Do you have a guy you’ve been friends with for a while and you feel it’s time to take it to the next level? Or maybe you’ve been casually dating around and have finally found the guy you want to commit to. This ultimate guide to how to ask him to be your boyfriend will give you everything you need to make it happen.
Whether you’re 16 or 66, no matter how confident you are, this task can be slightly daunting.
From preparation, to date ideas, to dealing with the answer. Follow this step-by-step guide to get all the jitters out and go get the guy:
1. Are You Both Ready?
Before you figure out how to ask him to be your boyfriend, the first thing you need to do is decide if you are both ready for a relationship.
Even if you like each other, if one or both of you aren’t emotionally, mentally, or physically ready to be in a committed relationship, it’s going to do more harm than good.
Consider these questions, in order, to decide if you’re ready…
Do you really like him?
If he never changed from who is he now, for better or for worse, would you be able to have a relationship with him long term?
Are there any “deal breakers” or red flags that you think you can change?
You probably can’t change anything major about his personality, so if you cant’ accept the good and the bad now, you might want to consider if he’s worth it.
You’ll be dating who he is at this moment, not who he may or may not be in the future.
Are you ready for a relationship?
Is your “relationship wanderlust” over and can you commit to one person for a while, possibly forever?
Do you have any baggage that is better dealt with outside of a relationship?
These are things like unresolved feelings for another person, a history of being sexually assaulted, or mental health issues you haven’t sought treatment for yet.
Do you communicate well? Can you apologize for your mistakes and make efforts to change them?
Can you express and deal with anger and disappointment in a calm way while telling your partner what you need from them?
Do you have the time for a relationship? It’s OK to be independent and need some time for yourself.
But are you so busy with work, school, life, family, or other things that you won’t be able to make as much for a boyfriend as you should, or will doing so stress you out?
Is he worthy of you?
Does he treat you well and does he respect you? This isn’t a matter of chivalry, it’s about valuing you as a person and not thinking any less of you because you’re a woman.
Does he make you a better person, or a worse person? Does he encourage you to be the best person you can be, praise your strengths, and help you overcome your weaknesses?
Or does he bring out the worst of you, encourage bad behaviors, and make you feel badly about how you think or act?
Do your friends and family approve of him?
Our friends and family usually want what’s best for us.
Do they support your friendship with this guy, or do they overwhelmingly dislike this him and can give you reasons why?
Has he met your friends and family, and does he generally get along with them?
Am I fine being single?
Are you getting in a relationship just for the sake of being in a relationship? Would you be fine if you had to remain single?
Do you want a relationship with him or just a relationship, in general?
People are happiest in a relationship when they’re able to function fine single — it means you’re happy with who you are as a person, and that makes a difference.
2. Test The Waters: Ask Him About The Future First
Test the waters first, both by seeing if he’s even thought of the future and if there’s any signs that he likes you. Try to figure out the following…
What are his hopes and dreams?
If he’s relatively ambitious, you can tell a lot by what he’s working toward.
If he works hard, that’s great, but not if it’s going to prevent him from spending the time he needs to with his future family.
Lacking ambition doesn’t have to be a deal-breaker either, just make sure he has some other great qualities — no one wants to date an eternal couch potato!
What are his fears?
Does he have a fear of commitment? Is he terrified of becoming a father someday or doesn’t think he’ll be a good husband?
These don’t need to prevent you from going out with him, people can overcome their fears, but you need to know what you’re in for if you’re able to!
It might seem a bit early to ask all this, but you can do it subtly, and it may save you some time and heart break if you don’t like the answers.
Is he potentially interested in you?
You’re probably already looking for signs if he likes you or not, and it’s probably going to be the biggest reason you decide whether to ask him to commit.
It probably makes you feel like you’re in middle school. Welcome to relationships.
To figure out if he likes you, look for these signs…
Does he talk about a future with you without you asking?
He’d be using phrases like “Next year we can…” or “I want to take you there some day,” or “you’ll have to meet my great aunt Ruth someday, she’s hilarious.”
This shows he’s thinking about a future with you in it.
Does he text you randomly, and do you have inside jokes?
This means that he’s thinking about you even when you’re not around, and you’re developing your own unique identity as friends and as a couple.
Does he speak well of you to other people and defend you when people speak poorly about you?
He obviously thinks highly of you and cares about what other people think. He’s protective of you!
