Dear Wendy: “My Boyfriend Still Frequents A Dating Site”

OK, whoa, sorry for posting that fake letter yesterday. Man, you guys took me to task on that one! That’s OK — I can take it as well as I can dish it. And to make it up to you, I’ve got two (very real) letters today. Read on…

My boyfriend and I have been together for going on five months now and things on the whole are going great. He’s super sweet, thoughtful, kind, and affectionate, genuinely enjoys spending time with me, and even at this early stage he’s hinted to me that he can see this relationship continuing for a while. The problem is we met on an online dating site and he’s still listed as single on there. Not only that, but he still logs in pretty frequently (about two or three times a day). Admittedly, I go on there quite a bit too, but I’ve been listed as “seeing someone” for about a month, so there’s no ambiguity about my only being there for a little “window shopping,” if you will. I know he’s not seeing anyone else — I trust him, and frankly, I don’t see how he would have the time anyway. But I’m just worried that deep down he thinks I’m not enough for him and that he’s hoping to meet someone even better. We joke about the site all the time and tease each other whenever one of us happens to see that the other has gotten a new message, but there’s this tiny part of me that’s worried that he’ll actually act on it. I know this is a really stupid and petty thing to be worried about but somehow I can’t let it stop bothering me. How can I ask him about this without seeming super clingy or like a web stalker? Or should I just try and forget about it? — Well-Matched

Actually, WM, I don’t think your concern is “stupid” or “petty” at all. It’s a legitimate worry and one that should be nipped in the bud right away. I’m not sure how serious you two are or how often you’re seeing one another, but if you’re calling the guy your “boyfriend” and you say you’ve “been together” for five months, I’m confused as to why either of you is still on a dating site at all, let alone checking it frequently. If both of you are truly into this relationship and each other, you really shouldn’t be doing any active “window shopping,” as you call it. At all.

You need to be honest with yourself here. Are you into this guy enough to delete your profile and quit keeping an eye out for something better? Because if you aren’t, you can’t very well question why your boyfriend isn’t ready to do the same. If you aren’t willing/ready to delete your profile, you’ve got to accept that he’s in the same boat, and perhaps now that it’s been five months, you need to evaluate whether you really do see this relationship moving anywhere.

If, however, you’re ready to truly commit to your boyfriend and take yourself “off the market,” so to speak, it’s time to have a heart-to-heart with him about this. Tell him that at this point in your relationship, you’re uncomfortable with either of you being on a dating site any longer. It isn’t “clingy” to ask a boyfriend of five months to quit trolling for other women online. If he isn’t willing to stop, you might want to change your profile back to “single.”

I’ve been with this guy for five months, everything’s great, I’ve met the family and all that. But apparently not all of the family, because both my boyfriend and his family have mentioned an older brother, “Bill,” who as far as I can see is no longer part of their lives. It’s not that I want to pry, but I get the feeling this will be painful to explain if and when he opens up to me about where Bill is now, and I have absolutely no idea what I’d say in that event. Any guidelines for conversation you could offer would be appreciated. — All in the Family

Asking your boyfriend of five months about the absent brother his family keeps referring to is not “prying.” It’s showing an interest in his life and it’s not only normal, but totally appropriate. I respect that you want to be sensitive to a subject you think might be touchy, but not mentioning the pink elephant in the room is probably a lot more awkward for your boyfriend than if you just came out and asked about him. Not only that, but it’s kind of keeping you from being as close to your boyfriend as you could be. Revealing intimate parts of our lives and sharing vulnerabilities is how we create bonds with people. It’s one of the ways we show our trust. By avoiding a topic you’re afraid might be painful, you’re missing an opportunity to show your compassion and prove your trustworthiness.

The next time you’re having a low-key time with your boyfriend, just say to him, “Hey, this might be kind of a sensitive topic, but every time we’re with your family and they mention ‘Bill,’ I’m a little confused because he isn’t someone you’ve really talked about. I hope you know you can trust me enough to tell me about him.” At that point your boyfriend will either open up to you or tell you he isn’t ready to talk about it yet. If he opens up to you, be a good listener and let him do the talking. When he’s done, thank him for being honest and trusting you. If he isn’t ready to fill you in yet, don’t press him; tell him you care about him and you’re there to listen whenever he’s ready. If nothing else, opening the lines of communication will show you care, and make it easier for him to broach the topic later.

*Do you have a relationship/dating question I can help with? Send me your letters at [email protected]