confusing is because everyone is doing their damndest to not say what they want. They hint, they suggest, they imply or they simply hope the other person divines what they’re trying to do… but they won’t actually come out and say what they want in clear and concise terms.

Part of the problem is that we all have a tendency to assume that our communication style is the default. Some folks may think that their behavior clearly sends a message — “here, I am showing you how much I like you” or “I will demonstrate my support for you by doing X, Y or Z for you” — but the other person doesn’t receive it that way. So while one person may be shouting “love” as loudly as possible, the other person doesn’t hear it because they need to actually hear the words spoken out loud instead of implied by behavior.

As a result, you get a lot of folks who get very different messages about what’s going on. And occasionally those messages can confuse what would seem like an otherwise clearcut and simple situation. Such as, say, being romantically interested in someone and wanting to ask them out on a date.

Now to be fair, some folks — mostly people who either know their crush doesn’t return their feelings or who want to avoid any chance of rejection — will rely on that ambiguity. They’ll ask somebody out and decide based on how things are going whether it’s a date or not. Or they’ll ask them out with so much plausible deniability that the other person may be surprised to find out that the other person sees it as a date. Those moments can leave the other person feeling tricked or manipulated, even if they like them. So my overall advice when it comes to asking people on dates is to be as clear as possible.

In your case, FTJ, you’ve got a friend who may well not realize that you’re into her. If you were to say “hey, let’s go get coffee,” she may well think that you’re asking her grab coffee as friends. After all, this is a thing that friends do — go have a drink and hang out to chat, especially after class. This, needless to say, would be counterproductive to your overall goals. Doubly so if you two aren’t flirting or otherwise signaling to one another that you’re interested in each other as more than platonic friends.

What I would suggest is to just tell her that you’d like to take her on a date. That is, suggest a specific activity at a specific place and time — “Hey, I’m going to this gallery opening next weekend and I think you’d really like it. If you’re interested, I’d love to take you out on a date to go see it.” Giving a specific activity, rather than something more vague — “hang out some time” or “get together” — not only means that she understands what you’re asking, but you’re giving her a specific thing to say yes or no to. This means that she now has the opportunity to decide whether she feels the same way and — crucially — if she wants to go on this particular date with you.

Specificity is incredibly helpful here. Suggesting a specific activity means that she can set expectations and preparations appropriately — will there be lots of walking or standing around? What activity level will it be? It also gives her a chance to say “I can’t that day, but I’d love to do X on Y day instead,” rather than leaving things up in the air as to what you’ll be doing and how much time it’ll take.

The most important thing, however, is not to be down on yourself about being a late bloomer. The fact that other people may have more experience or started earlier than you has absolutely no bearing on you as a person. You’re not in competition with anyone, nor are you starting out too late. You’re on your own journey and you’ve been making the best decisions you could with the information you had at the time. Now that circumstances have changed and the information you have has changed, you’re making different decisions and that’s just fine.

So let go of that feeling that you’re a loser. The very fact that you’re stepping up to the metaphorical plate should tell you that you’re not. You’re doing a thing that you find scary and intimidating — asking your crush out on a date. That’s brave of you. That’s awesome. You’re taking steps to change your life and move it in the direction you want. It doesn’t matter when you started; it just matters that you’re doing it.

And hey, if she isn’t into you? That’s fine too. All it means is that you and she weren’t right for one another and you’re one step closer to finding the person who is.

Good luck.

Dear Dr. NerdLove,

Warning: this one’s a doozy.

I’ve been living with my boyfriend for almost 2 years, (we have been together for almost 3). Initially, we were stupidly in love; I’d never felt that way about anyone and was certain he was “The One.” Once we moved in together, (I was told I had to move out of where I was staying as the landlord was selling), things started to change, as I’d expected they would. I struggled to adapt to his way of doing things. He has, in my opinion, too many animals, (two of which I’m allergic to). He is not as clean as I am, is incredibly stubborn, and doesn’t follow through with what he promises. However, he is supportive and has helped me deal with many difficult things over the past two years. I appreciate him for that, but also feel indebted. He is the first “stable” person I’ve dated- in other words, the first non-addict.

The past year, I’ve been plugging along, pretty underwhelmed and frustrated, but I’ve come to not trust my own choices regarding men — so I have been giving ultimatums rather than breaking things off. (I know this is a problem in and of itself.)

By September, 2021, my boyfriend and I had been working on many aspects of the relationship with nothing to really show for it. Then I got a phone call.

My ex boyfriend/friend since we were 12 called me to tell me he had just gotten out of rehab.

We dated long distance 7 years ago, and it was not the prettiest breakup. From my point of view, he was dealing with undiagnosed/unrecognized alcoholism, depression, and anxiety… and the distance had worn us both down as neither could move to be with the other. Three years after our breakup, he was in a new serious relationship and developed a drug addiction. We did not speak during this time, which I assumed was due to his insecure girlfriend. (I was not aware he was using until a year ago.)

In September, we began having the most sincere, honest conversations we have ever had. I went to his city to visit, (where my best friend also lives), and it was incredible seeing him. I just wanted to hold him as I felt like I had lost him. Now that he is back in my life, I feel alive and understood again for the first time in years. We talk every day and I know/he tells me that he loves me. We have made good all of our unresolved feelings from our relationship years ago. Because we have both had a rough few years, we also see things differently than we did before, (coincidentally in the same way). He is on his way to becoming his best self; I can feel it and it is incredibly attractive to me. He has stayed sober since August. We are still states away. I am still in a relationship.