Do you have fun together?
No one wants a boring partner. It doesn’t matter what you consider fun to be, as long as you can have it together.
Does he go out of his way to spend time with you?
He’s making you a priority in his life regardless of what else he has going on in his busy life.
He may just value your friendship, but chances are he considers you an essential part of his life.
Is he “always there” for you?
This might just make him a good friend. But it makes for excellent boyfriend material and if he’s in, he’ll be “all in.”
Does he care about how you’re doing?
He cares for you on some level and wants you to be happy.
Sometimes men might be on the fence, or too scared to be the one initiate the conversation. Sometimes we’re just oblivious.
If they care about you and realize that you want a relationship, that can make all the difference.
3. Determine His Communication Style
When you’re figuring out how to ask him to be your boyfriend, consider his communication style. It will help you decide the best possible way to ask him.
Is he quiet or talkative?
If he’s more on the talkative side, you might want to go on a nice long walk or a dinner before you ask him, so you can have an intimacy-building conversation.
If he’s on the quieter side, consider a movie or game night when you ask him. These aren’t necessarily dates, they’re just hanging out, so it doesn’t have to be anything fancy.
Does he need time to process or does he wear his emotions on his sleeve?
If he needs time to process, don’t ask him in a public or surprising way.
If he’s very transparent about his emotions, or can process them quickly, you could ask him in a way that might go viral.
If he’s serious, you can take him out for a non-romantic date, or maybe even attend a lecture or visit a museum.
If he’s a jokester, consider pulling a prank on him to ask him — he’ll never forget it and it might even endear you to him even more!
Another reason to gauge his communication style is to make sure you’re compatible and able to be in a relationship with each other.
Communication is so key to a relationship that it is one of the primary deciding factors of how long a relationship will last.
I’m not saying to start a fight with him. But if you haven’t fought before, how are you going to know if you can get through it?
If you haven’t fought, you’re probably not that intimate with each other yet — but you’ll get your chance eventually.
Can you both apologize?
Can you stay calm even if you’re angry? Find it easy to express that you care about each other, even if you might not want to be around the person at the moment?
All of these are signs of good communication styles and shows that your commitment goes beyond how you feel about the person during the fight.
4. Preparing Yourself For His Response
Even if you’re pretty confident he likes you, there’s still a small chance he’ll say no (don’t let that psych you out though).
Whether he says yes or no, you should prepare yourself for the answer.
I’ll talk about what do if he says yes. But for now, grab the ice cream and start preparing for what happens if he says no.
If he says no, will you still be friends with him?
Whether you choose to cut him out of your life or still want him in it, it will likely be painful.
Either decision is going to be hard. Sometimes you can’t move on unless you completely stop seeing each other.
Still, if you can move on while still seeing him as a friend, you won’t lose a valuable friend and your relationship can grow and blossom in a way you maybe didn’t expect.
Perhaps the best solution, if you’re strong enough to handle it, is take a break for a couple months and then start being friends again.
Who will you lean on for support if he says no?
It’s good to have a support group of some kind — someone who can sit with you in your sweatpants, eat ice cream, and watch Bridget Jones’ Diary.
Girlfriends, a mom or aunt, even a different close guy friend can provide the support you need.
Even if you don’t have any close friends who can do this for you (you should find some), maybe there’s an online group, a phone support number, or a professional counselor you can talk with.
Just make sure you find someone. No matter how big or small the rejection, you shouldn’t have to do this alone.
Get your coping mechanisms ready, just in case.
Whether it’s the thrill of pommeling a punching bag, indulging in sappy romantic movies, or eating a pound of chocolate, you probably have some tried and true methods of dealing with heartache.
Stock up, rent all the movies, and get that gym membership, just in case things don’t go your way.
5. Plan Your Approach
What approach do you want to take? Public or private? Romantic or silly? Classic or New? It will all depend on your personalities and the type of relationship you have.
Either way, don’t do it over a phone call, text, or email, even if you’re long distance.
If you’re out of ideas about how to ask him to be your boyfriend, try these ideas.
These are just a few of many, but they offer a wide arrange of possibilities for all personalities and interests…
A. Prom Date Proposal
This is the classic high school “ask him to be your prom date,” but you don’t have to be a teenager to think this is a cool idea.
Make a cute sign with some quippy saying like “Be Mine” or just “Will You Be My Boyfriend,” and have your friends lure him to a public place.
