I'm an 18-year-old guy that's been in a long distance relationship with an older (mid 20's) guy for a month now. We either Skype or talk on the phone every single night. He is the first person I have started a relationship with since I came out and so far, everything is great! We tell each other about how our day has been, work around each others schedules to be able to talk whenever and express how much we really care for each other and how "it was meant to be." I've started planning a trip to fly out and see him in a few months and we talk about all the things we are going to do which includes everything from outdoor activities to having sex, which will be my first time. He understands that and promises to take it easy the first time, but he is a very horny guy and I know he will be expecting a lot of sex and, of course, I don't want to disappoint him. I need to know if this is too much, too soon. Should I wait longer? He is concerned I will start college and be exposed to other gay men and forget him. A friend told me that I'm just falling for the first person that shows me attention, but we really have a good connection and I want it to be the right thing to do.

Flustered And In Love

My response—and FAIL's response to my response, and mine to his, etc.—after the jump...


Where does Mr. Mid-20s live? Where did you meet him?—Dan


Out of all places, he lives in Iowa. I'm a 12 hour drive away from him. I met him online, and talked a lot on there and finally exchanged numbers and Skype addresses.—FAIL


Where in Iowa?

Basically, FAIL, I'm curious as to why Mr. Mid-20s is talking to teenagers online who live 12 hours away instead of meeting gay men closer to his own age in the city where he lives. I'm not saying he's a bad guy, or that you're not super special enough to fall in love with via Skype, but this looks like a red flag to me. You would have to approach your first meeting as if you're meeting a stranger. Because you will be, FAIL.—Dan


He lives in Iowa City and goes to school there. I understand that it sounds skeptical because I've never met him, but I'm a smart guy and I feel safe about him. He says that there are no decent guys for him in his area and only older guys hit on him. I guess my main concern is that I'm new to this, and it seems unreal to have found my perfect guy on the first try. Although, in the back of my mind, I kind of do want to go to college and experience life without being tied down, but he says I'm one of the greatest things to happen to him in a long time (which I believe after hearing about his past relationships) and it would crush him if I broke it off.—FAIL


If Mr. Mid-20s can't survive the demise of a month-long relationship with someone he hasn't met in person—and I'm not that I'm saying your relationship is fated to end—he's not emotionally mature enough to be in a relationship with you or anyone else.

Look, FAIL, the odds that you've met your life partner, at age 18, online, are pretty slim. I'm not saying you haven't. I'm just saying... be realistic. And don't go into this thinking it has to be a love-of-your-life/met-the-perfect-guy scenario for it to be worthwhile. You could meet Mr. Mid-20s, have a romance, learn, grow, realize he's not everything you want or that you don't want to be tied down right now, then part as friends—and it will still have been worth your time. Scale back your expectations, FAIL, and you're less likely to be devastated if this doesn't work out.

And now a few bewares: Beware of guys who pressure you into making premature commitments. Beware of guys who want you to commit to them before you've even met in person. Beware of guys who tell you that you're the greatest thing that's ever happened to them when, technically speaking, you haven't happened to them yet. And beware of guys whose past relationships have all been disasters as they're the common denominators in all of those disasters. (He's a 20-something college student in a college town... and there's no one on campus who'll date him? Why is that?)

But if you want to meet him, go and meet him. You're an adult. But tell people where you're going and who'll you be with. (Maybe you can make it a road trip/adventure and your friend can go with you?) Verify that you have his real name and real phone number. Have your first meeting in a public place. Have someplace to stay besides his place. If you meet him and you like him and you want to have sex with him, USE CONDOMS if you decide to have anal intercourse—and you don't have to have anal intercourse to have sex.

Take it slow, FAIL, and watch out for red flags. (Here's another one: you haven't even met this guy and there's pressure about his sexual expectations and you're worried about your sexual performance. He's in love with you, he says, and you're a virgin—you're the one whose needs and expectations should be paramount.) And if you sense he's rushing or pushing you to do something—anything—that you're not comfortable with or ready for, or you just get a general bad feeling about him, or if it's clear that he lied to you about himself, GET THE FUCK OUT OF THERE.—Dan