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Reading the Situation
Talk to her about her boyfriend. If the boyfriend is one of your close friends, then yeah, it's a very good idea to back off unless you want to ruin your friendship. But if you don't know who the boyfriend is and want to get a sense of her relationship with him, then you can try to slyly get a sense of her relationship and how serious it is without prying too much. Here's what you can say: "What are you up to this weekend?" "How long have you been with your boyfriend?" "I had a girlfriend, but we broke up a few months ago. It was hard, but I feel much better about it now."
See if she's happy in her current relationship. Though you can't just come out and ask her if she's happy, you can get a sense about it just by talking. Basically, if she complains to you about her boyfriend all the time then that is a strong sign that her relationship is not looking so good. See if you can get an idea of how she's feeling just by making casual comments and seeing if she responds in the negative or affirmative. Basically, you don't want to try to get with a girl who is in a great, or a particularly long, relationship; you don't want to deal with the emotional baggage even if she does decide to end things. Say, "It must be nice to live with your partner. What's that like?" Or say, "You've been together for two years? That's a pretty long time…"
See if she's even interested in you. Before you step further, see if the girl even cares about you in a romantic way. Read the signs. Does she go out of her way to talk to you? Does she light up when you walk into the room? Does she make excuses to always be at your side? Does she even flirt a little bit? If so, then yeah, there's a good chance that she may have a crush on you. Here are some other ways you can see if this is the case: Talk about other girls in front of her. Without being too obvious about it, see if she gets jealous. Give her a compliment or two. See if she gives one back later.
Don't get stuck in the Friend Zone. If you want to get with the girl, then you can't turn into her best friend, the guy she can come to with all of her problems. Though talking to her about her boyfriend and relationship in the beginning can be a good way to get a sense of what's really going on, the last thing you want to do is to be the guy who she comes to with a carton of Cherry Garcia at midnight so she can cry about her communication issues with her boyfriend. You want to be seen as another romantic prospect, plain and simple, not as her new BFF. Though you do want to be seen as a romantic prospect, that does not mean you want her to see you as a sharper, snazzier, version of her current boyfriend. She should see you as someone completely new, refreshing, and exciting, not as another guy she can take to the movies and hold hands with. If she starts complaining to you about her boyfriend issues, say, "Hey, you can save that stuff for your best friend. I just really don't want to go there, okay?"
Know which girls are just not worth talking to. If you want to talk to a girl you like who has a boyfriend in the hopes of breaking up her relationship and having it lead to something more, then you should make sure you're talking to a girl who is worth it, a girl who is really interested in you and not just with flirting with you and then coming home to her boyfriend. Here are some girls to avoid: The girl who lets you take her out to dinner and the movies only to go home to her boyfriend. Don't take her out like you're her boyfriend unless you actually are her boyfriend. She may just be using you for free food and drinks. The girl who flirts with you for months but doesn't let it go anywhere. Don't be with the perpetual flirt, who just likes to get attention from guys and nothing more. The girl with the crazy boyfriend. You do not want to get mixed up in that. The girl who is just looking for a guy-pal. (See above about avoiding the Friend Zone at all costs). The girl who is just using you to make her boyfriend jealous. Stay as far away as possible.
Making a Move
Treat her with respect. If you want the girl to like you, then you have to be respectful of her, and of the fact that she has a boyfriend. Don't make jokes about the boyfriend, be sleazy, always try to put your arm around her, or say demeaning things about the boyfriend or her relationship. If you really want her to like you, then you have to treat her like a lady. You can compliment her but don't make it look like you are perfectly OK hitting on a girl who has a boyfriend; let her start to see that there's something special about you. Even if she is entertaining the idea of being with you, nothing will put it out of her mind faster than if you blatantly try to hook up with her.
Let her make the calls. Get her to the point where she really likes you and wants to spend more time together. Mention a movie you want to see and see if she asks to come along. Tell her about a party you're throwing and see if she'd like to be there. The ball should be in her court so she can make these decisions on her own and not feel like you're putting too much pressure on her. Play a little bit hard to get; you have a lot going on and plenty of girls who want you, and if she's interested, she should get in line. Letting her realize how awesome you are just by being your charming self is better than degrading yourself by begging her to hang out with you when you know she is taken.
Find a way to hang out. Whether you're studying together, going to the same party, or just randomly ending up at a cafe after class, make sure you spend some time with her. Don't just flirt over text or send her Facebook messages if you actually want to get somewhere. If you think it would be too weird to hang out alone, hang out with her in a group setting first. But try to get her alone when you can, so she can start thinking about you in a romantic way, and really noticing the fact that you two have a lot of chemistry.
Make her feel special. Let her see that you see something unique in her, and that you're not just trying to get together with her because you think she's hot. Compliment her hair, an aspect of her personality, or her ability to work so hard in school. You shouldn't hit on her, touch her, or be too obvious about it, but you should let her know that you really see something in her. If she has a feeling that you really have a sense of the amazing person she is, then she will start to see that you may be the right guy for her. Show her that you really care about what she thinks. Ask her what she thinks about your new shoes, your chemistry teacher, or a new band you like. Let her see that you really value her thoughts.
Let her see that you're interested. You don't need to spell it out for her, but you should let her see that you view her as more than a friend. You can do this through compliments, suggestions that you really care about her, or just by making eye contact and standing close to her when you talk. Here are some things you can say: "I think your new haircut really makes your eyes stand out. It looked great before, but it's even prettier now." "You're one of the only girls I've met who loves sports and who is really fun to talk to about almost anything. That's so cool." "I really feel like I can talk to you about anything."
