Q: Hi, I'm a longtime lurker and first time caller. My question deals with the etiquette of online dating. I am a professional in my mid-30s with a terrific career (that probably consumed too much time) and a history of long, rewarding relationships that have for one reason or other not ended in marriage. I moved to a new city for career reasons and decided to give online dating a try. I had previously dabbled in it during down periods before, but never seriously. I did not have high hopes, but sent out a number of emails and ended up meeting two of the women in person. To my surprise, I ended up really clicking with both women, and they both seem to like me as well. We share a number of interests (though different common interests with each woman), and each are attractive, age-appropriate, and successful professionally. By the end of this week I will have had dinner with each of them 3 times (no sex yet, as I would want that in the context of a more committed situation), in addition to getting-to-know-you phone calls and emails with each of them proposing activities we could do in the future of our relationship -- meaning that they are both open to a relationship.
I am starting to feel guilty seeing both of them at the same time, but do not feel that I have more of a connection with one than the other just yet. I also have not yet broached the topic of whether I am one of several guys that they are seeing from the same website or if they are seeing me exclusively. It just feels very strange going from having absolutely no history with someone to deciding that you want to date them after only meeting them three times, but at the same time, I don't want to lead one of them on nor blow it with both.
What are women's expectations of someone who they meet online? How many dates is too many before making a decision?
– Don't Want to Two-Time, Pittsburgh
A: You're right, DWTTT. It's almost impossible to make a decision about someone after three dates. Or even five. Or even ten.
But I'm giving you a five-date limit. You don't have to choose a partner by date five, but you do have to discuss the issue with both women. After five dates, you have to tell them that you're still dating other people, just so they know where they stand. Maybe having the talks will help you make your decision. If Woman A says, "Duh, you're one of six guys I'm dating," and Woman B says, "Wow. I really just want you," you'll have a better understanding of your options. And if you find yourself unwilling to tell one of them that you're dating other people, she's probably the one you want -- the one you're unwilling to alienate and potentially lose.
Of course, these women might beat you to the punch with these talks, so get ready to ask questions and give answers at date four.
Readers? Is my five-date rule for this guy fair? Is he leading these women on? Is it possible that he's really 50-50 about the whole thing? What's the etiquette here? How can he tell them without losing them? Am I right to say that the one he doesn't want to alienate is the one he probably wants? Discuss.
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Meredith Goldstein is a Boston Globe columnist who follows relationship trends and entertainment. She offers daily advice on Love Letters — and welcomes your comments. Meredith is also the author of "The Singles," a new novel about complicated relationships. Follow Meredith here and on Twitter. Love Letters can be found in the print edition of The Boston Globe every Saturday in the G section.