It does seem like a daunting task, and honestly terrifying. But there is a common thread somewhere right? You kind of know each other and it can’t be that hard to find a situation where you guys can talk. Yes, there is a great deal of fear in approaching someone, even if it isn’t the first time you’ve been at a party or a small group together. Although some things are worth waiting for, you can move things along. Get to know if this guy is a romantic daydream or actual long term relationship material in twelve moves.
1. How do you even know he’s going to make for good boyfriend material?
This question will make or break this whole process. You already know each other casually through group activities with friends, school or at work. Through your past interactions, you probably know the answer to this question already. If he’s a good friend it doesn’t always mean he’s going to be a good partner in terms of being your boyfriend. Ponder how you interact with him. Is he’s flirty with just you or is it just his personality? How does he treat his friends? Is he an organizer of events? Or is he more of a party crasher who will eat all the food? Either way, you know yourself best. You know who you click with and who annoys you. Don’t just pursue this guy just because he’s pretty or popular, but because you see some long term potential for a great friendship. That could lead to something more than a friend later.
2. How do you both interact in groups?
Is he a considerate friend? Plan an excursion with a small party of your mutual friends. Invite him along. Keep an eye on his behavior without being obvious. If you are usually shy, now is the time to break that habit. Just go for it. Take the initiative and plan something as a group. Be sure you are the one to invite your crush along, whether it is a concert festival, a weekend camping trip or just a visit to the mall. Be the one to call up everyone in your clique personally to invite them along. It might be off-putting if your crush found out you focused a little too much on him. If you live in a rural area, a night of camping and stargazing would be perfect. If you’re in the city, plan something really tourist-like that none of you has done before.
If you are in college you will most likely participate in some ice-breaker activities. Don't avoid these organized events on campus. Your crush just might be there. It will be fun and you’ll get to interact with everyone in a new way, even your crush.
3. Do you have shared interests?
Don’t change your own behavior to attract him. In the long term that’s a poor plan. Whatever relationship you build on that is going to fizzle. Having genuine interests that you both participate in is important. Since you know him already through mutual friends, ask him for help finding a movie trailer or a game online. If he's kind of an outdoor natural type, invite him to the farmer’s market to help you plan a meal for your roommate. If you have a mutual friend with a birthday coming up, ask him for advice on what to buy them. This is a good way to measure his response. Interacting like this is a fine way to figure out if he’s a good gift giver, if he’s thoughtful, even if he’s stingy.
4. Is he sociable? A loner?
Whether you are a pizza and Netflix type or a shop 'til you drop and get sushi type, make sure you are both like-minded in your habits. If he’s a frequent customer at your local big box electronics store or an addict at the Ralph Lauren flagship store, be sure you both have similar habits. If you do end up together, you don’t want it to end just because you bore each other to death over things you don’t share an interest in. It is true that opposites attract. Long term you want someone who not only tolerates your quirks but finds them endearing.
5. Do you share the same Values?
Sharing like minded values is an important aspect to any budding relationship. Think about issues that are important to you. Do you participate in on campus rallies? Or would you rather sign online petitions? Be sure that your potential mate is on board with the things that matter. If he’s ever wearing a “meninist” tee, just run and don’t look back. But if he’s expressed a positive interest in expanding the civil rights bill, that’s a keeper right there.
6. His Style.
This is a superficial aspect of a person, but it is something to consider. You don’t want to be introducing this person to your family if his idea of getting ready to meet your folks is just dumping water on his face and putting on a baseball cap. It’s pretty obvious what his personal style is since you probably see him almost every day at school or work. It doesn’t matter if you are a total preppy and he’s a bohemian. If he’s planning his look, it’s an indicator that he’s thoughtful about his appearance. That is something you want to monitor. It is a clue into his life away from the group, away from school or work where you know each other initially. It can be a good way to figure out if you are compatible.
7. His Work Ethic.
You may have had experience working with him in a group project already. If you and your other teammates had to do all the work, forget about him. If he’s lazy in the group, imagine what it’s going to be like if you have to plan a party for a mutual friend or a vacation together. You don’t want to be the one making all the decisions and doing all the planning. It’s exhausting and sooner or later you’ll break it off.