Show her how awesome you are. You shouldn't have to fake it to impress the girl and make her see that you're a guy worth knowing. Stay modest while letting her see that you have potential, that you're smart, cool, talented, and interesting and someone who would be perfect for her. Just be your best self without feeling like you're being dishonest. Open up to her about the things that matter to you. Just make sure that she's also opening up. After you tell her something that might be a bit private, you can say, "I haven't talked to anyone about that in a long time. It's just so easy to talk to you, for some reason."
Be refreshing. Remember what we said about how the last thing she wants is another guy who is exactly like her boyfriend? Well, it's absolutely true. Be spontaneous. Be fun. Don't call or text her every five minutes just to "check in". Come up with something completely random and fun that you can do together. Give her an original compliment or a funny little gift. Ask her to dance in the middle of the street. Just do whatever a normal, boring old boyfriend wouldn't do. Make her feel alive every time the two of you are together. Don't be afraid to talk to her about something that you think may be a little random if it's funny or interesting. You don't have to fit any kind of mold.
Be persistent (without being annoying). This is a delicate balance to find. You want her to know that you want her without coming on too strong or always being up in her grill. Talk to her at parties, walk alongside her after class, but do not become the guy that she can flirt and have some fun with before she comes home to her boyfriend. Be around, let her know you're interested, but also let her see that you won't wait around forever for her to make the call.
Get together with her. If you just flirt around with her for months, she'll think it's perfectly okay for her to have a guy to flirt with and a guy she is dating. Well, that's not cool, and the longer you go for this, the more she'll see that she can string you along without ever making a move. So, it's time to make a move, have her respond, or get her to make a move already, whether it means kissing you and getting with her boyfriend. Ideally, of course, she'll break up with her boyfriend and then get with you. Seriously, the sooner this can happen, the better. If you've been flirting around for over a month, chances are, she'll never make the break.
What to Do After You Get Together
Take it slow. So, you've snagged the girl, she's dumped her old boyfriend, and now you've finally gotten what you want. Does this mean you should go shopping for engagement rings or take a weekend trip to the Bahamas? Absolutely not! Even if the girl got out of a bad relationship, it's likely that she's still going over the break up, so give her some time and space. If you try to hang out with her every second of every day, she's likely to feel overwhelmed and to back away. Instead, give her space and hang out with her once or twice a week, or however many times she's ready for. This is something people don't get: break-ups are always painful, even if you're the person who did the breaking up. You may think that she feels totally free and happy because she got rid of the dead weight in her life, but she'll still be dealing with pain, and the inevitable grief that comes from saying goodbye to something, even if it wasn't all that great, and you have to be understanding of that. Though she shouldn't be the one to call or text you every time, make sure to give her some of the power. If you're the one who initiates contact every time, she may think that she's not ready for another boyfriend or for anything serious.
Avoid talking about her ex-boyfriend. Whether she got out of a three month relationship with a real jerk or a five-year relationship with a nice but boring guy, you should never bring up the guy, especially if you want to make fun of him, call him a loser, remind her that he wasn't good enough for her, etc. Though your intentions may be pure and you may just want to make her feel better about ending something that wasn't working, she may take this as an assault on her former relationship, and may be offended, because it's likely that she still has tender feelings for her ex. Give it time. If she was in a five year relationship, then yeah, she may not be ready to talk about that part of her life for a long time. Maybe even a year will pass before she brings up her ex at all, because it will hurt too much to do it before hand. Be patient. If you keep asking questions about her ex, you'll come off as jealous and she'll get annoyed. Yeah, there may be this whole part of her life that you don't have access to for a while because it has to do with her ex. Nobody said snagging a girl with a boyfriend was easy, or that it didn't have consequences. But if you wait out this painful period, it'll be worth it.
Don't get paranoid. Okay, so you grabbed a girl with a boyfriend, and only now does it dawn on you -- if she was able to cheat (or just emotionally cheat) on her boyfriend with another guy, then what will keep her from being unfaithful to you with the next guy who comes along? Well, hopefully she got out of her last relationship because it was truly bad and because she saw something special in you, not because she was generally restless. If she has a pattern of this behavior, then that is something to worry about, but if not, unfortunately, the heart does wander sometimes if it's worth it. Your job is to focus on your new relationship instead of worrying that she's seeing someone on the side; if you're constantly jealous and paranoid because of the way that you met, then your newfound love will never wok. If she just got out of something serious, the last thing she may want is to feel like she's smothered all over again and can't go more than ten minutes without checking in with you.
Get a fresh start. So, the two of you are together, maybe even officially dating. Sure, you might have met in a somewhat sketchy way, but that doesn't mean you have to bring it up all the time. Focus on what's ahead of you instead of looking behind, and work on building a solid foundation for your love, not one that's based on lies, deceit, and uncertainty. Even if you had a rocky beginning, you may be able to form a strong bond, though yeah, it'll be tougher than if you were just two single people who met at bar. If you do want it to work, focus on the things you will do together, instead of any of the pain that is behind you. This doesn't mean you can never talk about the period when you were getting together on the d/l. But it does mean that you should focus on all of the great things ahead of you, not on the pain that you might have felt in the beginning. Find new things that neither of you have done that you have always wanted to try, whether it's making your own sushi or going on a long hike. Find things you can claim as yours and that you can use to build a solid foundation for your love. Then just sit back, relax, and enjoy the ride!
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