Kevin Richberg, a 32-year-old gay man (and good man) from Boston, is looking for the love of his life. He’s picked an unusual way to find him.

Interview conducted by Benoit Denizet-Lewis:

Benoit: Kevin, you and I went on a date a few years ago, although it consisted mostly of us drinking wine and making out on your couch. You’re being a bit more creative this time. In October, you’re getting in your car, driving around the country, and going on thirty dates in thirty days. Oh, and you’re blogging about it all. What spurred this on?

Kevin: Well, I was in India over the New Year, driving from city to city every day, and when I returned I realized that if I could do such a crazy adventure in India, the States should be simple. Then I noticed I was single, and the idea just sort of came to me organically. And, hey, the idea of going on some fun dates appeals to me.

Benoit: So you’re saying our date wasn’t fun?

Kevin: (Laughs) Not at all! Drinking wine and making out on a couch can be a fun date, but this particular journey lends itself to having the city itself be an integral part of the date. I’m actually hoping that these dates follow the traditional plan of two people who have never met and who want to get to know each other in a memorable setting.

Benoit: But is that really the traditional path? Isn’t it more traditional to drink and make out on a couch, or go out to a restaurant and stress about who will pick up the check? I have friends in their twenties who insist they’ve literally never been on a formal “date” in their lives. Are you trying to bring back the date?

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Kevin: I’m just trying to have an adventure, and possibly meet my soulmate.

Benoit: Tell me a bit about your dating history.



Kevin: I actually haven’t been on many traditional dates. My previous boyfriends have all come into my life through odd and strange ways. Usually the folks who have asked me on what I’m considering “normal” dates have turned out to be uninteresting boobs. It’s my hope that this adventure changes that.

Benoit: You’re asking the men who want to go on a date with you during this trip to propose ideas for how you’ll spend your time together. What’s the most unusual proposal you’ve received so far?

Kevin: Well, other than the purely sexual ones, which thankfully have been few and far between, one gentleman wants to take me on a foreclosure tour of Detroit, looking over all the abandoned properties. Not exactly the most romantic idea ever.

Benoit: Yeah, that’s kind of dark, but it’s a perfect lead-in to my next question: Will you be doing background checks on these people? I worry about you.

Kevin: The proposal itself is designed to weed out anyone that might be “dangerous,” but no I won’t be doing any sort of check on anyone. And fortunately I’ve received plenty of great proposals from what seem like perfectly nice people. Probably the most romantic so far is a man from Oklahoma City who wants to cook me a six-course meal, something that would not normally seem all that special, except he proposes to do it around the entire city like a culinary tour of OKC. I’m not sure how he would even pull it off, but the way he describes it is very genuine.

Benoit: I noticed on your web page that you’re not requiring prospective guys to include a picture of themselves. That’s very noble of you. Why go that route?

Kevin: This is very important to what I’m doing. I purposely wanted to open myself up to new kinds of individuals, so I’m taking the “superficial” out of the equation. I’m betting that I can see into a person through ten questions well enough to determine who would make a good match for me on a first date. It also allows guys online who are worried about their looks to take a deep breath and just be themselves without all the posturing that often comes from trying to “choose the right photo” of themselves.

Benoit: Yes, that can be exhausting. Will you know the ages of the guys who are proposing dates? Could your soulmate be a 65-year-old man, or an 18-year-old boy?

Kevin: I won’t know the ages, but that’s a part of the self-correcting nature of the process itself.

Benoit: What do you mean by that?

Kevin: I’m trusting that folks won’t go through the whole process of proposing unless they believe it’s the right thing to do.

Benoit: I like to think that I see the good in people, too, but in this case I think you might be bat-shit crazy. I know some 18-year-olds who would definitely think it’s the right thing to do to ask you out on a date.

Kevin: I’ve already had many 18-year-olds say to me, “I’m too young.” And a 65-year-old man who genuinely in his heart believes that this is not a possibility for love won’t go through the trouble of filling out the proposal. And even though I have no way of proving it, I believe the average age of proposals is actually my age.

Benoit: How many proposals have you received so far?

Kevin: 350.

Benoit: Well, hopefully you’ll get a few more after this article. How have you gotten the word out?

Kevin: Gay sites like gay.com, adam 4 adam, manhunt.

Benoit: Manhunt is an interesting choice, because the site is clearly mostly about sex on demand, but there are a number of men on there who swear up and down that they’re on there looking for their soulmate. I’m not sure how one can recognize one’s soulmate amidst the haystack of penises and chest pictures, but that’s a discussion for another time. Let’s talk the logistics of your trip. What you’re planning isn’t the easiest thing in the world to pull off. You’ll be driving across the country (which is tiring enough), but you’ll also be going on a date every day. How long will these dates last?

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Kevin: The schedule is designed so that I drive four to six hours in the morning and then give each individual a max of twelve hours to “date” with.

Benoit: That’s way too long for a date.

Kevin: Well, realistically, since a great many of these dates will be happening on weekdays, it’s inevitable that some guys won’t be able to meet until after work, so that will shrink the window to a date of maybe three to six hours.

Benoit: Do you have any rules about sex on these dates?

Kevin: Yes. There’s not going to be any sex on these dates. They are going to be traditional first dates, with at most a goodnight kiss at the end.

Benoit: So it won’t be like our date then?

Kevin: Exactly.

Benoit: What if your car breaks down and you can’t make a date and it messes up your whole thirty in thirty schedule?

Kevin: I’ll be driving a Toyota Prius, and hopefully Japanese engineering won’t fail me, but if per chance it does, I have AAA.

Benoit: You probably travel more than any person I’ve ever met. Honestly, I’m not sure how you managed to complete your master’s in marine biology from MIT with all the traveling you do. Not to psychoanalyze you, but let me psychoanalyze you: Even if you do find the man of your dreams on this trip, are you ready to settle down? Can you be truly happy in one place, with one person?

Kevin: One thing a lot of people don’t know about me is that I very much want to have a family. I am the son of my father, who was absolutely a family man. So when I find the right person to settle down with, I’ll definitely turn from crazy travel adventurer into wild and wonderful husband and dad.

Benoit: Kevin, you are a handsome man. Do you think you would have put yourself out there in this way if you weren’t, or if you weren’t comfortable with yourself? Because I suppose it would be a very sad thing for someone to organize such a trip and then get very few requests for dates.

Kevin: Honestly, I would not have done this if I wasn’t comfortable with myself, or if I thought that no one would want to go on a date with me.

Benoit: What do you look for in a guy?

Kevin: Now, if I told you, that would be cheating! I’m not going to bias the possible dating pool by saying I like this, or I prefer that. So, for now, I’ll just say I’m open to all possibilities.

Benoit: So, if someone out there reading this wants to be one of the lucky thirty who gets a date with you on this trip, what do they do?

Kevin: They go to the web site and click on “proposal.” Then they get creative.

UPDATE FROM THE ROAD: Wondering how it’s going? 21 days into it, Kevin gives us this update.

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