8. How Does He Treat Others?
You can measure the worth of someone by the way they treat another living being who cannot do anything for them. If he’s got a big soft spot when it comes to animals, he’s got a great heart. Perhaps suggest he meet you at the animal shelter to volunteer for the day. From feeding the animals to mopping the floor, this task will reveal to you who he really is. Some towns or schools open the public park to volunteers for a cleanup effort, invite a few friends to come and include him in your call list. If he loses his temper or grins and continues to do his assigned task, it’s pretty important to put people through their paces so you can see how they react.
9. Is He a Cheater?
Has he ever cheated on one of his past girlfriends? This is a tough one to figure out on your own. You probably want to avoid having a direct conversation about this with him. See if you can casually talk to one of your mutual friends about this. It is poor form to judge people with the old adage “once a cheater always a cheater” but past performance is a good indicator of future performance.
10. His Body Language
Once you’ve done a few hangouts outside of the group, gauge his attitude toward you. If it’s sketchy, he cancels plans, he’s stiff around you, understand that it might not be right. A crush can be crushed once you actually get some one-on-one time with each other. So if that’s the case, just stop calling him. If he was just nervous and really likes you, he’ll probably call to hang out again. If not, no worries. It wasn't meant to happen.
11. Ask Him Out!
If your solo casual hangouts were warm and easy, make the first move and ask him out on a real date. Make it a traditional date activity like dinner and a movie, so he knows you’re serious. Don’t just ask him what he’s doing after work the next day, make sure you are heard and understood.
12. The First Date
First dates are always going to be awkward. It’s just part of life. If you find yourself with him alone after all this time and you have conversations with ease, it’s pretty much a done deal. It’s just the cutest when a guy asks, “Want to be my girlfriend?”. But it’s even better when you know it’s right and you say it first. Be confident and know that if he says no, it’s no big deal. You still get to be friends and that’s pretty sweet.
Some Key Things to Consider
It seems like the time when you find someone of interest is when you aren’t looking for them. Focus on the things that make you happy. People seem to be drawn to other people who are enjoying life doing their own thing.
Be comfortable in your own skin before you pursue a relationship with anyone. This is a big hurdle to overcome. Whether it’s the very first attempt at a boyfriend or you’re just getting out of a long-term relationship, think about why you are having feelings for someone new.
A rebound relationship is never a good idea. You end up hurting yourself as well as someone else. It is best to take the time to reflect by yourself and understand what you need right now. Try not to anticipate and live life for the person you are now, not what you may or may not become.
When you get ready to go out in the morning, look at yourself in the mirror and set an intention. “Today I will be kind” is a perfect mantra to begin with. What you put out in the world will come back to you.
Just realizing you have a new crush can be stressful. Don’t feel like you have to avoid him. If you’re getting butterflies, it’s a sign. When you get to know him better, it will be a relief. Even if you both go out on a few dates and figure out it’s not right, you’ll have a great friend in him. It’s actually very beneficial to have a friend of the opposite sex. You can eventually get comfortable enough to ask for advice in your other dating adventures.
Build your confidence. This is a vague instruction. Set small goals for yourself. If you are really shy this is a great exercise in socializing. Be specific when you compliment someone you don’t know. “I love that scarf, florals are my fave” would be a great start. If you just want to dive in and overcome the fear of public speaking, volunteer at your local library to read to kids. They are really forgiving and you’ve got a ready-made script. Many schools offer public speaking classes, take one. Everyone was new at this once, so it’s no big deal if you trip over your words. You are all there to learn after all.
Getting to know someone as more than a friend is a part of life that will repeat itself over the course of your existence. If you make mistakes, know that it’s okay. We all trip on the path through life but know that it’s not the end of the world if things don’t pan out in your favor.
I was the tomboy in school, who was always seen as one of the guys. Which in one way was great, because I had many guy friends, but I was never looked at as a 
s talking about me. I know the feelings, it's painful when you like somebody so much and they seem unattainable to you. Highschool eventually came to an end and we remained as we always were, friends.