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Real dating disasters (and how to deal with them)

Can't get enough of your friends’ disastrous dating stories? We certainly can’t. So we asked TODAYshow.com readers to write in with theirs, and sex therapist Dr. Laura Berman dispensed some precious advice. From “friends with benefits” to dates who snoop, here are some common dating disasters, along with solutions on how to deal with them.

Q: I was dating for a short time — a 39-year-old banker woman (on a scale of 1 to 10, she was a 10). We had very enlightening conversations, etc. while dating. She seemed to be as smitten with me as I with her. One night after a date, we were back at my place having a nightcap, when I excused myself to the bathroom. I was rather quick, but as I rounded the corner, I caught her going through my checkbook. She didn't see me ... when I returned ... [she was] all smiles. I made some excuse as to not feeling well and escorted her to the door. As customary, she leaned in for a kiss goodnight, and I backed away. I never returned her calls or e-mails and never called her again. I often wonder if she ever figured it out. — Bob, Baton Rouge, La.

A: There is nothing wrong with a little harmless background checking, such as Googling your date or checking out his or her MySpace page. But you are definitely crossing the line once you start rummaging through belongings or snooping into checkbooks! Although I don't recommend prying until you know he's a keeper, if you really need to know something (whether it is about his previous relationships, income, etc.), then you should be upfront and just ask him. But don’t be surprised when he turns the table and asks you the same questions!

If you are snooping and get caught, just be honest and tell your partner why you were snooping ... maybe it's because you think he might be a good fit, but your last boyfriend lied about his finances, or even the hard truth that you like to know the people you are dating are working and not broke. Whatever your reasons, it isn't going to be pretty. Your best hope is that he might be flattered to know that you are so interested in him and let you off with a minor warning.

Q: I recently went on a date with a nice young guy. Initially everything was great. He was a gentleman; we had a great conversation and really enjoyed the time we spent at an exhibition. When it was time to have dinner, he only ordered soup. I felt pretty weird about that so I asked him why, and he said that was all he could afford because he left his wallet at home. Needless to say, I paid for dinner because I felt uncomfortable eating my steak and he was only having soup.

After that night I never heard from him again, and when I finally did see him, he was with another young lady and although all I did was speak to him, he made it seem like I was inconveniencing him. I wanted to say to the young lady, I hope he didn't offer to pay, because you might be washing dishes tonight. — Anonymous, Washington, D.C.

A: Forgo the awkwardness that occurs when the check arrives by agreeing that whoever asks should pay. For instance, if you invited your new man to try a tapas restaurant in the neighborhood, you should pick up the tab at the end of the night. If he invited you, the same rule should apply — regardless of who is pulling in the big bucks. Also, never discuss money on a first date. While it may be evident from your wardrobe or lifestyle that you earn an impressive income, there is no reason to get too specific and start comparing paycheck stubs. If you experience a date such as the one above, simply chalk it up to your date’s social awkwardness and not your own lack of grace — after all, no one should feel guilty about ordering more than a soup on a dinner date! One other possibility is that he goes on so many dates that he's worked out a system where he only pays for the dates he wants to have a second one with!

Q: I let a friend at work fix me up with her son. It was a disaster. He drove fast, cursed at other drivers, and when he saw a rainbow sticker on a car, he launched into a tirade against gay people. I jumped out at a stoplight and called a friend to come get me. I was worried about seeing my friend (his mother) at work, but he apparently just told her it didn't work out. — Karen, Liberty Hill, Texas

A: Bad fix-ups happen to everyone at some point or another, and it is not necessarily anyone’s fault. For whatever reason, sometimes people just don’t click! If this is the case, simply confess and tell your date that you would rather just be friends. You don’t have to remain on a date from hell, but try not to storm off unless absolutely necessary. If your Cupid asks you how it went, tell her that it wasn’t a love match, but you appreciate her effort. If she keeps hounding you about it, remain aloof and remember not to take her hook-up offers in the future.

Q: I have been hooking up with my male best friend. When we're not between the sheets, we act as if nothing ever happened. I am not currently seeking a formal commitment, but I would like to discuss some ground rules or something, and what he thinks of all of this, because he and I grew up together and I could not bear to lose his friendship. Help! — Adry, Miami, Fla.

A: “Friends with benefits” situations are becoming very common. These rarely evolve into successful committed relationships, so men and women should be prepared for the possible ending of the sexual relationship and the possible ending of the friendship. Ten percent of friends-with-benefits relationships result in losing the friendship (and the sex) in the end. Furthermore, if this guy is your best friend, you already like his personality. Add to that the oxytocin (the chemical of attachment) that washes over your brain with orgasm, and you are very likely to end up falling in love with this guy. So proceed with caution.

Ground rules are very important if you are going to proceed with a friends-with-benefits relationship. They can help prevent hurt feelings and keep everyone’s expectations on the same page. For instance, it is important to set rules such as: Are you two exclusive, or can you sleep with other people? If so, is this sex safe? Are you expected to stay the night after a sexual encounter, or is it OK to have a “wham, bam, thank you ma’am” situation? Is there a possibility for a relationship to develop from this? All of these questions need to be answered and understood by both parties, otherwise heartache may follow.

Dr. Laura Berman is the director of the in Chicago, a specialized health care facility dedicated to helping women and couples find fulfilling sex lives and enriched relationships. She is also an assistant clinical professor of OB-GYN and psychiatry at the Feinberg School of Medicine at Northwestern University. She has been working as a sex educator, researcher and therapist for 18 years.

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