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Dear Dr. Goodheart:

I've read a lot about crushes online.

I have had a crush on my Boss for the last year. I fear rejection and embarrassement. I know to pray and let the Lord work... yet... I wonder. I'd have to find a new job. I like my job, for once, and it's not primarily because of him.

I flirt with him and he seems receptive. He treats us all with the same attention and respect. We're about the same age, he's 34 and I'm 32. Neither of us are married, nor do we have children. Us girls in the office sometimes get the feeling he could be gay, but I just can't imagine that.

He's kind, respectful, mature, brilliant, funny... I adore and respect him very much.

I figure that I'd rather be around him 8 hours a day, than take a chance to tell him and then maybe never seen him at all.

So, what do you tell gals like me ?

Sincerly,

Cinnamon
Good Year, AZ

Dear Cinnamon:

Business flirting is always, pardon the pun, risky business, especially when power hierarchies are involved. It's no easy thing flirting with your boss, or vice versa, which is probably why this unbelievably charming man has come off more "gay" than Rico Suave; in other words, your boss is probably well aware of the dangerous politics involved in business liaisons and as such, has kept his relations casually charming at best. If you are interested in this man, but completely unsure as to how he feels about you, personally, I would probably advise you play it cool. What with "sexual harassment" dangers, and the issue that he is your boss, you may want to wait and see how he responds to a slightly more "friendly" you, but I wouldn't advise upping the flirting ante any further.

If, however, you are determined that there is chemistry between you two, you may want to approach him in a bit more obvious manner; to be fair to his precarious position as your boss, however, you may want to make it clear from the beginning that your being interested in him is in no way intended to disrupt the business, and consequently, if need be, you may want to let him know that you have been "job searching."

As a matter of fact, you may want to start that "job hunt" now and see what's out there, that way you've carefully calculated the risks involved in possibly pursuing something with this man. Coincidentally, it also allows some cushion time to gauge his reactions as you begin acting a little more personable than say, the other women in the office. Either way, be sure your actions don't compromise the tenuous business relations of your company.

Best of luck,

Dr. Goodheart, Flirting.com.

Dear Dr. Goodheart,

I have been in an off and on relationship with someone for a little over a year now. I don't like being single at all. Whenever we break up, I miss him a lot and I always want to talk to him. But when we are a couple I kind of get sick of him. He is always stuck in the house and I don't really get to see him that much. I used to see him every weekend but lately I haven't been going to see him. He tells me all the time that he loves me and I used to say it back to him. Now I just change the conversation and act like I didn't hear him because I don't like to say it back to him anymore. What do I do when I don't want to be single but I don't want to be with the person I am with anymore?

Also, I am usually nervous when I talk to some one that I like. Usually the people that I like don't even know that I like them. I usually just wait for them to come to me. I fear being rejected. After I tell someone that I like them, I feel so weird in front of them. Mostly when they turn me down. I can't even remember the last time I asked a boy out. I am too shy. How do I overcome the fear of being rejected ?

Last but not least, there is this kid who goes to school with me who I think is very cute. I only see him every once in a while in the hallways but we don't talk. I know his name cause someone told me but he doesn't even know my name. We never even said "hi" to each other. I have thought that this kid was cute for about 4 years now. Only 2 of my friends know that I think he is cute but neither one of them have ever talked to him. I want to start talking to this kid so that I can get to know him better and so that eventually we can start going out but I don't know how to let him know this. What do I do ?

Please help me with all 3 of these !

Paula's Problems

Dear Paula's Problems,

It's never easy being alone, trust me, I know firsthand the pains and psychological pressures of feeling like the "only single girl" left on the planet. I went through the awkward periods of either being the “third wheel” to my friends and their significant others or I dated guys that everyone, including myself, knew were bad for me. I was always the quintessential "girl you marry," not the "girl you date"; in other words, I was single most of college, dating only ever sparsely, and casually. Still, though, it wasn't easy. Though I cried myself to sleep many a night, in the end, I was glad that I chose to ditch the playboys, opting for solitude until Mr. Right walked through the door (literally, my husband to be, ironically, is a Mr. Wright !).

Moral of the story: it sounds like you are definitely not that into this guy; that you are questioning wanting to be with him right now, with no thoughts of marriage or a long-term future in store suggests that he probably isn't the one for you. In that case, you owe it to yourself, and this guy, to be honest and end the relationship before things get even more precarious and confusing; the longer you wait, the more complicated a break up will get. What’s more, that you have had your eye on a certain someone else, namely the 4-year crush, only further confirms that your current significant other is not the right guy for you. Though it won’t be easy, though you may run the risk of being alone, though this new guy may not want to jump into a relationship with you, in the end, I promise that letting go of your current guy is the best thing you can do for yourself.

As for the 4-year crush, I suggest you give yourself some time being alone; learn how to like being an independent woman; people often find they learn a lot about not just themselves, but also what they want out of a partner, while they are alone, namely because they have time alone to reflect on such things. Hopefully, time away from your current partner will help shed light on whether or not this other crush is the right guy for you; the time alone may also bring you the opportunity to scan other possible alternatives in the dating pool.

I know you said you are shy, but most people are. Still, that doesn't mean that your being shy should paralyze you into "settling" for someone that's not right for you. If you know you're "over" your current partner, move on and allow yourself some "solo time" for a potential epiphany. Who knows what moments of clarity are to follow?

Best of Luck,

Dr. Goodheart, Flirting.com.

Dear Dr. Goodheart:

I am an 18 year old guy. I have a problem of low self confidence as a result of which I am unable to have a good interaction with girls in my college. I am not one of those guys who have a good sense of humour neither do I have those interests about which I can chat with girls. I have many male friends but unable to make female friends. Please help me, I am in a desperate situation.

Thanking you,

Ankur

Dear Ankur,

Like most young men, you are going through a period in life where you have to juggle personal, professional, and academic schedules; often, the first of these three takes the biggest hit, specifically in the "romance" department. When people are just starting out as young adults, trying to figure out what they want out of life and who they want to spend that life with, they're often surprised to discover just how difficult juggling an intimate relationship and a social life can be, especially when school and jobs are mixed into the equation. Instead of hiding behind your "shyness," and instead of trying to be that charming "clown" that attracts girls with your humor, allow yourself this "single" time to find yourself.

Don't rush into relationships simply because you don't want to be alone. Like "Paula's Problems" (see above), I would suggest to you that this time of solitude is a gift (though it probably doesn't look nor feel like one); instead of getting frustrated by your single status, pour yourself into your social life, even if it means hanging out with the guys. Most all single guys in college are looking to hang out with girls anyways, no matter how "shy" or "socially inept." The main way(s) they aspire to acquiring a "girl" posse is to either hang out at the bars and/or join a club or group relative to their major and/or personal interests: church, chemistry club, etc. This is probably going to be the "shy guy's" and, consequently, your best segue into the world of women, significantly, women with whom you potentially have something in common. If you really want to get involved in a social network that includes members of the opposite sex, I would recommend getting involved in either a religious organization and or school club; get involved with their events, like weekend potlucks, meet-and-greets, after service socials, or weekend community service projects. I'm willing to bet that you'll be surprised to see how many quiet, nice, "shy" people like yourself are searching for the same thing you are, they just do it under the guise of group outings and community service. Not surprisingly, the added advantage of these organized activities/outings is that they break the awkward ice of the "dating" atmosphere because people are just as interested in participating the coordinated events (or should be) as they in getting to meet other people and members of the opposite sex. If nothing else, you'll have some fun building your résumé in the process.

Best of Luck,

Dr. Goodheart, Flirting.com.