Things like this go viral, and it really puts the person on the spot. If they say no, it’s even more embarrassing for everyone involved.
Still, if they say yes, it’s something you and your friends and family will remember for the rest of your life and it will be a story you tell your future children and grandkids.
B. Walk in the Park
A nice relaxing walk in the park can set the perfect atmosphere for popping the boyfriend question.
It’s not too much of a date, and the fresh air and nature can calm any nerves you have.
It’s a nice mix of public and private, and you can both go your separate ways easily if things don’t go the way you want. Have a stroll, sit on a bench and chat, and take it from there!
C. First Date Hook
Fishing can be incredibly calming and a nice intimate experience.
If your prospective boyfriend is a man of few words, and outdoorsy, this could be the perfect way to ask him.
If you’re super confident he’ll say yes, you can fish from the boat, otherwise stay on the dock so you can leave if things don’t go your way.
D. Spicing Up the Kitchen
If you’re casually dating but are looking to make it more official, try taking a cooking class together, or making a meal together at your home.
Cooking together can be fun & intimate and can build some quality memories together. You can get to know each other’s tastes and styles through it.
Leave the conversation until after dinner however, even though you might not want to wait that long; it will make it less awkward if he doesn’t reciprocate your feelings.
E. Jumbo Screen Announcement
This one is super cliché, but can be very endearing, especially for a guy who likes sports or a lot of attention.
If you go to a sports game with him (baseball usually works best for this, but any sporting event can do it), instead of the usual “will you marry me,” you can ask “will you be my boyfriend?”
It’ll be super cute, but it will also put him on the spot and potentially make him feel like he has to say yes.
Make sure you’ve talked about being more serious beforehand, and that he doesn’t mind being the center of attention, before you do this.
F. Heart to Heart
If your prospective boyfriend is the type who likes quality conversation or really just being one on one with you, consider just having a heart-to-heart with him.
It doesn’t matter where, or what you do, but it’ll probably be over dinner, a walk, or one of these other ideas.
G. Home Movie Night
For a less intimidating night, or one in which you don’t have to carry on a conversation most of the time, consider having a movie night.
It doesn’t have to be a romantic movie — it could be comedy, action, or if you’re looking for an excuse to be held, horror.
The point of this is that you can have fun together without the burden of a heavy or prolonged conversation.
After the movie, you can tell him you had fun and then launch into the conversation.
It’s possible you’ll spend the whole movie running through what you want to say, and that’s OK. He’ll get to spend time with you in a low-pressure situation.
H. Musical Fun
Going dancing can be very fun, and a way to set the romantic mood before asking him to be your boyfriend.
It’s fast-paced, releases endorphins, and is a great reason for physical touch.
You can bet the pump will be primed if you go this way, but it probably works best if you already have a causal dating relationship. Ask your “friend” to go dancing may freak him out.
Another option which is just as fun but less intimidating as far as romance goes, is to go out for karaoke.
You can have a few drinks (stay sober though) to loosen yourself up for the conversation, and you can see each other having lots of fun.
Maybe you can even sing a song together, or you can dedicate a song to him to break the dating ice.
I. Dine and Dash
I’m not advocating you run out on a check, just that you have a quick meal over a casual conversation.
This can be a good option if you’re both busy professionals or if you want to have a “quick out” if you don’t get the answer you’re looking for.
You can meet for lunch, or even dinner, at a café or coffee shop.
Keep the conversation mostly casual but tell him you are ready for an exclusive relationship and are hoping he is too.
This is a great method for a guy who needs a more casual approach to dating, or who prefers to remain “business-minded” even in relationships.
J. Cultural Broadening
Experiencing culture can be an amazing segue into asking for an exclusive relationship, plus it can be fun for certain personality types.
Visiting a museum, antique shopping, or even spending the day in the library can help you build on mutual interests and give you a connection you can talk about.
After the “date” you can say “I want to experience so much more with you” and launch into your conversation about making him your boyfriend!
K. Urban Adventure
If you live in or near the city, it’s likely you’ve never really explored all it has to offer. Spend a day seeing a some of the tourist attractions locals never visit.
It can be a cool little discovery for you both, give you something to talk about, and establish some memories.
You might even find “your place” that defines you as a couple. This is another option that provides an easy escape should you need a quick getaway.