He wants to meet up with me in a month.

I honestly love him, but I am terrified — first and foremost, that this could in any way interfere with his sobriety journey. (This topic, to be clear, has been discussed repeatedly.)

I’m also hating myself for having feelings for someone other than my partner. I also don’t trust my judgment.

In a perfect world, my ex and I would be together. We would already have a family by now. We would have made things work years ago and he would have gotten the help he needed long ago, before his addiction morphed into something crazier. “Would have.” I don’t think it’s impossible now, but I know it’s not likely considering our circumstances.

I want to see him, but I don’t feel comfortable crossing lines while in a relationship, (he would be fine with this). I don’t ever lie, but for some reason I’m considering lying about where I go while I go to visit with my ex. A part of me feels like I need it so badly; I’m unfamiliar with the feeling, actually.

I am afraid of breaking up with my current boyfriend because I’m concerned that I’m not thinking straight. I feel like I owe it to him to try harder to make things work/give things more time. My ex is aware of all of my feelings and i am not promising him anything I cannot deliver. If I could guarantee that my ex and I would live happily ever after, I would cut my losses- but there is no guarantee.

I have a million questions, but for your and everyone else’s sake: Should I or should I not go to visit with my ex? Do I tell my boyfriend, honestly, how I am feeling and where I would be going? What is the matter with me/why can’t I make a choice? Any other insight is appreciated as well.


Stuck, Sad, but Grateful

The first thing I want to say, SSG, is that I think you’ve given yourself a false binary here. This isn’t a case of “do you continue seeing your current beau or go back to your ex.” You have two very separate choices. First is whether or not you should stay with your current boyfriend. The second is whether you should pursue something with your ex. The answer to one doesn’t necessarily dictate the answer to the other, and treating the two as being inextricable from one another just adds layers of complications that only serve to make things more confusing.

The first question — should you stay with your current boyfriend — is a tough one. He may be the most stable person you’ve dated and the first non-addict, but that doesn’t mean that he’s right for you. He can be stable and in a good place but still be incompatible with you. The stability and support may be a plus, but the other issues — the conflict over animals, the lack of follow-through with his promises, the difference in cleanliness — could well be potential dealbreakers for you. That’s something you should be considering for its own sake, not in the context of your newly clean and sober ex.

The second question — should you pursue something with your ex — is equally tricky. One of the reasons why it can be hard to get over someone is that they represent something to you beyond the person involved. A toxic ex — or an addict, for that matter — can be exciting. They may not be a good person, but the drama, tension and excitement can be surprisingly heady and compelling, even if you don’t actually enjoy it.

There’s also the classic question of “should you get back with him”? Just because you miss him and still have feelings for him doesn’t necessarily mean that the relationship will be any better the second time around. I believe that, before getting back with an ex, you need to answer 5 questions:

Question #1: Why did you break up in the first place?

Question #2: Has the reason why you broke up changed?

Question #3: Why Now?

Question #4: Do you miss THEM, or do you miss what they represent?

Question #5: Are they right for you, NOW?

It’s important to think about these questions very carefully. If, for example, the reasons why you broke up haven’t changed — or haven’t changed enough — then all you’re doing is setting yourselves up for Break Up 2: Electric Boogaloo and nobody likes a sequel that’s just the first story over again but somehow worse. Similarly, are you thinking about him purely because of the nostalgia and your frustration with your current boyfriend? Would you be feeling this strongly if you didn’t have your current relationship to serve as contrast to the possibility — and it’s only a possibility right now — of what you might have with your ex?

Now, it sounds like you’ve answered at least some of these questions. You’ve discussed your previous relationship, you’ve talked about your problems and aired out your grievances with one another. He’s in a better place in life than he was. However, he’s still in another state and his journey to sobriety is still fairly fresh; you’re understandably worried that being back together might throw him back into old patterns. That’s a very real and legitimate concern.

However, there’s also the fact that you’re still pining for what you used to have, rather than what you might have with him as he is now. Nostalgia can be a trap; time can have a way of blurring the sharp edges of the past and obscuring the end of the relationship while applying a golden filter to the early days. While there’s a lot of you old boyfriend still there, he’s fundamentally a different person, and those differences may mean the two of you won’t be compatible this time around.

So here’s my advice: consider these two questions entirely separately. Start with deciding whether or not you’re going to stay with your current boyfriend. Stability and support are important, but they’re not the only qualities you need in a partner. You need serious, deep compatibility for a long-term relationship — compatibility on core values, not just liking the same TV shows or music. It sounds like you feel like you owe him more than you have a deep and abiding love for him.

After you resolve that question, do some serious thinking about your ex. Answer those 5 questions to the best of your ability — especially considering the fact that you’d still be a long-distance relationship. If — and this is a mighty big if — you think you and he could make another go of it, I would suggest taking things slowly. Yes, you and he have history, but it’s been years and he’s had some pretty major life changes in the interim. It’s going to be important to try to see this as starting a new relationship with him, not resuming an old one. Meeting him as who he is now is important; otherwise you run the risk of falling back into old patterns, which could be bad for the both of you.

I know he excites you, but you’ve got the time to take things slowly. He’s not going anywhere and neither are you.

Good luck.