Is He Setting Her Up for a Fall?

A reader sent the following letter. It's a long one, but I'm printing it in its entirety because a lot of women find themselves in the same situation:

Dear Terry:

First, thank you so much for your insightful website and e-mails! They really bring a lot of encouragement.

My situation is this: Several years ago I broke up the biggest loser of all time. I won't go into detail, because he is long gone, but will say that the abuse I endured in that relationship and growing up in a household with a father much like him, definitely took its toll on me. I since have spent a few years in counseling and read dozens of self-help books that truly helped! I am happy about gaining back my self-esteem but still have trepidations when it comes to dating.

After I felt that I had healed, for the most part, I formed a very specific picture in my mind about the man I would want to be with and used visualization daily until three years ago when I met a gorgeous, successful and somewhat famous man , who so eerily fit my picture, and started dating him very casually. He travels a lot and lives in a different state than I so I tried for the longest time to not let my feelings get involved for I was certain that he had women like me in other places. He is very sweet and fun to be with and I know the feeling is mutual. We both admit that it is very passionate, intense and "electric" when we are together even some three years into it.

However, over the past year or so my feelings for him have gotten more intense and I find myself wanting more of a relationship with him. I finally expressed to him that my feelings are growing deeper, and would continue to do so, and that he would need to be honest with me about whether or not he wanted to find himself involved in that situation.

Much to my relief, he smiled a huge smile while I was talking and then said "O.K.". That was it. We have continued to see each other with the same infrequent regularity but he has definitely gotten more personal with me by sharing a lot more about his family and the like and asking many more questions about mine. His text messages even seem more attentive and he also told me (unprompted) more then a few times when we were together last that he had missed me (we only see each other every few months). We were even in contact over the recent holidays which is something he has never initiated before.

I am crazy about him! But I need to know how to move further. I should also let you know that I am a bit intimidated by his success in life only because I am not exactly where I thought I would be at this point in my life.

I have held great jobs in the past but ever since leaving my home state six years after my break up to go back to school, I have had jobs like the one I have now; I'm a sales girl in a department store. I am a single parent solely supporting myself and my daughter and this is not the most lucrative job but the hours are great for working on other areas of my life. Being that I don't have a lot of money makes me a little less confident around him; he's used to hanging out with designer-clad celebrities, and I am used to shopping at Ross and Target, when the rare day comes that I can even afford to do that. I definitely have fashion savvy and like the way I look most often, but have doubts about being with him in public. It is a mild doubt, but clearly not all of my self-esteem issues have been worked out.

We spend most of our time together in gorgeous hotel rooms and have only gone out for appetizers and drinks a few times, but keep in mind that I only see him every few months. I don't really mind given our work schedules are completely opposite and there is truly nothing I would rather do in the limited time we have together then be completely alone with him.

My friends think he should take me out more, especially since he owns restaurants and clubs, and rearrange his very full work schedule to be able to spend more time with me when he is here.

I want nothing more than to be with him on a regular basis, but my daughter is a teenager in high school and I don't think moving is a reality for either of us. I want to get out of the "limited" mindset I am in because I find myself telling my friends "I don't know if I want to get married" or "I think a relationship would just complicate my life right now" - -both statements are far from the truth.

I want to get married!

And I fear that I have blown up in my mind what it is I truly have with this man and have made it into something more than it is- which my best friend says (who is a man, by the way) is just a "good time".

I know this all sounds silly, but I want to make this a real relationship if it has the chance and I don't want my financial situation or moving or anything else to be a barrier to me. Any advice?

-Hopelessly Fallen

Dear Fallen

First of all, congratulations on attracting a man who eerily fits your picture.

That aside, I do agree with you that your self-esteem still needs a little work (although I definitely commend you for the strides you've made after the relationship with the abusive loser).

Your friend suggests that your 3-year-old friendship with the somewhat famous man is "just a good time," and frankly, the man's not giving you much reason to think otherwise. He's texting more and saying more, and he did smile when you told him your feelings, and that's encouraging. But, as the old lady once demanded in the Wendy's commercial: Where's the beef?

He's a successful man who's used to getting what he wants, so what's stopping him here?

You say you feel somewhat outmatched because he's successful and spends time with designer-dressed celebs, while you're a clerk in a department store who wears Ross and Target. Listen, at the end of the day, we're all human beings. We all sleep, laugh, cry, and bleed.

I don't care what kind of clothes you wear. Obviously, you have something going for you, or you wouldn't have attracted this man's attention. As for wearing clothes from Ross and Target, Vogue Editor-in-Chief Anna Wintour has been quoted as saying, "A clever girl can put herself together for a few dollars."

Really, anybody can throw on Prada and (with the right figure) look smashing. It takes a good bit of style to be able to take a so-called lesser brand and make something incredible out of it.

And I have a feeling that's what you're doing.

But, again, I would really like for you to work a little harder on your self-esteem. Make a list of all you have going for you, of all your past and present accomplishments. You are raising a teenager on your own, which is no small thing. Since you had such brilliant jobs in the past, is it possible that you might have achieved stunning success if you didn't have to make the sacrifices that come with caring for another human being?

Give yourself points there.

I do not know this man, and I've haven't seen your relationship for myself, but I tend to agree with your friends. Would it kill him to take you out more?

Yes, it's exciting being with him. It's electric. All those tingly emotions make it difficult to think, I know, but think you must.

You only see him once every few months, but I suggest that when you see him again, you gently suggest you leave the hotel room and go out for dinner. See how he reacts. If he hems and haws, you can joke, "Hey, are you ashamed to be seen with me?"

Again, watch his reaction.

If you don't like it, well, cry if you must, but maintain your dignity and politely tell him goodbye. If he tells you, "Hey, Baby, you know that's not true" and gives you some weak excuse, tell him goodbye.

But if he says, "I really want you in my life. I'd really miss you if you weren't in it," you can say, "Well, I'd really miss you, too, but I'm ready for a real relationship. If you're up for it, don't tell me. Show me."

Put your feelings on the line. Then leave it up to do with them what he will.

I wish I had the magic words to give you to make all your dreams come true with this guy, but please be open to the possibility that he's not the one for you. It's possible he only seems like the one for you because you only see him every three months, and you don't have to deal with his faults on a daily basis.

It's all very romantic right now, but the fact that he hangs out with celebrities and can afford to stay in the best hotels does not make him better than you. See him for what he really and truly is. Determine if he's worth it. Proceed accordingly.

I hope this helps.

-Terry