6. The Delivery
When you’re figuring out how to ask him to be your boyfriend, the biggest thing to consider is what you’ll actually say to him.
You could plan the perfect set-up, know he’s right for you, and be emotionally prepared, but if you flub the delivery it’ll be hard for you to get your point across.
Follow these steps for a nice progression to the conversation.
It builds nicely on all its previous points and should give him the best possible chance of saying he does want to be your boyfriend…
1. Tell him everything you like about him.
This is buttering him up and letting him know how you feel without actually having to be explicit about it yet.
It’s likely he’s going to get the hint that something is up, but hopefully he lets you finish.
You may want to say beforehand “I have something I need to tell you, and I don’t want you to interrupt me until I’m done.”
If you have to do that to soothe your nerves and make sure you get everything out, that’s fine. Otherwise, allowing him to interrupt you could bring about some great conversation.
It’s all about what you feel comfortable with!
2. Tell him how you feel when you’re with him, and how he’s made your life better.
This helps him see, from your perspective, why you want to be in a relationship with him.
It also continues to affirm him by telling him how the things you like about him make your life better.
You can tell him things like “I really appreciate how you’re always there for me, and it’s been really great to have your support this year.”
Or you can say “I love you always make me laugh, it keeps me positive and looking on the brighter side of life,” or “you really make me want to be the best possible version of myself.”
It’s probably going to get a little cheesy, and if he doesn’t do well with too many compliments, you can keep it vague and just tell him you’re so grateful for his presence in your life.
The “jig” is probably up here, and he’s going to know where it’s leading. That’s OK. Say what you have to say and don’t worry about his response until he gives it.
This is where you’ll probably start to see some really obvious body language. He might grab your hand and make eye contact while you talk.
Or he may lean back, cross his arms, and avoid eye contact. Either way, keep going and finish what you have to say. You deserve to say it and he deserves to know it!
3. Tell him what you want for him in a relationship.
This is where you connect what he’s done for you, and your good qualities, with what you want to do for him in a relationship.
You can say things like “I want to make you laugh,” or “I hope I can help you look at life just as positively as you help me to,” or “I want to be there for you whenever you need support.”
This builds on the previous part of the conversation. But it also lets him know that you want the best for him, and that you want to reciprocate what he does for you.
In many ways, it sets early expectation for what you want the relationship to look like. It can help make the relationship look very appealing if he’s still on the fence.
4. Ask him to officially be your boyfriend.
This could take a few different forms — “Will you let me be your girlfriend,” “I want you to be my boyfriend,” or “let’s see each other exclusively” are options.
But this is the point where you’re explicit about what you want, and you wait for his answer…
This conversation is going to vary based on how each of you communicate, your personalities, and what exactly you’re looking for in a relationship.
The above examples are rather intense and are probably best for people who have been friends or casually dating for a while.
While the format includes everything you need, you can change it up, make it more casual, or even insert some comedy to personalize it.
One thing that might help is writing down everything you want to say on note cards or on your smartphone.
You probably won’t (and shouldn’t) use it while you’re actually having the conversation. But the act of writing will help you remember what you actually want to say when the time comes.
7. Moving Forward
Once you hear his response, you can decide how to deal with it, one way or another.
If he says yes.
Congratulations! Celebrate by going on a nice, official date as an exclusive couple.
It doesn’t have to be right away, but you will want to establish some boundaries and expectations — how fast you want to move, just how serious this is, and what you both want out of the relationship.
Also, make sure you announce it to your friends and family that you are officially together.
Relationships are more likely to succeed when you have friends and family supporting you. Enjoy your new relationship and make the most of it!
If he says no.
You basically have two options — cut him out so you can move on or try to maintain a friendship. Don’t make the decision right away.
Take a few days or a week to grieve (using all your coping mechanisms we talked about), and then try to make the decision with a clear head.
If you decide you want to still be friends with him, which I very much encourage, as long as you can still move on while being friends, you’ll need to set some very clear boundaries about how what that friendship looks like.
Planning how to ask him to be your boyfriend can make even the most confident woman a little nervous at times.
Even if you have all the evidence that he’s into you, it’s perfectly natural to still have a bit of doubt. But slay that fear!
Using this step-by-step guide, you should have all the tools you need to plan, prepare, deliver, and deal with asking him to be your boyfriend. Now go get your guy!